Next Mile M&A
Next Mile M&A · Powered by Black Belt TC®

Revenue Execution Engine
Playbook.

Issue Vol. 3 · No. 2
Leadership June 10, 2026
For Wally · Mike · Ron · Jay
Inside · organized in three layers
Phase 1 · The 90-day work

Instant Clarity.

90-Day Revenue Execution Sprint.

The first picture — the math, the customer voices, the three audiences this playbook is built around.

In this layer: Contents · Overview · Sellers · COIs · Buyers

The framework underneath

Bloom Growth Operating System.

Eight essentials of a healthy growth business.

The operating system both phases sit on. The framework that organizes how the leadership team works against what matters most.

The 8 Essentials: Growth Plan · People · Sales & Marketing · Meetings · Finance & Data · Process · Technology · Elevate Relationships

Phase 2 · The ongoing rhythm

Constant Clarity.

Continued team alignment and accountability.

The cadence between meetings — the working list, the playbook itself, the record of what we’ve decided.

In this layer: The Meeting · The Playbook · The Record

For the Revenue Leadership Team

How to use this document.

Each of you owns a specific use of this playbook. This is the working version — not a reference document. If you’re using it right, it gets sharper every two weeks because of what you put into it.

Owners · Sales Meeting

Mike, Wally & Ron.

Process · Pipeline · Conversations
  • Live the Sellers section. Mark up the mindset and scripts at each stage — your fingerprints are missing.
  • Record every external sales call. Push the file to Dan after.
  • Update deal stages in HubSpot as soon as they shift.
  • Walk real deals through stage spreads in the meeting. Push back where the doc is wrong.
  • Use the matrix as your COI credibility piece — show outsiders the 11-stage journey and where their referral plugs in.
Owner · Tech & Approvals

Jay.

Vendors · HubSpot · AI · Approvals
  • Approve vendor and tech proposals. HubSpot, Claude, CRM tooling — the sign-off comes through you.
  • Read Records · Section F (CRM Build). What’s been spent, what’s shipped, what’s next.
  • Own tech infrastructure decisions. Portal strategy, AI direction, HubSpot architecture.
  • Unblock the team. Wally’s Chrome/Edge issues, Mike’s transcript access, anything tech that’s slowing deals.
Owner · Facilitation

Dan.

Ingestion · Synthesis · Cadence
  • Ingest call recordings shipped between meetings.
  • Refine the document based on what’s actually being said.
  • Surface new O&Os from the cadence.
  • Ship the updated doc before each meeting.
  • Build for hand-off — the team should run this without you over time.
In This Issue

Table of Contents.

The Cover introduced three layers — Instant Clarity (the 90-Day Revenue Execution Sprint), Bloom Growth Operating System (the framework underneath), and Constant Clarity (continued team alignment and accountability). This table of contents is the navigational view: the tabs, organized by layer. Skip anywhere — or return to the Cover any time via the leftmost tab.

Where we are

Completeness map · moved.

The Completeness Map has moved to the Overview tab, where it sits paired with You Are Here — the two views work together as the “where we are” section. Open Overview →

Department · The Revenue Meeting

The Revenue Meeting.

The bi-weekly working list — the engine of the Bloom Weekly Meeting. O&Os are the centerpiece of the meeting agenda (see The Operating System · Section 1 for the full Bloom Weekly Meeting structure and the 3D process). This tab is where the working list lives between meetings: every entry moves through Discover → Discuss → Decide, then either resolves into a To-do, becomes a solved decision archived in the Appendix, or stays open to be re-prioritized. The four sections below organize the meeting's working surfaces: the live agenda, the active pipeline, the to-do's, and the O&O list sorted by status.

Section 1
What we work through, in order

Meeting Agenda.

The 90-minute Bloom Weekly cadence. Check-in, KPIs, Deals, To-do's, O&O list with the 3D process, Wrap-up. Deals are walked through the pipeline table in Section 4 — each deal links to its stage in The Playbook for the live conversation. This is the operational instance of The Operating System · Section 1.

Vol. 3 · No. 2· June 10, 2026
The Meeting
90-minute Revenue Leadership cadence.
Bi-weekly · Tuesday · Bloom L10
90 min total · 5 min flex
5 min
Check-inPersonal & professional best
5 min
Discuss KPIsPipeline math · activity vs target
15 min
Discuss DealsWalk pipeline table · deal-by-deal · click into stages
5 min
To-Do ReviewDone or Not Done
55 min
O&O List · 3D processDefine → Discuss → Decide · institutional record
5 min
Wrap-UpNew to-dos · meeting rating

The agenda is the structure. The next section is the live deal pipeline — the 15-minute “Discuss Deals” block runs against this view.

Section 2
Where every active deal sits today

The Pipeline.

A stage-grouped view of every deal currently in play, as Mike walked through it on June 10, 2026. Bridges until HubSpot pipeline dashboards go live. Updated at every leadership meeting — Mike narrates each deal by stage, Dan updates this section before the next issue ships. Each stage maps to the Master Flow in The Playbook tab.

Snapshot
June 10, 2026 · 9 active deals across 5 stages
Pipeline at a glance · in-meeting matrix

Active deals this cycle.

Compact pipeline matrix — one column per deal, one row per signal. Use in-meeting to scan status. Click any deal header to jump to that deal’s stage in The Playbook. Click Issues row links to jump to the matching O&O. The deeper deal-by-deal narrative sits below this table.

Signal UTS / Fitzmark Bruce Parsons · in diligence WTS Canada LOI redlined · investor mtg Freight Logistics Wally referral · 3 buyers Challenger DFW Loan structure rejected FastExact Bay Area · Landstar route Map Parcel San Diego · 6.5x ask Extreme Trucking Valuation forming Paystar Contract-based · 7 customers Jetliner Alkaos Travis Nelson · portal
Stage 09 · Diligence 08 · LOI 08 · LOI 08 · LOI 07 · Connected 07 · Connected 04 · Evaluation 03 · Education 03 · Portal
Status Active Active Active On Hold Active Watching Watching Watching Active (portal)
Last activity Data room catch-up call. Initial checklist round complete. LOI redlined & sent. Buyer investor mtg Thursday. ITF defending offer. Mike sent coaching email. Owner consulted outsider, pulled. Loan structure off. Alan Lund passed. Mike opened Landstar · SIM sent. Owner returned at 6.5x ask. Friendly competitor poor offer. Updated financials in. Normalization conversation with CFO. Mike reaching out repeatedly. Awaiting reply. Engagement signed. Files received. Asking about acquisition fees.
Next step Continue diligence coordination. Watch Owens Corning concentration. Buyer response by Friday on redlines. Push 3 buyers for valuations to compete ITF offer. Wait for buyer to come with 100% cash structure. Landstar agent matching · confirm interest. Hold · reassess when seller expectation realigns. Land the revised valuation · confirm seller still wants to go. Continue outreach · possible new buyer match. Watch for shift from portal subscriber to active seller.
Watch / blocker O&O #38 Owens Corning concentration Small + Canadian profile Seller losing patience Likely restart late 2026 Sub-$5M deal · small profile Seller expectation gap Revised valuation lower than first read Customer concentration (7) No money received yet on portal sub
Owner Mike · Ron + Jay (data room) Mike Mike · Wally referral source Mike Mike Mike Mike · CFO contact Mike Mike
Deep read Open UTS → Open WTS → Open FL → Open Challenger → Open FastExact → Open Map → Open Extreme → Open Paystar → Open Jetliner →

Each column links to the matching Stage spread in The Playbook so the team can jump from a deal in this meeting straight to the play for its stage. Watch/blocker row links to active O&Os. Deeper deal-by-deal narrative follows below — the table is for scanning; the narrative is for working through one deal in depth.

Stage 09
Diligence
1 deal · closing target before fall busy season
Bruce Parsons · UTS / Fitzmark
Active
In due diligence with Fitzmark as buyer. Data room open. Initial round of checklist items just completed. Mike is running the diligence coordination; Ron and Jay took over data room management on this deal. Buyer forced SharePoint as the data room platform. Open watch item: Owens Corning concentration risk (see O&O #38) — Bruce’s largest account is Owens Corning, and Fitzmark also services Owens Corning at a different region/plant. Fitzmark says won’t affect valuation. Worth documenting proactively in the data room. Stage 09 walk-through on June 10 generated 4 new operating principles — see The Playbook · Stage 09 · Operating Principles.
Stage 08
LOI
3 deals · mix of advancing, stalled, and on hold
WTS · Western Canada
Active
LOI redlined with additional changes. Mike went through the redlines verbally with Agent AI (the prospective buyer’s rep) and forwarded the redline LOI. Buyer has an investor meeting Thursday and committed to a response by Friday on whether the redlines are acceptable. Buyer estimates 45–60 days for due diligence on this kind of deal. Small Canadian deal — tough profile but moving.
Freight Logistics · (Wally referral)
Active
LOI on the table from ITF (St. Louis) but the offer is under market. Mike sent a coaching email yesterday; ITF replied during the June 10 meeting defending their offer as reasonable. Two other buyers (Dynamic Connections + one more) in conversation — pushing all three for evaluation responses. Seller is getting impatient, doesn’t want to blow up the current ITF LOI but knows the offer is light. Goal: get competing valuations on the table fast.
Challenger Freight · Dallas / DFW
On Hold
Current LOI altered terms to ask for $1M of cash-at-close in the form of a loan at attractive interest. Three owners on the seller side agreed initially; then one owner (who owns majority of sales) consulted with an outside person who knew nothing about the deal and was told the structure was wrong. That owner pulled. Deal is now on hold until the buyer can come up with 100% cash at close without the loan structure. Realistic restart: closer to end of year.
Stage 07
Connected
2 deals · new buyer introductions in flight
FastExact · Bay Area, CA
Active
Under $5M revenue, very profitable. Alan Lund passed yesterday on the opportunity. Mike set up a new buyer introduction the same day: Landstar — ~$5B agent organization, with agents as large as $500M. Landstar’s acquisition rep will match FastExact with specific agents in their system focused on concert venues and trade show freight. SIM sent to Landstar. Strong fit because Landstar can route the small-deal profile to the right internal agent. Could become a recurring pipeline for similar small-deal opportunities.
Map Parcel Express · San Diego
Watching
Mike originally met with owner and parents (also owners), gave a presentation, told them market multiple was ~5x for a current EV around $20M. Owner came back saying he needs a 6.5x multiple to make the sale worthwhile — unrealistic for current market. Friendly competitor returned a poor offer. Deal is iffy until the seller’s expectations realign with the market.
Stage 04
Evaluation
1 deal · valuation forming
Extreme Trucking
Watching
Asset-based. Seller initially passed on providing key inputs (employee data, equipment files, normalized expenses) so the rough draft valuation relied heavily on assumptions — including a $500K normalized expense estimate (typical or even light for asset companies). After significant delay, seller agreed to go to market and provide the missing data. Mike got updated financials this week. Yesterday's call with CFO clarified the normalization method. Concern surfacing: the assumptions that bolstered the initial valuation are not coming through — very few actual normalized expenses, equipment files still pending. Initial valuation likely lower than first read. Open question: will the seller still want to go to market once the revised number is on the table?
Stage 03
Education / Portal
2 deals · long-term plays + Customer Portal subscribers
Paystar
Watching
Contract-based $30M brokerage with only seven customers total. Was originally taken to multiple buyers; all passed at near-market valuation because of the customer concentration. Team explored buying smaller companies to increase shipper count and acquired UTS as a potential merger target — gyrations didn't ultimately work for Paystar. New buyer interested specifically in contract-based deals. Mike has reached out to Paystar several times to confirm willingness to go back to market. Awaiting response.
Travis Nelson · Jetliner Alkaos
Active (Portal)
Came from a TIA event. Initial acquisition conversation surfaced that Travis was not ready. Signed the engagement agreement for the Customer Portal subscription (monthly fee). Files received and processed this past week. Identified items missing from the original checklist; followed up by email. Recent call signal: Travis was asking about the acquisition agreement and what Next Mile’s fees are. Possibly starting to lean toward going to market. Note: no money received yet on the portal subscription. This deal anchors the open question in O&O #44 — what stage are Customer Portal subscribers actually in?
The honest read. Mike's framing on June 10: “Got a lot of stuff going on, but some tough deals.” WTS is tough because it’s small and Canadian. FastExact is sub-$5M and California. Map Parcel and Extreme Trucking both have seller-expectation gaps. The product of the market the last several years — companies that agreed to go to market in 2025 knew they were on the weak side. UTS is the strong-quality deal that bodes well for the closing rhythm going forward. The hope: as the new networking and post-TIA cycle produces more deals, more of them look like UTS than Map Parcel.

After the deals: what owners committed to last meeting and whether it got done.

Section 3
Outputs of the last 3D session

To-do's.

Owned commitments from the last meeting. Done or Not Done. Per Bloom, the goal is 90% completion every 7 days. To-do's are the most sacred promises the leadership team makes between meetings.

Next Actions · May 12, 2026

Open by owner.

Committed actions assigned by owner. Weekly check-in. Closed items move to the Decisions Log; the rolling count tracks velocity. Items below reflect commitments from the May 12 leadership call and prior sessions still open.

Dan Klein
6 Open · 1 Done
Schedule stage-to-system mapping call DONE
Mike + Ciara + Dan. Mapping call scheduled for the Spoke Phase 2 Build kickoff (week of May 4). Stages decided in that session, then Ciara builds them in HubSpot.
Coordinate Dropbox location for living playbook
Per June 10 meeting: Wally asked the doc live in Dropbox (read-only) so the team always has the latest. Jay's input needed on Dropbox protocol and folder location before placement. Once Jay confirms structure, upload current HTML and PDF to agreed folder; replace on each new issue.
Email Jay HubSpot Sales Pro upgrade link · collect signature
Pair to Jay's open to-do (Sign HubSpot Sales Pro quote). Mike + Wally need Pro features (sequences, lead board, automation) unlocked before Sierra can finalize Phase 2. Send the upgrade link to Jay and confirm receipt.
Define HubSpot emergency support process with Sierra
Per Wally's June 10 ask: Mike and Wally need a way to reach Sierra outside the regular kickoff and training cadence when something blocks a deal. Same-day response, not five-day wait. Define the channel (email + text), the trigger (Mike or Wally judgment), and the expected turnaround. Document and share with Mike + Wally.
Schedule HubSpot kick-off overview with Mike + Sierra
First step in the HubSpot ramp Mike committed to on June 10. Sierra walks Mike + Wally through what's been built and what's coming. Then Sierra schedules individual training (Mike data download session, Wally workflow training). Loop in Wally on the kick-off invitation but he is okay with Mike going first.
Schedule tech sync with Jay & Sierra re: automated recording
June 10 meeting surfaced this as a blocker: Mike and Wally need recordings to flow automatically into HubSpot (the deal/contact record) without manual file uploads. Sync with Jay (tech lead) and Sierra (HubSpot configuration). Decide on a tool (Read.ai, Fathom, Zoom native), agree on the routing rule (transcript lands on the right contact / deal record), then share the setup steps with Mike and Wally.
Schedule 1:1 walkthrough with Mike re: the living playbook
Mike asked on June 10 (after John left) for a personal walk-through of this document — the same one Wally received before the meeting. Mike said he learns by doing. Schedule within the next two weeks. Walk through every tab, focus on Sellers and the Stage 09 additions Mike provided during this meeting.
John Knicely
1 Open · 2 Done
Compile & share both agreements
Referral agreement + engagement agreement drafts to Mike + Wally. Reassigned from Dan to John per Vol. 1 No. 1 review. Must be finalized before COI introductions begin.
Exit Readiness Library · next recording
Recording scheduled May 13 at 11 CT, 30–45 min. Topic: "Top ways deals get blown up" or "Seller fatigue" (Mike's call). Mike + Wally on the recording before Mike leaves for Italy May 14.
Next exit-readiness piece · topic ideas + recording schedule
Committed on June 10: send Mike + Wally a list of topic ideas for the next exit-readiness library entry (the May 26 piece “The Top Ways T&L M&A Deals Get Blown Up” is the model). Mike or Wally picks the next topic. John schedules a 30-minute recording to capture Mike + Wally's voice on it. John writes; piece feeds the nurture sequence as the next campaign asset.
Ciara Brewer
0 Open · 2 Done
HubSpot Sales Hub stand-up · per May 26 quote DONE
Foundation layer shipped Jun 11: Lead Status stages, Deal Pipeline, custom contact properties, record layouts, bounce cleanup. Now mid-segmentation (Seller / COI / Buyer tagging across existing contacts).
HubSpot email-tracking default · Outlook DONE
Email tracking configured across user accounts. Outreach and replies now visible on the contact record.
Jay
1 Open · 0 Done
Sign HubSpot Sales Pro quote
Sales Pro upgrade is the gate for sequences, the visual lead board, and the automation layer. Foundation layer is in (June 11); Pro features unlock the next phase. Jay approves vendor + tech proposals; sign-off here unblocks Ciara to finalize the upgrade and load active deals into the pipeline.
Mike Bloss
1 Open · 0 Done
Export & send email templates to Dan + Sierra
From June 10: Dan was not able to access Mike's email templates through Mike's Windows system / Outlook account. Method Mike used previously and will use again: run a test email of each template to himself (so any attachments come through correctly), then forward each test email to Dan and Sierra. Recipient list: Dan + sierra@spokemarketing.com. Sierra loads them into HubSpot. Without these, the HubSpot stand-up is incomplete on Mike's side.
Mike + Wally
5 Open
Set 2026 1-year goal
3-year target is 12 deals/$10M+. 2026 cascade is open. Closed-deal target, revenue target, channel-mix split. Needed before Growth Plan 1-Year card finalizes.
Confirm Q2 goals
Provisional Q2 goals listed in Overview · North Star. Replace with the actual leadership goals from the next Tuesday working session.
Post-TIA pipeline triage
Booth visitors, scheduled follow-ups, Tier 1/2 COI conversations from Apr 15–16. Tag every contact in HubSpot, advance into the right stage, surface immediate action items.
Review call summaries · send corrections to Dan
Five call summaries live in Records · Section C: Bruce Parsons / UTS, Chad / Freight Logistics, Kevin / Tenstreet, Evan / Armstrong, Travis / Xtreme. Mike + Wally review each one and flag what's wrong, missing, or framed inaccurately. Wally already caught one name correction (Bruce’s surname) on June 10. Expect more corrections like that — the summaries were AI-generated from call transcripts. Send corrections to Dan; he updates the doc.
Wally Brauer
1 Open
Walk through the interactive plan with Dan DONE
Once Dan shares the link to this document, schedule a working call. Wally reviews page by page on screen-share, records questions live, decides which items need follow-up. Mike walks through separately when back from Italy.
Jay Roberts
2 Open
Set up Claude team account DONE
5 seats: Mike, Wally, Jay, Ron, Dan. Research the team-plan pricing tier ($20–$125/seat range). Jay charges to the business card. Mixed-tier seats acceptable if heavier users (Dan, Mike) need the higher cap. Per May 12 call.
Walk Wally through the Google Drive project folder
Wally asked for visibility into where Dan and John save shared assets. Quick screen-share to show the folder structure and key files. So Wally can self-serve reference material between meetings.
Jay / Ciara
1 Open · 0 Done
Hook Claude up to HubSpot
Claude Team account is set up. Next step: connect Claude to HubSpot so the playbook can pull live deal data, contact records, and pipeline status without manual screenshots. Jay drives the integration approval and technical scope. Ciara configures HubSpot side (API keys, permissions, what data Claude can read).
Moved to Obstacles & Opportunities
2 Open
Gifting protocol — ownership & spec → see O&O
Concept agreed: handwritten thank-you note + small personalized gift per COI introduction. Discussion needed: who owns the protocol, who funds it, what the spec is. Tracked as an Obstacle & Opportunity for the next leadership working session.
Operating System department needs a working session → see O&O
The Operating System tab is scaffolding until 1-year goals are locked and HubSpot pipeline data goes live. Working session with Mike + Wally to land goals, math, and KPIs. Tracked as an Obstacle & Opportunity.
"Honor what exists. Make instinct teachable."

To-do’s are the outputs. The O&O list is the input — what gets discovered, discussed, and decided next.

Section 4
The working list, by status

The O&O list.

Thirty-seven items in active circulation. Sorted by status: Define (earliest scope), Discuss (active leadership conversation), In Approval (close to decision), Solved (institutional record). Sticky sub-TOC inside this section lets you jump between status groups.

Obstacles & Opportunities

By topic.

Thirty-six entries across seven topical sections. Each entry is something the bi-weekly leadership meeting either decides, discusses, or names. Status shown as a small badge (Define · Discuss · In Approval · Solved). Cross-references between entries appear in-line. Pre-existing solved decisions roll up into the Appendix as their detailed write-ups; the bottom section here keeps the headline-level record visible in the working list.

Section A
Items to scope · earliest stage

Define.

The longest list. 18 items the leadership team has named but not yet brought to a structured Discuss conversation. Most are 3D-process inputs awaiting the right Tuesday. Define-status items typically need: a working title that everyone agrees on, a one-sentence problem statement, and an owner. Once those three exist, the item is ready to move to Discuss.

44
Opportunity
Customer Portal sellers · which stage are they in?
Surfaced June 10 during Mike's walk-through of how to use the playbook live. Mike was previewing tomorrow's meeting with Windmill / West Michigan — a current Customer Portal subscriber — and the team realized the playbook does not have a clean answer to: what stage is a Customer Portal seller in? Mike’s instinct: generally Preparation, because the portal is prepping the seller for selling (TMS data being uploaded monthly, KPI clean-up, multiple-tracking). Wally’s read: could be Engagement or Education — Windmill is not ready to sell now and won’t be in the near future, but finds Mike’s spreadsheets useful for ongoing operating insight. The Master Flow has the Portal documented as a branch off Stage 04 Evaluation (off-ramp for the “not yet, not no” sellers), but the stage placement of an active portal subscriber is genuinely unclear.
Define(1) Mike + Wally working session: walk through Windmill / West Michigan + the other current portal subscribers and place each one in a stage. (2) Decide whether Customer Portal subscribers occupy a stage at all in the standard journey, or whether the Portal is a parallel track with its own status that intersects the main flow at specific stages (Stage 04 Evaluation entry / Stage 05 Preparation re-entry). (3) Update the Master Flow visualization in The Playbook tab to reflect the decision. (4) Update HubSpot pipeline configuration to match (Ciara to confirm what's buildable).
○ Define
39
Opportunity
Exit Piece nurture · "The Top Ways Transportation M&A Deals Get Blown Up"
New long-form piece published May 26, 2026 (link in Records · Section B). Anchored in Mike's process: financial variances under a multiple, TMS data quality, concentration drift, the seller's own state of mind. Built around the four places deals consistently break down, with a real case study that closed because the gross profit concentration risk was surfaced from day one. Includes a direct Wally quote on seller emotions ("They are going to have emotions. For us to tell them they're not is just not truthful."). This is the strongest piece of nurture content the firm has produced and should be the spine of the next campaign cycle.
Define(1) Confirm distribution plan: who gets it, on what cadence, through what channel. (2) Decide on the campaign structure: standalone send, drip series, or anchor of a broader content sequence. (3) Identify the audience cuts — engaged-not-ready sellers, COIs (attorneys/insurance/finance), cold targeted list. (4) Schedule the next piece in the library (seller fatigue, per the article's own teaser). (5) Sierra/Ciara: get this loaded as a sequence asset in HubSpot once the foundation layer is in.
○ Define
40
Obstacle
HubSpot foundation in by Wednesday · segmentation blocked · decisions needed
Ciara confirmed June 8 that the foundation layer ships by Wednesday June 11: Lead Status stages configured, Deal Pipeline built, custom contact properties live, record layouts set up for both users, bounce cleanup done. Blocked on database segmentation — tagging Seller/COI/Buyer across existing contacts. Company-level field already exists ("Buyer, Seller, or General") with 341 companies marked; question is whether this needs to live on the contact record too, and which contacts get the COI flag. Mike can be operational in HubSpot within one week of SOW signature + Pro upgrade confirmation. Full property architecture and Ciara's status email live in Records · Section F · CRM Build.
Define(1) Sign the SOW and provide billing address for the deposit. (2) Confirm the HubSpot Sales Pro upgrade quote — sequences, visual lead board, and automation layer all depend on it. (3) Schedule Al's pull from Mike's Access file so active deals can be loaded into the pipeline before Wednesday. (4) Open a window for Mike to do the data download session with Ciara. (5) Decide whether Seller/COI/Buyer flag goes on Company, Contact, or both — and define which existing contacts get COI tagging. (6) Auto-pipe call notes into HubSpot — Ciara to set up automation so meeting transcripts and call recordings flow into the relevant contact/deal record without manual upload.
○ Define
41
Opportunity
How we use this document · making it real for the sales side
This document exists to be marked up, not admired. The Sellers section in particular is where Mike’s and Wally’s fingerprints need to be — the mindset content, the scripts, what we say at each stage. Right now a lot of that content is what John and Dan think is true based on the calls we’ve reviewed. But the operators on the front lines need to react to what’s wrong. New “How to Use This Document” page added to the Cover tab — three owner blocks (Mike/Wally/Jay shared, Ron, Dan) with explicit instructions on what each person does between meetings, in meetings, and (for the sales team) how to use the buyer’s journey matrix as a credibility piece in COI conversations.
Define(1) Walk through the new "How to Use" page — confirm each owner agrees with their role. (2) Commit to the cadence: Mike + Wally mark up the Sellers section between meetings, ship reactions to Dan before the next issue. (3) Decide whether the doc gets emailed to the broader sales team yet, or stays at the leadership level until stable. (4) Confirm the recording workflow that feeds the Sellers content (see O&O #42).
○ Define
03
Opportunity
Mike + Wally Pipeline Update · Visibility Until HubSpot Cutover
Until the HubSpot Sales Hub cutover lands (per Spoke Marketing May 26 quote, Mike's cutover end of Week 2 ≈ Jun 8 with full system live Jun 30), the team has no shared view into what's actually moving in Mike's homegrown CRM. The 1 active $26M deal lives there. The post-TIA conversations (12 sellers, 6 buyers) live in Mike's head and notes. We need a structured Tuesday update from Mike + Wally: active deals by stage, new conversations from TIA, stage transitions since last meeting, blockers or near-term decisions. This is the bridge to the live HubSpot dashboard.
DefineAgree on a simple weekly update format (5-min recap at top of Tuesday meeting): active deals · what moved · what's stuck · what Mike needs. Capture in this document going forward. Sunsets when HubSpot dashboards go live.
○ Define
04
Opportunity
Portal & AI · Strategy Discussion
The Portal (now inside Sellers) has two populations (Population A: Engaged Not Ready sellers off-ramping from Stage 04 · Population B: paid subscribers using it as an operating-view product) currently scoped for Phase 3. Open strategic question: how does AI accelerate the Portal? Candidates: AI-powered Exit Readiness Scorecard (richer diagnostic than the static 3-minute version), AI-summarized library content for Population B subscribers, AI-driven comparables matching, automated valuation indicators, AI-assisted CIM drafting for Active Process sellers. The Black Belt TC engine already contains 430+ financial charts and proprietary methodologies — the question is which AI layer compounds that asset vs. dilutes it.
DefineMike + Dan working session: scope what AI does in the Portal (Population A and Population B) before Phase 3 build begins. Identify IP-protection boundaries (per Tier 5 TMS/tech vendor signal). Decide what's in v1 vs. v2 of the Portal. May 26 refinement (Ron + Jay): the underlying engine (Mike's data-manipulation panel, his “cockpit”) stays — he needs the dense control-surface for live presentations. The opportunity is a wrapper: a cleaner front-end for subscription customers (Population B), and an AI interface that surfaces what the data means so non-Mike users can interpret it. Don’t replace the engine; wrap it.
○ Define
05
Opportunity
Buyers Database · Foundation
Per the Hero's Journey doc, Next Mile has a database of 300+ strategic transportation buyers with relationships built over decades. Currently lives in Mike's homegrown system (and Mike's head). 6 new buyers were captured at TIA (per Spoke SOW post-TIA bundle), imported as plain contacts pending Phase 3. Open questions: how do we get the full 300+ database into HubSpot? How do we segment (strategic vs. financial · mode preference · size band · geography)? How do we keep it fresh as buyer mandates shift? This is the foundation work for Buyers, which is scoped for Phase 3.
DefineMike + Ciara + Dan working session: scope buyer database migration into HubSpot (separate property structure from Sellers · matching criteria · refresh cadence). Sequence relative to Phase 3 launch of Buyer campaigns.
○ Define
06
Obstacle
Gifting Protocol · COI Introductions
Concept agreed: handwritten thank-you note + small personalized gift for every COI introduction (idea: custom bourbon glasses with the note "Can't wait to toast with you when they sign"). Specific item, budget, and fulfillment owner all TBD.
DefinePick the item. Set the budget. Assign the owner. Define before the first COI referral comes in.
○ Define
07
Obstacle
2026 1-Year Goal Cascade
3-year target is set (12 deals · $10M+ · ~$40M avg). 2026 milestone — closed-deal target, revenue target, channel split — is open. Without it, the Math section can't close and the bi-weekly scoreboard reads TBD.
DefineMike + Wally working session to set 2026 cascade. Reconcile to current pipeline ($26M · 1 active deal).
○ Define
08
Obstacle
Math Inconsistency · LOI Cadence vs. 12-Deal Goal
Deck targets 2 LOIs/quarter (8/yr) at 90% close — produces ~7 closes/yr, not 12. Either LOI cadence target needs to roughly double, close-rate assumption needs tightening, or 12 deals is a 3-year endpoint that ramps from a smaller 2026 number.
DefineResolve in next leadership working session. Tied to Obstacle 07 (1-year goal cascade).
○ Define
09
Opportunity
AI Tooling · Claude team account selection
Per May 12 call, the team agreed to standardize on Anthropic's Claude for an internal AI assist. Five seats discussed: Mike, Wally, Jay, Ron, Dan. Open questions on plan tier ($20–$125/seat range) and whether to mix tiers (heavier users like Dan + Mike on higher cap, others on entry level). Wally on the call: "I mean, we might as well be on the same one, Jay, if you're on Claude, just to have Mike do the same thing, we can always switch later." Jay tasked with research and proposal.
DefineJay researches team-plan pricing and proposes seat configuration to Mike. Once approved, Jay charges to the business card and provisions seats. Dan + John can support onboarding (they already run a team Claude account).
○ Define
19
Opportunity
Diagnostic Posture · Name the Brand Asset
The single most validated finding across the calibration set. Mike's posture — push back on the owner's optimistic narrative, don't tell them what they want to hear — is what sellers consistently name as the trust unlock. Doug Hazen (2022): "He never told me what I wanted to hear. He just told me how it was." Travis / Xtreme (Apr 3, 2026, call min 25:03): "You responded well, every owner says that and thinks the market's going to save them. But we're actually doing some hard stuff." Same posture. Two sellers. Four years apart. Same response. Currently implicit (lives in the Doug Hazen quote and Mike's behavior). Should be named explicitly as the central operating principle of the firm.
DefineName the principle. Working title: "Diagnostic Posture." Land it in Sellers · Overview or as a cross-cutting brand principle. Capture canonical articulation. See Appendix · Call Summaries · Travis/Xtreme + Bruce/UTS.
○ Define
20
Opportunity
Seller Archetype Framework · Add the "Experienced Acquirer" Dimension
Sellers currently tiers sellers by engagement state (1A/1B/1C/1D). It does not distinguish sellers by acquisition experience — which the calibration data shows is a critical pacing dimension. Chad / Freight Logistics: zero prior M&A. Bruce / UTS: 3 transactions + 1 acqhire as buyer. Travis / Xtreme: 6 acquisitions as buyer. These three operate at fundamentally different speeds in a Stage 04 conversation. Treating Travis like Chad would have lost credibility in the first 10 minutes; Mike correctly didn't. Recommendation: add an intake question — "How many companies have you acquired or sold previously?" — and route accordingly. Experienced-acquirer sellers get a fast-track Stage 04 variant with less pedagogical framing.
DefineAdd intake question to Stage 02 / Stage 04 discovery framework. Draft fast-track Stage 04 variant. Decide: separate tier (1A-E) or overlay dimension on existing 1A/1B/1C/1D? See Appendix · Seller Matrix.
○ Define
21
Opportunity
Seller Motivation Archetypes · Document the Drivers
The playbook frames "why are you selling?" as the diagnostic question. It is the right question — but the answers cluster into archetypes that warrant different content tracks. Bruce / UTS: Culture-first founder — "I want my people home with their families." Wants to protect what he built. Chad / Freight Logistics: Lifestyle / baton-handoff — "Looking to hand the baton off." 60 years old, work-life balance. Travis / Xtreme: Identity / next-chapter — "I'm 41. I need to have some sort of purpose." Not retirement; strategic. Two canonical archetypes implied by the playbook (Retirement, Health/Forced) were not seen in the calibration set. Documenting motivation archetypes lets the Exit Readiness Library tag content by archetype rather than topic.
DefineConfirm/refine archetype list (Legacy/Culture · Lifestyle/Succession · Identity/Next-chapter · Retirement · Health/Forced). Map Exit Readiness Library content to archetypes. Identify gaps. See Appendix · Seller Matrix.
○ Define
22
Obstacle
Household Alignment · Missing Stage 04 Sub-Step
Travis / Xtreme on Apr 3, 2026 (call min 43:30): "I haven't told my wife or anything." This is the emotional gate that follows the valuation strike and precedes the contract. Wally's coaching response (43:46–44:15) was operationally beautiful — "You're only as good as your wife, so make sure she knows that" — but it was improvised, not scripted. The Stage 04 spread currently does not include a Household Alignment sub-step. Without one, calls end open-ended with no defined next interaction. Wally's improvised script should be captured as the canonical posture for this moment.
DefineAdd "Household Alignment" sub-step to Stage 04 in the Pipeline. Capture Wally's coaching language as canonical script. Decide whether framing presumes spouse/partner (avoid presumption for solo founders). See Appendix · Call Summary · Travis/Xtreme.
○ Define
23
Obstacle
Close-the-Loop Calendar Discipline · Cross-Cutting
Every Stage 04 seller call AND every Stage 02+ COI call in the calibration set ended open-ended. Travis: "Take a moment over the weekend." Kevin: "As we continue to communicate." Evan: ended with Mike trying to call via cell after Zoom failed. Chad: closer to defined next step but no specific time calendared. No call closed with a specific next-interaction calendar commitment. This is a discipline gap, not a script gap — the playbook should establish the rule.
DefineMake "defined next interaction" a non-negotiable close pattern across all Stage 02+ conversations (Sellers, COIs, Buyers). Pattern: "Let's calendar 20 minutes [day] at [time] to [specific topic]." No open-ended "reach out if you have questions." Cross-reference Pipeline standard.
○ Define
24
Opportunity
Sellers · Brand Assets · Three Pieces Needed
The calibration surfaced three Sellers brand asset gaps. (a) Mid-Length Operator Pitch (2–3 min): Mike's full bio ran 6 min on Tenstreet, ~3 min on Armstrong. The playbook has the 30-Second Conversation and the full biography — nothing in between. (b) Wally Exit Story · Canonical Version: Already operating as the peer-credibility unlock (trust-builder on Call-02/Chad; structural positioning lever on Call-06/Travis). Needs documentation in three formats: full (~7 min), structural fragment (~90 sec), single-sentence positioning. (c) Live Valuation Revision Story (anonymized): Call-06 sequence at min 24:30 — Mike struck $20.5M EV, Travis surfaced Q1 lift, Mike re-ran math live on screen in 90 sec, revised EV to $27.7M. Belongs as anonymized case-study material.
DefineScope the three assets. Owners: Mike + Wally (pitches) · Natalie Nicole / John (case study format). Sequence relative to other content production. See Appendix · Brand Asset Inventory.
○ Define
29
Obstacle
COI Directional Tracking · Bidirectional Relationships in HubSpot
Both COI calls revealed COIs that are also buyers (or represent buyers). Kevin / Tenstreet: Tenstreet is an acquirer (~2 deals/year); Kevin is also referral source. Evan / Armstrong: 4 active buy-side deals representing acquirers AND ~4,000 company profiles, knows sellers. Current playbook treats COIs as one-way. HubSpot needs to handle: same person, two relationships (COI role + Buyer Database role), two attribution frameworks, two economics tracks. Without separate tracking, attribution gets scrambled when a Tenstreet-routed seller closes — was that a COI referral or a buyer database match?
DefineWorking session: Mike + Ciara. Scope HubSpot config for multi-role contacts. Naming convention. Sequence relative to Buyers Database migration (O&O #5). See Appendix · COI Matrix.
○ Define
31
Opportunity
Buyer Calibration · Phase 2 Sales Call Analysis
The Phase 1 calibration set has 3 seller calls + 2 COI calls. Zero buyer calls. Sellers play and COIs play now have living voice-of-prospect material. Buyers play has nothing. The 300-buyer database is the firm's competitive moat, yet there's no calibrated understanding of how buyers actually talk, what they object to, what they need from a SIM, or how they decide. Phase 2 should include 3–5 buyer calls. Candidates: Steve Frankhill / Dynamic Connections (referenced on Call-02); buyers from the eight who met the current Denver seller at TIA; the 12–14 buyers who looked at Wally's Freight Solutions deal. Different risk profile than seller / COI calls — buyer conversations are confidential and high-stakes. Different recording norms may be needed.
DefineDecide whether Phase 2 calibration is scoped now or deferred. Identify 3–5 target calls. Confirm recording norms (buyer consent, NDA-adjacent protocols). Sequence with Buyers Database migration (O&O #5) and Buyers · Foundation work.
○ Define

Define is the queue. Discuss is the working session. The next section is where the leadership team's active conversation lives.

Section B
Active leadership conversation

Discuss.

16 items moving through the 3D process — the first three are clustered at the top for the Jay conversation. This is where the bi-weekly meeting spends most of its O&O time. Each item has been scoped enough to talk about; the team is now exchanging perspectives, surfacing root cause, identifying decision owners. The output of Discuss is either a recorded decision (moves to In Approval → Solved) or a refinement back to Define if scope was wrong. One item below is currently on-hold — paused but not closed (the Accountability Matrix, deferred until role definitions land).

For the Jay conversation

Three Discuss items for Jay.

These are the live operational items that came out of the June 10 meeting and the June 10 invoice exchange with Jay. Each one has a clear context elsewhere in the doc — pre-read links below. Sending Jay an email ahead of the call to ground the conversation; this cluster is where the live Discuss happens.

Marketing recap (Jay’s ask)
Records · Appendix G · Marketing Partners →
Why marketing first, then CRM
The Stack · Architecture →
Immediate sequence (what's next)
Overview · You Are Here · Phase 2 →
Call flow / why recording matters
The Stack · Call Flow →
42
Obstacle
Call recording logistics · where, how, who shares
The doc only sharpens if the team is sharing call recordings. Today the workflow is informal — sometimes recordings reach Dan, sometimes they don’t, sometimes only the transcript does. Need a standing logistics agreement so this becomes habit, not an ask. Likely tools in play: Read.ai, Fathom, Zoom native recording, or HubSpot’s built-in once it’s configured. Need one source of truth, automatic sharing, and a place all recordings/transcripts land.
Discuss(1) Pick a primary recording tool for the team — one tool, not three. (2) Decide where recordings/transcripts land (HubSpot deal/contact record, shared drive, both). (3) Agree on the rule: every external sales call gets recorded, full stop — with a standing disclosure at the top of the call. (4) Confirm Ciara’s scope to auto-pipe transcripts into HubSpot (see O&O #40, item 6). (5) Decide who’s accountable for the recording happening on each call (the host, probably). Resolution path (added Jun 11): 30-minute tech sync this week — Jay + Sierra + Dan. Sierra confirms HubSpot auto-routing config. Decide tool. Dan drafts a layman’s setup guide for Mike + Wally afterward so they don’t have to think about it. This is the upstream input that lets Claude close the loop — see The Stack · Call Flow.
◐ Discuss
43
Obstacle
Doc hosting & version control · Wally’s HTML access as immediate symptom
The broader question: the doc is sent as a fresh HTML file every two weeks. The team has to remember which version is the latest. Wally on June 10: "is it kind of like Dropbox that as you guys make changes to it, it’ll update on our system, or do you have to send us an updated copy?" Today the answer is “new copy each time” — not scalable. Two paths: (A) Dropbox hosting (read-only folder, single location, works now but Dropbox’s HTML preview doesn’t render the doc properly — viewers download + open); (B) stable URL on a domain or GitHub Pages — team bookmarks one link, refreshes for latest. Dropbox is the easy short-term answer per Wally’s ask; stable URL is the better long-term answer. The immediate symptom is Wally’s file-association problem: double-clicking a .html file on his machine doesn’t default to a browser. Workaround steps: (a) Save the .html file to Downloads or desktop — don’t open from email. (b) Right-click the file. (c) Choose “Open with” then pick Chrome, Edge, or Firefox. (d) Optionally check “Always use this app.” If that fails, drag the file directly onto an open browser window.
Discuss(1) Immediate fix for Wally: walk through the Open With steps above in real time on next call. (2) Confirm the PDF version stays as his backup for marking up by hand. (3) Strategic decision with Jay: Dropbox or stable URL for hosting the live doc — Dropbox now (per Wally’s June 10 ask), revisit stable URL once Phase 2 of HubSpot is stable. (4) Define the Dropbox folder structure with Jay — see O&O #45 (file management). (5) Confirm read-only access for Mike + Wally + Ron, read/write for Dan.
◐ Discuss
45
Obstacle
File management · Dropbox folder structure for the firm-level assets
No single agreed-on home for the firm-level marketing & operating files — call recordings, transcripts, brand assets, COI handouts, the bi-weekly playbook. Wally on June 10 asked that this doc live in Dropbox going forward, but the broader question is what Dropbox structure works across all firm-level files. The principle: deal-specific files belong on the deal record in HubSpot. Firm-level files (brand assets, decks, exit-readiness pieces, this playbook) belong in Dropbox. Need Jay to define the Dropbox structure since he’s the file-management owner per the How-to-Use card.
Discuss(1) Jay shares the existing Dropbox structure with Dan in a 15-minute working session. (2) Agree on three core folders: (a) Living Playbook (this doc, every issue), (b) Brand Assets (one-pagers, decks, exit-readiness pieces), (c) Call Recordings (transcripts auto-routed from the tool we pick in O&O #42). (3) Confirm read/write vs read-only access per role. (4) Cross-reference: deal-specific files go in HubSpot (not Dropbox); firm-level files go in Dropbox (not HubSpot). (5) Resolves the hosting question in O&O #43 in the short term.
◐ Discuss
10
Obstacle
Mike's CRM hold-out · transition timing + Italy gap
Mike continues running his homegrown CRM in parallel with HubSpot through Phase 2 Build. Per May 12 call: "Yeah, I have to stay on my CRM. There's no way I can keep up and I haven't got any training on CRM either." Mike will train when back from Italy (May 14–28). In the meantime, every deal Mike touches lives in his system, not HubSpot, so the leadership-level pipeline view depends on Mike as the human bridge. Three-week gap with Mike abroad. Workable in the near term; not sustainable at scale.
DiscussSet a target date for Mike's full HubSpot adoption (post-training, post-Italy). Define what "fully migrated" means: deals, contacts, activity logs, document library. Decide what stays in Mike's system permanently (proprietary analytics) vs. what moves (CRM activity).
◐ Discuss
11
Obstacle
Portal subscription pricing · version control on send
Per May 12 call: the team agreed a Portal pricing sheet (flat $5K or $500/month with 1-year minimum). Mike initially sent Vache the wrong version (flat $5K only), then corrected with the by-the-month option the next morning. Wally caught it on the call. Pattern signal: the canonical pricing doc exists somewhere but isn't the version Mike sends from. Low-stakes here (Vache is the first paid subscriber) but worth resolving before more Portal agreements go out.
DiscussConfirm where the canonical pricing sheet lives and that Mike sends from it. Optional follow-up: put the Portal pricing template in HubSpot's document library (Phase 2 Build scope) so every send pulls from one source.
◐ Discuss
12
Obstacle
Accountability Matrix · Deferred
Mike confirmed Mar 30: "That's a later thing, we don't have to deal with that." Deferred until the team scales. Concept retained here so it's not lost.
DeferredRevisit when team capacity warrants it. Dan to add to future agenda.
⏸ Deferred
25
Opportunity
COI Archetype Framework · Widen Beyond Trust-Advisor Categories
The Mar 16 design call named attorneys, CPAs, bankers, wealth managers, insurance brokers as canonical COI categories (per Appendix · COI Referral Fee Structure). Two of two COI calls in calibration are with NONE of those archetypes. Kevin / Tenstreet: operator-vendor + strategic acquirer + network-density node (~5,000 trucking clients, ~500K monthly active drivers, ~2 acquisitions/year). Evan / Armstrong: market-research authority + buy-side M&A advisor (~4,000 company profiles, ~4,000 buy-side outreaches/year). Both are also bidirectional — they refer sellers TO Next Mile AND represent buyers FOR Next Mile sellers. Current playbook treats COIs as one-way referral sources. The canonical list may be aspirational rather than operational.
DiscussAre Tenstreet and Armstrong outliers, or representative? Both came via warm intros — does cold outreach actually produce attorney/CPA COIs? If the canonical list is wrong, was it aspirational or did it reflect a different prior reality? See Appendix · COI Matrix.
◐ Discuss
27
Obstacle
Structured Referral Ask · Two-Call Pattern of Skipping It
The COIs · Conversation script includes a defined structured ask — "Who else in your book / mandate list is in a similar conversation right now?" — as the moment that surfaces live referrals. Two of two COI calls failed to execute it. Call-03 (Kevin): not asked. Kevin volunteered a referral anyway (the hardware deal at call min 44:05). Call-04 (Evan): not asked. Armstrong has 4 active buy-side deals (2 in freight brokerage) that are potential matches for current Next Mile sellers — nobody surfaced that on the call. Pattern, not individual coaching gap. Open: is it the script (clunky), the timing (when), or the discipline (not habituated)?
DiscussIdentify failure mode. Decide: hard-stop checklist item at end of every COI call, or informal coaching? Risk: could feel transactional, especially with non-canonical COIs. Possibly test 2–3 script variations across next COI calls before committing.
◐ Discuss
28
Obstacle
COI Referral Attribution · Verbal-First, Paperwork-Second
Call-03 (Kevin/Tenstreet), call min 44:05 — Kevin volunteered the hardware deal verbally, mid-call, with no signed referral agreement. The qualification rules in Appendix · COI Referral Fee Structure state: "Referral agreement executed by the COI before the first introduction is acted on." Strict reading: Kevin doesn't get 20% on the hardware deal. In practice, refusing to pay would damage the relationship — and the relationship is the asset. The bright-line policy doesn't survive contact with how real COIs operate. Need a "verbal referral → trigger paperwork within X business days → attribution applies retroactively" track.
DiscussDecide whether to amend qualification rules in Appendix · COI Referral Fee Structure to allow retroactive attribution under defined conditions. Open: timeline (5 days? 10?), prevention of late-paperwork abuse, paperwork trigger owner (Wally / Dan). Live test case: Kevin/Tenstreet hardware deal if it closes.
◐ Discuss
30
Opportunity
Mike → Wally → Ron Role Definition · Name It Explicitly
Calibration shows a working division of labor not yet documented. Mike: strategy, deep-seller calls, valuation analytics, founder voice. Wally: relationship voice, COI lead, peer-credibility unlock (exit story operates as trust-builder operator-to-operator). Carried Call-04 when Mike dropped from Zoom. Ron: analyst seat, financial/structural questions. First documented analyst-seat moment on a prospect call: Call-06 (Travis/Xtreme) min 18:59, captive-insurance equity-treatment question — technically correct, well-timed. Playbook currently positions Wally as "primary on Sellers and COIs (operator credibility)" — but data suggests cleaner division is Wally = COI lead + relationship voice, Ron = analyst seat + financial backbone, Mike = strategy + deep-seller calls.
DiscussLeadership working session. Confirm or revise role descriptions. Does Wally agree? Was prior framing aspirational? Decide whether to name explicitly in playbook (front-matter "Who Does What" section) or keep informal. What does Ron need (training, tooling, deal exposure) to be operationally independent?
◐ Discuss
32
Opportunity
Vendor Transition · Second Mile finished, Spoke begins
Two specialists, two different lanes — and the team's mental model of who does what needs to update. Sara Wolfe Vaughan at Second Mile delivered the HubSpot Marketing Hub setup and the full TIA campaign. That work is complete. Ciara Brewer at Spoke Marketing leads the Sales Hub stand-up per the May 26, 2026 quote: kickoff May 27, 6-week Mike-first build, 10-stage deal pipeline, custom properties, Mike's cutover end of Week 2, Wally operational by Week 4, full system live Jun 30. First-60-days commitment: $15,000 (per the refined May 26 quote, supersedes the Apr 30 SOW). The playbook references that need updating to reflect Spoke as the current marketing partner are scattered — this O&O is the trigger to do that write-up work.
DiscussConfirm the handoff is complete from a leadership standpoint. Identify the playbook references that still mention Second Mile and update them to Spoke. Decide whether Sara's contributions to the foundation need a "previously" attribution somewhere so the institutional record is honest.
◐ Discuss
33
Opportunity
Sales Activity Flywheel · Refresh against calibration data
The post-TIA conversion wave produced real evidence that the flywheel is turning. Five-plus named seller conversations now live in Stage 02 Engagement: Boost Transport (Justin · Atlanta brokerage), Travis at Xtreme (thawed · agreed to next call), Tim Quirk via Mark Drabe (referral fee in play), Donald McDonald (former employee turned COI · two seller intros), Chad Caldwell (LOI from another buyer · we got him to hold off and shop). Plus the $26M active deal at Stage 04 with Bruce at UTS. The flywheel framing in the playbook predates the calibration analysis. Now that we have call data on what actually happens in those conversations, the framing may need to update: which activities actually generate the next stage, what the trigger language looks like, what the post-call cadence should be. Worth examining whether the existing flywheel diagram captures the operational reality the calibration data revealed.
DiscussBring the existing flywheel framing to a leadership session. Compare against the patterns in the Phase 1 call summaries (Sellers + COIs). Identify what holds, what shifts. Decide whether to update the flywheel diagram in the Sellers spine or write a new one.
◐ Discuss
34
Opportunity
COI-Sourced Deal Path · Track and learn from Craig Helmrich → FreshX
The first major named COI relationship is producing. Craig Helmrich (transportation attorney, ex-Scopelitis, 300 clients followed him during COVID) was met at Howden night at TIA. He is already referring: FreshX, a technology producer pivoting to 4PL. The Black Belt buyer database has at least two viable destinations — Kevin Nadeau (active 4:30 call) and 10 Street. A real COI → seller → buyer path traveling through the engine for the first time. The system that exists on paper is producing. This O&O is the trigger to learn from it: what about the Craig Helmrich relationship made it work, what should we formalize, what mechanics deserve to become repeatable patterns in the COI play. Don't let the first end-to-end success pass without extracting the playbook update.
DiscussDebrief the Craig Helmrich relationship with Wally. What was the conversation arc that produced the FreshX referral? What does the COI play need that we didn't have when this started? Cross-reference the patterns with the Phase 1 calibration findings (especially O&O #25 widening the COI archetype list and O&O #29 directional tracking).
◐ Discuss
35
Obstacle
External-Event Newsjacking Emails · Low response on Supreme Court ruling email
An email sent to the Sellers database tied to a recent Supreme Court ruling had a notably low response rate. The leadership question is whether this is a problem with this specific email (timing, audience match, content) or with the email type: external-event newsjacking aimed at the T&L owner database. T&L founders may not engage with macroeconomic / regulatory content the way other audiences do. Or the email may have landed wrong for tactical reasons (subject line, send time, list segment). Without examining it as a category, we may either keep producing low-yield content or kill a content type that could work with refinement.
DiscussPull the metrics on the Supreme Court email (opens, clicks, replies, unsubscribes). Compare against other email types sent to the same audience in the same window. Decide whether newsjacking external events is a content type worth keeping for this audience, modifying, or retiring. Cross-reference with the broader content-mix discussion in the Sellers play (Campaigns & Assets).
◐ Discuss
36
Opportunity
Operating System Adoption · Bloom Growth OS scope and sequencing
The team currently operates against one of Bloom Growth's 8 Essentials — the Meetings essential, via the bi-weekly leadership meeting using the Bloom Weekly agenda and the 3D method (Discover → Discuss → Decide). The other 7 essentials (Growth Plan, People, Sales & Marketing, Finance & Data, Process, Technology, Elevate Relationships) are either implicit, partial, or absent. The Growth Plan section in particular has named gaps: 5-Year Vision not drafted, 1-Year Plan not cascaded (overlap with O&O #7), Quarterly Priorities not formally set, Core Values not crystallized, Ideal Leadership Team Structure partial. The leadership question is how much of the framework Next Mile formally adopts — three viable paths: (A) engage a Bloom Growth coach for full Day 1 facilitation and the 2-year journey, (B) self-implement using the Day 1 Facilitation Guide internally, or (C) selective extraction — keep what's working, formalize specific elements through existing leadership cadence. See The Operating System tab · Section 7 for the path-by-path framing.
DiscussBring to a leadership working session. Decide: do we formally name Bloom Growth OS as Next Mile's operating system framework? If yes, which path (A/B/C)? If C, which essentials get formal treatment and in what sequence? Cross-reference O&O #7 (1-Year Goal Cascade), #8 (Math), #12 (Accountability Matrix), #30 (Mike/Wally/Ron roles) — all of which fold into the Growth Plan and Ideal Leadership Team Structure essentials if Bloom is formally adopted.
◐ Discuss
37
Opportunity
7 Stages of a T&L Owner's Journey · Promote from canon to discussion item
The 7-stage T&L Owner's Journey lifecycle (Founding → Building → Growth → Maturity → Exit Window → Exit Process → Post-Exit) is referenced as established canon throughout the playbook — in the Sellers spine (Strategic Framework section), in the COIs spine (Stage-Vendor Map), in the Appendix (TIA Handout · The T&L Owner's Journey card). It also appeared on the customer-facing TIA handout distributed at Booth #218. But the leadership team has not formally discussed, validated, or locked the 7-stage framework. It was drafted and used. That's different from being agreed-to. This O&O surfaces it as a Discuss item so the team can: confirm the stage names are right, confirm Stage 4–5 (Maturity into Exit Window) is the primary territory we operate in, confirm the 10 mindset triggers that move someone from Stage 4 to Stage 5 are the right ones, confirm the framework drives the COI Stage-Vendor Map correctly, and decide whether anything needs to change before the next round of customer-facing materials are produced.
DiscussBring the 7-stage framework to a leadership session. Cross-check against the calibration data (Bruce/UTS, Chad/FL, Travis/Xtreme — where did each fall in the 7 stages?). Confirm or revise. If changes are needed, cascade them through the Sellers spine, the COIs spine, the Appendix TIA Handout card, and any new customer-facing materials. Cross-reference with O&O #20 (Experienced Acquirer dimension) — the personas overlay may interact with the stages.
◐ Discuss
38
Obstacle
Owens Corning concentration risk · UTS deal valuation question
Surfaced May 26 (Ron, with Jay): Bruce’s largest account at UTS is Owens Corning. Fitzmark also services Owens Corning — but a different region and a different plant from UTS’s footprint. Fitzmark’s stated position: “not going to be an issue, won’t affect valuation.” Ron’s read: real risk worth watching. The deal is in Stage 09 Diligence with data room open and a closing target before fall busy season. If the concentration question surfaces in diligence, it could compress valuation or extend timeline.
DiscussWally + Mike: confirm the Owens Corning regional/plant separation in writing from Fitzmark before final close. Document the customer-by-customer concentration profile for UTS in the data room proactively (don’t wait to be asked). Identify any other accounts where customer concentration could become a diligence question across the active pipeline (UTS, Caldwell Freight Logistics, Map Parcel, Challenger Freight).
○ Discuss

Discuss leads to decision. The next section holds items the team has talked through and now needs to approve.

Section C
Close to decision

In Approval.

3 items the team has discussed and is ready to decide on. These need a clean confirmation in a leadership session and then move to Solved with a write-up in the Appendix. The longer something sits in In Approval, the more likely it should be re-opened to Discuss — decisions worth making are worth making in a reasonable timeframe.

01
Obstacle
CRM Implementation · Spoke HubSpot Sales Pro Set Up
Spoke Marketing (Ciara Brewer) has issued a refined quote (May 26, 2026 · Ref 20260526-064400744) for HubSpot Sales Hub stand-up plus the first 60 days of active support. Total: $15,000 all-in — $14,000 Implementation - Growth + $6,000 Training & Support (2 months at $3,000) less a $5,000 Strategic Partner Discount. Payment: $7,500 on receipt + $7,500 on Jun 30. Schedule: 6-week Mike-first build kicking off May 27. Mike cutover end of Week 2 (Jun 8). Wally operational by Week 4. Full system live Jun 30. Scope expanded vs. the earlier Apr 30 SOW: now includes lead pipeline + visual lead board* + lead scoring* + lead routing workflows + automated sequences* + playbooks* + full dashboard suite* + lead-to-deal handoff* + built-in calling with auto-logging*. (Asterisks = Pro-dependent items that build immediately upon Sales Pro upgrade confirmation.) Out of scope · Phase 3: Buyer campaigns (3A/3B/3C), landing pages, Portal↔HubSpot integration. Why this supersedes the Apr 30 SOW: the refined quote bundles the Build and the Retainer into a cleaner package, broadens the scope to capture the Pro-dependent automation work, and adjusts the timeline to a Mike-first 6-week cadence starting May 27 instead of May 4.
DecideBring to next meeting · approve the May 26 quote and trigger payment 1 ($7,500). Confirm Sales Pro upgrade. Pre-kickoff gates (SOW + invoice, field map & active deals from Dan, TIA list from John + campaign map from Dan) all need to land in Week 1 (May 27). Full scope detail in The Record · Spoke Marketing · HubSpot Sales Pro Set Up.
◐ In Approval
02
Obstacle
Referral & Engagement Agreements · Finalize
Both drafts exist. Confirmed Mar 30: neither has been formally shared with Mike + John. Must be finalized before any COI introductions are made — protects everyone, sets clear economics.
PendingDan compiles both this week · circulates to Mike + John for review · finalize before first COI intro.
◐ In Approval
26
Obstacle
Blind Seller Teaser One-Pager · Single Biggest Tactical Gap
On Call-03 (Kevin/Tenstreet), Wally surfaced the same problem twice — call min 25:38 and again at 49:14: "That's going to be our challenge is for us to, amongst ourselves, determine, boy, is this something that we should run by Kevin or not?" The mechanic Wally wants: a one-page anonymous teaser that a COI can forward to a decision-maker without naming the seller. This asset does not exist anywhere in the playbook. COIs · Campaigns & Assets lists the COI One-Pager (handoff script) but not a blind-seller teaser. This is the single most actionable doc addition from the COI calibration. Without it, every potential COI referral requires back-and-forth pinging with the COI. Specs: industry standard, mode, revenue band, GP%, customer concentration, geography. Built from the SIM but heavily redacted. Standard template that becomes Wally's default tool.
DecideApprove the build. Identify owner — John (content) or Natalie Nicole (template). Land template before next COI referral conversation. Cross-reference COIs · Campaigns & Assets. See Appendix · Brand Asset Inventory · BA1.
◐ In Approval

In Approval becomes Solved with a recorded write-up. The final section is the institutional record — decisions made, preserved as the firm's working memory.

Section D
Institutional record

Solved.

6 decisions the leadership team has made and committed to. Each is the headline-level record; full write-ups roll up into the Appendix · Section A (Decisions Log) where the math, the rationale, and the criteria for revisiting all live. Solved items stay visible here so the team doesn't have to re-decide things it already decided.

13
Obstacle
Fee Structure Selected
Solved Mar 16. Final fee schedule: 1% of trailing-12 revenue OR 3.5% EV up to $30M + 2% above (whichever is greater). Subscription tracks at $500/$1,000/$4,000 per month with portal access. All consulting fees credited against final M&A success fee at close.
ResolvedFull schedule documented in Appendix A. Lehman Scale (Double) listed as alternative under discussion.
✓ Solved
14
Obstacle
COI Referral Fee Structure
Solved Mar 16. 20% standard fee · 10% reduced fee. 6-month signing window. Portal exception (if prospect enrolls in consulting/portal and later sells, fee is still paid). Qualification criteria defined: bonafide lead, legitimate relationship, formal introduction.
ResolvedSee Appendix A · COI Referral Fee Structure for full detail.
✓ Solved
15
Obstacle
Email Launch Sequence Defined
Solved. Staged release executed: Tier 1 Group 1 (Mar 31), Group 2 (Apr 1), Group 3 (Apr 2). Pre-show blast to Past TIA Apr 7–8. Post-show follow-up Apr 16. ~3,471 known contacts deployed across 9 segments.
ResolvedCampaign executed. Post-show ZoomInfo waves (Apr 22 / Apr 29 / May 6) framed as optional · pending list validation.
✓ Solved
16
Obstacle
CRM Selection
Solved. HubSpot Marketing Pro confirmed for early-stage marketing. WhatConverts for call tracking. Mike's homegrown CRM for active deal entry. HubSpot Sales Pro to absorb deal stages once stage-to-system mapping is locked.
ResolvedArchitecture decided. Live build of Sales module is the active workstream (Obstacle 01).
✓ Solved
17
Obstacle
Website Platform
Solved. WordPress confirmed for speed-to-launch. Scheduling engine (QR code → meeting request form) integrated for TIA show. Hosting decision documented — Marketing Hub Pro setup runs independently. HubSpot CMS migration (Option B) recommended for v2 to remove the seam.
ResolvedSee Appendix A · Hosting & Marketing Hub Setup for full detail.
✓ Solved
18
Obstacle
Geographic Focus · No Restriction
Solved. Next Mile M&A will not limit to a specific region. National North America focus with TIA Capital Ideas as the primary launch audience. Southeast preference noted but not a constraint.
ResolvedReflected in all Stage and Targeting language.
✓ Solved
Department · Overview

Overview.

Who is on the team, where we are on the roadmap, and how we got here. Built from six alumni interviews and Story on Purpose's Hero's Journey foundation. Updated every two weeks on the day of the leadership meeting.

Section 1
The foundation

Hero's Journey.

Why this firm exists and who it's for. Built with Story on Purpose from six alumni interviews. The conceptual foundation that anchors every play, every stage, every script in this document. When something in the playbook feels disconnected from purpose, this section is where you re-anchor.

How We Got Here · The Hero's Journey

The narrative spine underneath every play.

Built from six alumni interviews, distilled by Story on Purpose. The hero is the founder. The villain is what's keeping them stuck. The guide makes the difference between drift and outcome. Every Stage Play in the Playbook section draws from this foundation.

1
The Hero

The transportation lifer.

55+ years old. Multi-decade career in T&L. Built the company from nothing, often with a partner. Asset, asset-lite, or non-asset, $20M–$250M in revenue. Cares about employees, customers, and the legacy they're leaving. Wants the best value, but value means more than price: who the buyer is, what happens to their people, what the next chapter looks like.

2
The Villain

Time, pressure, and the wrong M&A firm.

Afraid they'll miss the timing window. The business is a drain on their emotions. Worry about what happens to employees post-sale. Changing technology (AI, driverless vehicles, electrification). Rising costs above what the market will bear. Legal threats. Capacity volatility. Annoyed by M&A solicitors with zero transportation experience who treat them like another car on the lot.

3
The Guide

Operators who've sat in the seat.

Founding Partner and Managing Partner with 90+ years of T&L experience between them. Decades in C-level transportation management and M&A. Sell-side only. Proprietary software. Process that compresses diligence. Database of 300+ strategic buyers. No upfront fees. Success fee only at successful close. One alumnus (Wally) became a partner. Every closed deal has a positive testimonial letter.

4
The Outcome

Financial legacy. Peace of mind. Freedom of time.

A successful sale that hits the goals that mattered: financial, people, strategic. Confidence and pride in the legacy. The buyer was the right match. Customers and team in good hands. Less time with lawyers and accountants. Less cost to the seller. Freedom from being chained to the business. The firm did what it said it would do.

That's the foundation. Below: where the operating system currently stands, what's running, what's in flight, and what's sequenced for later.

Section 2
Current state

You are here.

The roadmap snapshot. Where the engine is in its build-out, which audiences are active, which are sequenced for later, and what the leadership team is working on right now. Updated every two weeks at the leadership meeting.

You Are Here

Three phases on a timeline.

Phase 1 (Built · late 2025 → May 2026) shipped: alumni interviews, narrative foundation, brand & site, HubSpot Marketing Pro, the TIA campaign. Phase 2 (Building · May 27 – Jun 30, 2026) is in flight: HubSpot Sales Hub stand-up with Spoke — Mike-first, cutover end of Week 2, full system live Week 6 (per May 26 quote). Phase 3 (Activating · summer 2026 → 2029) spreads the remaining plays and runs the full four-play engine.

Phase 01 · Built
Late 2025 → May 2026

Foundation Shipped

Source material captured. Narrative built. Strategy defined. Brand & website launched. Tradeshow materials produced. TIA executed.

  • Late 2025 · Source material
  • 6 alumni interviews captured (Doug · Ross · Wally · Roger/Deanie · Dan K · Carol)
  • Late 2025 → Early 2026 · Narrative foundation (John · Story on Purpose)
  • Hero's Journey narrative framework
  • Exit Readiness Library scoped (5 categories, ~28 titles)
  • Standard CTA defined ("Schedule a Confidential Conversation")
  • Jan – Feb 2026 · Strategy & architecture
  • ICP & segmentation defined
  • 4-play architecture (Sellers · COIs · Buyers · Portal)
  • Seller tier framework (Cold · Early · Ready · Not Yet)
  • 11-stage Buyer Journey defined
  • COI strategy launched (Targeted, In Conversation, Engaged · 20% referral fee)
  • Feb – Mar 2026 · Brand, identity & website
  • Next Mile M&A brand identity & positioning (Natalie Nicole)
  • nextmilema.com built and launched
  • Mar – Apr 2026 · Marketing tech & tradeshow materials
  • HubSpot Marketing Pro live (Sara · Second Mile)
  • 9-segment TIA email campaign executed
  • April 15, 2026 · The show
  • TIA Capital Ideas show launched · activity generated
  • May 2026 · This month
  • Revenue Execution Engine Playbook · Vol. 1 No. 1 shipped
2
Phase 02 · Building
May 27 – Jun 30, 2026

System Stand-Up

Mike-first 6-week build. Sales Pro live. Deal pipeline + record layouts Day 1. Mike operational end of Week 2. Wally operational by Week 4. Full system live Week 6.

  • Wk 1 · May 27 · Mike's foundation
  • SOW + invoice · field map & active deals to Ciara
  • HubSpot Sales Pro upgrade signed by Jay · Pro tier unlocks sequences, visual lead board, automation
  • Mike exports current email templates · via test-email method to Dan + Sierra (export-to-Mac path was blocked)
  • Kick-off overview call · Sierra + Mike + Wally · confirm training schedule
  • 10-stage deal pipeline · custom properties · up to 3 record layouts
  • Active deal records imported · lead status configured · bounce cleanup
  • Mike training 1 (deal board)
  • Wk 2 · Jun 2 · ◆ Mike cutover · Wally foundation
  • 4 email templates · document library · lead routing workflows
  • Visual lead pipeline board* · lead-to-deal handoff* (Pro)
  • Mike training 2 (daily workflow) · Wally training 1 (contact entry)
  • Wks 3 – 4 · Jun 9 – Jun 16 · Automation
  • Database segmentation · company + contact object setup · basic pipeline report
  • Automated sequences* · lead scoring* · playbooks* (Pro)
  • Wally training 2 (sequences*) · both training 4 (playbooks*) · ◆ Wally operational
  • Emergency-support channel with Sierra defined · email + text routing for time-sensitive deal questions · same-day response (per Wally’s June 10 ask)
  • Wks 5 – 6 · Jun 23 – Jun 30 · Dashboards & steady state
  • Full dashboard suite* (Wally's daily · Mike's pipeline · lead source attribution)
  • ◆ Full system live
  • Through Week 6 · Ongoing
  • 30-min weekly office hours (60 days, both Mike + Wally)
  • John: Exit Readiness Library production-ready · Phase 3 scoping begins
  • Referral & Engagement agreements finalized · bounced contact reactivation
You are here
3
Phase 03 · Activating
Summer 2026 → 2029

Full Engine Running

All four plays in motion. 12-deal annual cadence.

  • Jun – Jul 2026 · COIs play activates
  • Load COI campaigns into HubSpot (Targeted, In Conversation, Engaged)
  • Jul – Aug 2026 · Buyers play activates
  • Load Buyer campaigns into HubSpot (Known Database, Met at TIA, Engaged on Current Deal)
  • P03 Buyers content engine producing comparables monthly
  • Fall 2026 · Portal (inside Sellers)
  • Portal scoped & deployed (inside Sellers) (Population A off-ramp · Population B subscription)
  • Ongoing → 2029 · 3-year vision
  • Full Bloom Growth engagement (if cadence proves out)
  • Hit 12 closed deals / year (3-year vision)

You Are Here shows the timeline. The Completeness Map below shows the same picture in a different cut — what’s built, what’s in flight, what’s sequenced for later.

Section 2b
Honest state of the doc

Completeness map.

Some sections are complete and validated; others are structurally in place but awaiting content from the call-analysis loop. This map tells you what state each section is in, so you know what you’re reading. Paired with You Are Here above.

For the reader

Completeness map.

This document is in active build. Sits paired with You Are Here above as the two complementary views of where we are. Some sections are complete and validated; others are structurally in place but awaiting content from the call-analysis loop (Mike's recorded calls + Wally's incoming conversations). This map tells you what state each section is in, so you know what you're reading.

Complete
Structure built · content validated · ready to use
  • Overview · all five sub-sections built from six alumni interviews + Hero's Journey foundation
  • The Playbook · Master Flow · 11-stage journey diagram with Portal + Alumni branches
  • The Playbook · Stage cockpits · all 11 stages in cockpit format (Goal · Mindset · Flow · Assets · Checklist · Voice placeholder · Context)
  • The Playbook · Plays cross-references · every stage shows which plays feed it
  • Sellers narrative spine · 11 sections from Who → Voice → Journey → Triggers → Narrative → Conversation → Where → Influence → Plays → Portal → Running → Measure
  • Sellers · Cold Outbound play · full 8-element format (Strategy · Goals · Persona · Buying Stage · Discovery · Messaging · Objections · Assets)
  • Sellers · Portal section · two-population framing (off-ramp + buyer's-eye-view marketing hook)
  • Operating System · Tuesday meeting agenda, scoreboard, roadmap phases
  • Obstacles & Opportunities · active issues log
  • Appendix · decision archives
Pending · call analysis
Structure ready · content fills in from the 18 recorded calls + ongoing conversations
  • Sellers · Plays B–F · placeholder cards for Post-TIA Reactivation, COI Referral Activation, Engaged-Ready Nurture, Engaged-Not-Ready Re-Engagement, Alumni Referral Loop, Portal Engagement (Sellers Database)
  • COIs · all named plays · structure scoped (COI Outreach Targeted, COI Conversation Activation, Engaged-COI Referral Cadence, First-to-Know COI Activation), 8-element build-out pending
  • Stage cockpit · Voice of Prospect · the "From the Field" band in every stage. Currently placeholders; populated as recorded calls are analyzed
  • Stage cockpit · During-call checklists · the middle column of each Seller's Checklist. Currently templated; replaced with real seller language once calls are analyzed
  • KPI targets · framework in place for Sellers, COIs, Buyers; specific numerical targets pending baseline data from Q2–Q3 2026
Pending · Phase 3
Sequenced after Sellers + COIs mature · Fall 2026
  • Buyers · all named plays · Known Database Monthly Color, Met at TIA Onboarding, Engaged-on-Current-Deal, Buyer-side Referral Capture
  • Buyer database migration · 300+ buyers from Mike's system into HubSpot with proper segmentation
  • Portal · Population B productization · paid subscription model, onboarding flow, conflict-of-interest rules
  • Buyer-side voice of customer · interviews scheduled in Phase 3

How the loop closes. Calibration Phase 1 (5 sales calls: 3 Sellers, 2 COIs) landed in May 2026 — 13 calibration O&Os (#19-31) live in Obstacles & Opportunities, 8 new Appendix entries (5 call summaries · seller and COI matrices · brand asset inventory) live in the Appendix. Four additional O&Os (#32-35) promoted the bi-weekly field notes into formal discussion items: vendor transition (Spoke), flywheel refresh against calibration, the Craig Helmrich COI path, and the Supreme Court newsjacking email response rate. Two more (#36, #37) emerged from later passes: Bloom Growth OS scope and sequencing, and the 7 Stages of a T&L Owner's Journey promoted from canon to a formal Discuss item. The working list is now The Meeting tab (renamed from Obstacles & Opportunities, moved to tab position #2 right after Contents) — framed correctly as the engine of the Bloom Weekly Meeting. O&Os are organized by status into four sections (A Define · B Discuss · C In Approval · D Solved) with a sticky TOC; the topic grouping is available as a future view. The Operating System tab has been restructured into a seven-section narrative spine that documents the Bloom Growth OS framework, the 8 Essentials self-assessment baseline, the Growth Plan checklist (with honest "not yet / partial / present" status on each artifact), and the existing Goal/Math/Score content preserved inside the new framework. Overview is a four-section narrative spine matching the Sellers / COIs / Buyers pattern — no more sub-tab nav. Each "Pending · call analysis" item in the map above continues to fill in as more recorded calls are analyzed. Phase 2 (Buyer calibration · 3-5 buyer calls) is scoped as O&O #31 and is sequenced after the Buyers database migration. The bi-weekly leadership meeting reviews what's new from the analysis loop and what's been promoted from placeholder to validated.

The state is clear. Now: who's at the table executing it.

Section 3
The team

Who's at the table.

Named roles, named owners, named accountabilities. Mike, Wally, Ron, Dan, John, and the vendors who carry parts of the operation. When something in the playbook needs a decision, this section tells you who makes it.

Who's at the Table

The team that runs this engine.

Next Mile M&A is a sell-side-only M&A advisory firm focused exclusively on Transportation & Logistics. The firm represents founder-led T&L operators in the $20M–$250M range across asset-heavy, asset-lite, and non-asset models. The engine is run by a small leadership team supported by external execution partners.

Mike Bloss (Founding Partner) and Wally Brauer (Managing Partner) lead the firm. Together they bring 90+ years of combined Transportation & Logistics and M&A experience: Yellow Freight / YRC, Echo Global Logistics, and decades operating asset-based and non-asset businesses. Jay Roberts owns web and tech. Ron Buesinger reviews outbound before deploy.

External support: Story on Purpose (John Knicely) owns the Voice of Customer track and the Hero's Journey foundation that informs every play. Dan Klein Consulting facilitates the bi-weekly Revenue Leadership cadence, builds and maintains this living document, and drives campaign strategy. Natalie Nicole delivered the Next Mile M&A brand identity. Spoke Marketing (Ciara Brewer) is the active sales-side build partner: HubSpot Sales Hub, 10-stage pipeline, post-TIA contact triage, Wally and Mike training. Earlier phase: Second Mile (Sara Wolfe Vaughan) delivered HubSpot Marketing Pro setup and the TIA email campaigns.

Wally Brauer
Managing Partner · Next Mile
Seller & COI activation · outbound · operator credibility
Mike Bloss
Founding Partner · Next Mile
Deal lead · seller relationships · LOI & diligence
Jay Roberts
Web & Tech · Next Mile
nextmilema.com · WhatConverts · digital infrastructure
Ron Buesinger
QA · Next Mile
Outbound review · pre-deploy gate
John Knicely
Story on Purpose
VOC · Hero's Journey · Exit Readiness Library
Dan Klein
Dan Klein Consulting
GTM strategy · revenue leadership cadence · this document
Natalie Nicole
Brand · delivered
Next Mile M&A brand identity
Ciara Brewer
Spoke Marketing
HubSpot Sales Hub · Phase 2 Build · Adoption Retainer
Sara Wolfe Vaughan
Marketing Hub · Second Mile · delivered
HubSpot Marketing Pro setup · TIA email campaigns

The team is the engine. The closing section is the proof — alumni in their own words on why they chose Next Mile and what mattered.

Section 4
The proof

Voice of the alumni.

Verbatim from sellers who closed deals through Next Mile. These quotes anchor every part of the playbook downstream — when a script invokes a phrase like "diagnostic posture" or "only sellers," the language comes from these alumni telling us in their own words what mattered. The full alumni interview corpus is the source of the firm's Voice of Customer.

Voice of the Alumni

In their own words.

Five alumni interviews. Five transactions closed. Quotes sourced verbatim from the source transcripts. Each one anchors a Stage Play in the Playbook section.

"I would absolutely advocate that you consider Black Belt. In fact, not even just consider them, just go with them."

Dan Krivickas American Group

"They led me straight into a big warm kiss instead of a hard damaging punch."

Doug Hazen AMAC

"You don't know what you don't know. It was really great to have someone in the corner that knew."

Ross Bodenheimer Sutton Transport

"Mike was really good at walking us and me through the process, through the information, and building a data room in advance of even marketing us so that when we went to market, a lot of the diligence was already pre-built."

Roger Harrison FreightLink / Sutton Transport

"I wanted them to really be in good hands when we made this transition."

Department · The Stack

The Stack.

How the revenue engine is wired — the systems, the data flow, the tools. Two views: Architecture shows the static picture (where everything lives, how it connects). Call Flow shows the live process (what happens when Mike or Wally takes a sales call, and what Claude does between meetings). Built to anchor the tech conversations with Jay and to make the engine visible to anyone who needs to understand it.

Section 1
The static picture

Architecture.

Seven layers. Read top to bottom. Three audiences (Sellers, COIs, Buyers) flow into one engine, get nurtured through HubSpot Marketing Pro, convert into the 11-stage pipeline in HubSpot Sales Pro, and feed an analysis loop that updates this playbook every two weeks. The dashed lines are bidirectional flows — the Portal feeds back into the pipeline when a "not yet ready" seller is ready; Claude reads HubSpot data and writes back into this document.

01 · SOURCES 02 · ENTRY 03 · CAPTURE 04 · NURTURE 05 · PIPELINE 06 · INTELLIGENCE 07 · THE PLAYBOOK Sellers T&L founder-operators COIs insurance · finance · attorneys Buyers 300+ strategic acquirers nextmilema.com WordPress · hosted by Beanstalk Forms Schedule a confidential conversation HubSpot Marketing Pro campaigns · lists · segmentation Sellers nurture Cold · Engaged Early Ready · Not Ready Exit Readiness Library COI nurture Tier 1 · In Conversation Engaged 20% referral fee Buyer comms Known Database Met at TIA Phase 3 Portal "Not yet, not no" sellers paid subscription off-ramp & loop HubSpot Sales Pro · the 11-stage pipeline 01 Prospecting · 02 Engagement · 03 Education · 04 Evaluation · 05 Preparation · 06 Market 07 Connected · 08 LOI · 09 Diligence · 10 Transition · 11 Referral Engine each stage carries its play: mindset · assets · checklist · script Call recordings · transcripts Fathom · Read.ai · auto-routed to HubSpot contact / deal record Claude (Team) reads HubSpot · analyzes calls · updates this doc The Revenue Execution Engine playbook this document · updated every two weeks · sharpens with every call
What to point at

For Jay: this is the diagram that explains why marketing went first (layers 02–04), why CRM is happening now (layer 05), and what Claude is doing (layer 06). The HubSpot Sales Pro upgrade is what unlocks layer 05 — sequences, the visual lead board, the automation layer. For Mike + Wally: notice that everything you do during a call eventually lands in layer 05 (the deal record), which feeds layer 06 (Claude reads the calls and updates this doc), which closes the loop in layer 07.

Architecture is the static picture. Call Flow is what actually happens when one of Mike or Wally takes a call.

Section 2
The live process

Call flow.

What happens when Mike or Wally takes a sales call — from calendar invite to deal advancement, with the parallel Claude analysis loop running between meetings. The left rail is what the human does. The right rail is what Claude does in parallel. The dashed lines connecting them are the data flows — recordings going out, playbook updates coming back.

CALL SCHEDULED STEP 01 Open Playbook → find the stage "Where is this deal? What's the play here?" 5 min · before every external call STEP 02 Pre-read the play Mindset · assets · checklist · script Match what they're feeling. Open with what they need. STEP 03 Check HubSpot record Contact exists? If not, create. Note last touch. STEP 04 · THE CONVERSATION Take the call Note-taker joins automatically (Fathom / Read.ai) Follow the script. Honor the mindset. Push back on optimistic narrative. Diagnose, don't sell. STEP 05 · WITHIN 60 MIN Post-call routing → Recording & transcript route to HubSpot record → Log next steps & tasks → Update deal stage if it shifted → Send the matching HubSpot template (mid-funnel asset) Stage advance triggers marketing automation (see Step 06) STEP 06 · AUTOMATION Marketing triggers at stage transition Next nurture email · sequence step · portal off-ramp DEAL ADVANCES · NEXT CALL SCHEDULED CLAUDE · ANALYSIS LOOP What happens between meetings A · INGEST Read transcripts from HubSpot B · ANALYZE Run each call against the play Mark what's wrong / missing / new C · SURFACE New O&Os for the meeting Pattern signals across calls D · UPDATE Refine mindset / assets / script Ship new issue of the doc recording playbook updates next issue
The non-obvious bit

Most of this looks ordinary — take a call, take notes, file them. The recording → transcript → HubSpot routing in Step 05 is what makes the loop close. Without auto-routing, the transcript sits in a folder somewhere and Claude can't see it. Once it's on the deal record in HubSpot, Claude reads it, runs it against the play, and the playbook gets sharper. This is why the meeting-transcription decision matters more than it looks — it's the upstream input that everything else depends on.

Department · The Operating System

The Operating System.

For leadership. The Tuesday bi-weekly meeting infrastructure. North-star goals, weekly Scoreboard, the roadmap, the team. This is what runs the business between issues. Updates land every two weeks on the day the leadership team meets.

Section 1
How we're operating today

The Bloom Weekly Meeting.

The Next Mile leadership team currently operates against one of Bloom Growth's 8 Essentials: the Meetings essential, expressed through the bi-weekly leadership meeting. The agenda below is the Bloom Weekly Meeting structure, ~90 minutes, with the 3D method (Discover → Discuss → Decide) for working the O&O list. Treat this section as the documented version of what the team is currently doing.

1
Check-in
Share what has been most meaningful personally and professionally in the last 7 days, and your feelings about it.
2
Quarterly Priorities
Quick review of the most important special projects. Identify if any are off track, stuck, or need help. Anything requiring discussion gets added to the O&O List.
3
KPIs
Leading indicators (activities, not results). The weekly metrics that give insight to course-correct in real time. Not yet implemented at Next Mile.
4
Headlines
Company news about customers, employees, vendors. 90% positive. 10% bad news becomes O&Os. Target: 3-4 headlines per week.
5
To-dos
One-week action items. The most sacred and important promises made between meetings. Goal: 90% completion every 7 days.
6
O&O List · 3D Process
A list of all opportunities and obstacles the team prioritizes and problem-solves for ~60 minutes each week. At least one O&O added per leadership team member. Sorted most-recent-first; team chooses top 3 by importance (not urgency, not interest, not ease). Each O&O moves through three stages:
D
Discover
State the issue in 1-2 sentences with the outcome needed. Identify root cause. Identify the decision owner. Go slow.
D
Discuss
Keep discussion focused on the requested outcome. Open, honest, vulnerable. Everyone participates regardless of seat. Don't go in circles. Go fast.
D
Decide
Inspiring, permanent solution. Every action becomes a specific To-do. Six common decision types: change process · change person · change strategy · stop doing · delegate · automate.
7
Wrap-up
Each team member shares the most valuable part of the meeting and one thing to do better next time.

The Bloom Weekly Meeting is one of Bloom Growth's 8 Essentials. Next: the full framework — what the other 7 are, and where Next Mile stands against each.

Section 2
The Bloom Growth OS framework

The 8 Essentials.

The Bloom Growth Operating System defines 8 essentials that together make an organization run well. Each has a what, a why, and an outcome, and is rated on a 1-10 scale at the leadership level. The self-assessment baseline below uses Bloom's exact framing — the ratings, when the leadership team is ready to do them, are an honest snapshot of where the firm stands.

01
Growth Plan
Creation, documentation and enrollment in our future.

What: A Growth Plan for the future of the organization.

Why: If we're not on the same page about where we're going, it's unlikely we'll get there.

Outcome: All the energy in the organization aligned around our most important ideal future.

Baseline question
"How aligned is everyone around your growth plan?"
10 = all employees aligned, working toward common goal · 1 = high misalignment, not on the same page
Status: not yet rated
02
People
Right People, Right Seats.

What: Right people in the right seats throughout the organization.

Why: With the support of teammates, customers, and vendors, anything is possible. Great people can experience growth and stay.

Outcome: Working with people we love and respect, having fun while achieving business goals.

Baseline question
"Are right people in the right seats throughout the organization?"
10 = everyone fits culture and succeeds in their role · 1 = many don't fit culture or aren't finding success
Status: not yet rated
03
Sales & Marketing
Attracting new and growing existing clients and customers.

What: Taking proactive steps to achieve growth goals.

Why: All organizations work to attract new clients. Many don't give enough attention to growing and retaining existing ones.

Outcome: Predict growth and achieve the growth target.

Baseline question
"How effective are you at attracting new and growing existing clients?"
10 = growing as fast as we want · 1 = we have room to grow
Status: this is the area the Revenue Execution Engine playbook is built to operationalize · self-assessment recommended quarterly
04
Meetings
Love your meetings.

What: Meetings are the glue that holds execution and communication together — organizing inputs and capturing outputs.

Why: Historically meetings suck. There's a better way to make them enjoyable and effective.

Outcome: Fewer meeting minutes, more effective meetings. Getting more done in less time.

Baseline question
"How enjoyable, effective and productive are all of your internal meetings?"
10 = start on time, end on time, productive, fun, get things done · 1 = meetings suck
Status: this is the essential Next Mile is currently operating against · the Bloom Weekly Meeting agenda (Section 1) is the implementation
05
Finance & Data
Enabling proactive decisions.

What: Tools for getting the right data at the right time to enable proactive decisions.

Why: Slow-growing businesses can use historical financials. Fast-growing businesses need leading indicators — tracking activities that come before results.

Outcome: Weekly KPIs that directly impact quarterly and annual growth goals. Leading indicators that allow real-time course correction.

Baseline question
"How well does your finance and data information enable proactive decisions?"
10 = all the time · 1 = never
Status: not yet rated · the KPI framework section of the Bloom Weekly is currently unimplemented at Next Mile
06
Process
Improving the speed and quality of recurring tasks.

What: Agreed-upon, documented best practice of recurring tasks throughout the business.

Why: 80-90% of teammates' time is spent on recurring tasks. Optimizing process has massive impact on productivity, consistency, and quality.

Outcome: 80% of recurring tasks documented and systematized, with 10-20% efficiency or quality gains measurable.

Baseline question
"Do we have a documented process (best practice) for recurring tasks that ensures speed and quality?"
10 = processes improving speed and quality across the board · 1 = no agreed-upon documented process, consistent breakdowns
Status: not yet rated · the 11-stage Playbook (PB tab) is the closest current artifact
07
Technology
Internally optimized, externally leveraged.

What: Technology that is internally optimized and externally leveraged.

Why: Internal tech needs to be effective and simple to grow and scale. External tech makes it easy for clients to do business with us.

Outcome: Internal tech effective, simple, fully optimized; employees know how to use it. External tech makes it easy for clients to do business.

Baseline question
"How well is our internal and external tech serving us?"
10 = simple and effective · 1 = no plan, overlaps and duplications
Status: not yet rated · HubSpot Sales Hub build (in flight) is the major active workstream
08
Elevate Relationships
Having fun growing together.

What: A culture that fosters healthy relationships, allowing fun and productivity.

Why: High-performing teams have positive impact on client experience, productivity, and employee satisfaction.

Outcome: Teammates engaged, enjoying what they do and who they work with.

Baseline question
"How well are we doing in having fun growing this business with little to no drama?"
10 = quite well · 1 = not at all
Status: not yet rated

The 8 Essentials describe the operating system at the level of the firm. The Growth Plan zooms in on the first essential — and is the most prescribed of the eight.

Section 3
The first essential, in detail

The Growth Plan.

Inside the Growth Plan essential, Bloom defines specific artifacts the leadership team produces during Bloom Day 1 facilitation and refines through subsequent quarterly sessions. Each artifact below is either present, partially present, or absent at Next Mile today. This section is the honest checklist of where the firm stands.

Not yet

5-Year Vision · North Star statement.

A qualitative and quantitative statement of where the firm will be in 5 years. Includes a sense of scale or growth (often a number) plus a qualitative element that connects the team at the heart. Sometimes longer-horizon (10-year) for slower-growing businesses.

At Next Mile today: not formally drafted. The implicit working horizon is the 3-Year Target (12 closed deals per year by 2029) documented in Section 4 below, but Bloom's prescription is a richer qualitative + quantitative statement.

Partial

3-Year Target · operational picture.

What the business looks like in 3 years — concretely. Revenue, team, geography, named accounts.

At Next Mile today: 3-Year Target of 12 closed deals/year by 2029 is documented in Section 4 below. The fuller operational picture (team size, revenue, geographic footprint) is not yet locked.

Not yet

1-Year Plan · cascade from 3-Year.

Annual goals that cascade down from the 3-Year Target. SMART goals with owners and quarterly checkpoints.

At Next Mile today: not yet defined. This is the gap O&O #7 (1-Year Goal Cascade) and the WIP banner on this tab have been pointing at. Mike + Wally working session needed.

Not yet

Quarterly Priorities · 90-day projects.

The most important special projects for the next 90 days. SMART, with owners. 2-3 per leadership team member. Company priorities + Departmental priorities. Reviewed weekly in the Bloom Weekly Meeting.

At Next Mile today: not formally set as Bloom Quarterly Priorities. The O&O list contains many quarter-scale items but they're not organized as a deliberate quarterly priority set.

Not yet

Core Values · what we stand for.

The values that guide the team and the firm. In Bloom, these emerge from the Deeper Bond exercise (Bloom Day 1) where leaders share moments of pride and the themes that emerge become the foundation for the core value statements.

At Next Mile today: implicit core values are visible in the Hero's Journey work (Overview tab) and in the Sellers spine (the "diagnostic posture" principle, the operator-voice positioning). Not yet crystalized into formal Core Value statements.

Partial

Ideal Leadership Team Structure · 9-12 month picture.

Future-state org chart focused on functional roles, not people. Bloom prescribes three core functions: Get Work (sales + marketing), Do Work (operations / service delivery), Get Paid (finance + admin). Names get assigned later (Bloom Day 30).

At Next Mile today: the Mike → Wally → Ron division of labor is emerging informally (Mike = strategy + deep-seller calls, Wally = COI lead + relationship voice, Ron = analyst seat + financial backbone). Captured in O&O #30 as a Discuss item. Not yet a formal accountability chart.

Bloom Growth's framework describes the architecture. The next three sections capture the existing Next Mile operating content — Goal, Math, Score — which lives inside the broader framework above.

Section 4
Existing content

The Goal.

The current 3-Year Target and the in-flight progress against it. This content was built before the Bloom Growth framing was added — it sits inside the Growth Plan essential's 3-Year Target slot.

3-Year Target · 2029
12
Closed deals per year.
1 active in pipeline $26M weighted value 11+ deal gap to annual cadence
The Reality Check

What we have vs. what we need.

A clean read of where the pipeline sits today against the 3-year target. The 1-year cascade has not yet been set with leadership.

Today · May 9, 2026
  • 1active deal in market
  • $26Mweighted pipeline value
  • $40M3-year avg deal-size target
  • TBDavg time to close · need historical data
3-Year Target · 2029
  • 12closed deals per year
  • $10M+annual revenue
  • $40Mavg deal size
  • TBD2026 milestone target · open with Mike & Wally
The Hero

Who we're representing.

Founder-led T&L business owners somewhere on the exit-contemplation spectrum. They're buying clarity, not just a transaction. Source: Hero's Journey, Story on Purpose · Mar 2026.

Demographic
$20M–$150M Revenue
Founder-owned, age 55+. Considering exit in 1–5 years. May have a CFO or professional management team. Often not formally "for sale."
Geographic
North America
No regional restriction. Southeast focus under discussion. TIA Capital Ideas serves as primary launch audience. National coverage via 300+ buyer database.
Psychographic
What Drives Them
  • Fear of regret · making the wrong move
  • Desire for control · keeping options open
  • Trust before transaction
  • Concern for employees and legacy
  • Skepticism of generic M&A firms
The Narrowing

From the universe to a list you can call.

Generic ICP gives a universe. The TIA campaign already narrowed that into named segments — pipeline, buyers, past clients, past TIA attendees, engaged contacts, LinkedIn network, friends & family, and COIs by category. Post-TIA the conversation now has names and tags inside HubSpot.

Step 01 · Universe
~17,340
Total reachable contacts across the TIA campaign + ZoomInfo dataset.
Segment by signal
Step 02 · Pre-TIA Known
~3,471
Known contacts in HubSpot · current pipeline + buyers + past clients + past TIA + engaged + LinkedIn + F&F + COIs.
Show + follow-up
Step 03 · Post-TIA Warm
TBD
Booth visitors + scheduled meetings + Tier 1/2 COI conversations from Apr 15–16 · count to be loaded post-show.
Sellers Track · TIA Segments
Pre-TIA Known Contacts
~3,471 contacts deployed across 9 segments before and during TIA Capital Ideas — primary send list.
Segment Breakdown
Current Pipeline 151 records · Mar 31
Buyers List 295 buyers
TIA Attendees 426 (308 net new)
Past TIA Shows 1,809 records
Past Clients 16 records · VIP tone
Engaged · ZoomInfo + CRM ~230 records
LinkedIn Network 715 connections
Friends & Family 219 contacts
COIs by Category 36 across 5 tiers
COI Track · TIA Tiers
36 Identified COIs
10 must-meet Tier 1 + 2 targets prioritized for floor strategy. Day 1 was Tier 1+2 (~6.7 hrs); Day 2 was Tier 3–5 (~5.3 hrs).
T1 Insurance & Finance 10
T5 TMS & Core Tech 10
T4 Freight Tech / AI 6
T2 Staffing & BPO 5
T3 Data & Compliance 5
Tier 1 Targets · First to know an exit
Reliance Partners Insurance
Roanoke Insurance Insurance
Gallagher Insurance
Triumph · Relay Payments Finance
Gulf Coast Business Credit Finance
+ 5 more · Avalon, Verisk, PFA, LogistIQ Insurance · Finance
The Point The TIA campaign was the first big narrowing motion. Post-show, the names with engagement signals are the warm wedge into next-stage conversations. Post-show ZoomInfo waves (Apr 22 / Apr 29 / May 6) are framed as optional — to be activated only after list validation and warming through other channels.

Below the goal: the math that has to work for the goal to make sense.

Section 5
Existing content

The Math.

The pipeline math. Activity volumes, conversion rates, and the input-output relationship that produces the 3-Year Target.

The Math

From the goal to weekly activity.

The full chain. Working backwards from the 3-year target. Some operators are still TBD and need leadership input — flagged below.

Step 01 · From close cadence to LOIs
12
Closed Deals / Yr
÷
90%?
LOI → Close · TBD
=
~13
LOIs / Yr Needed
Source-Deck Inconsistency · Flag for Leadership

The deck's scoreboard targets 2 LOIs/quarter (= 8/yr) at a 90% close rate — which produces ~7 closes/year, not 12. Either the LOI cadence target needs to roughly double, or the close-rate assumption needs tightening, or the 12-deal goal is a 3-year endpoint that ramps from a smaller 2026 number. Resolve in next leadership working session.

Step 02 · Activity funnel · per the deck scoreboard
50
New Leads / Mo
×
15%
Response Rate
~8
Calculated · Deck says 12
12
Intro Calls / Mo · per deck
Step 03 · From intro calls to qualified opportunities
12
Intro Calls / Mo
×
40%
Conversion
=
~5
Qualified Opps / Mo
×
80%
Go Decision
=
~4
Engagements / Mo
Wally's Accountability Questions · Open Items

From the deck: "Are these conversion rates realistic for year 1?" / "How do we track deals that sit in 'Education' too long?" / "Who is responsible for weekly CRM updates?" / "How do we weight probability at early stages?" — These should be answered before this Math section gets confirmed. The numbers above are taken from the deck's scoreboard but have not been pressure-tested with closed-deal data.

The Reconcile

Where the deals come from.

Four plays, three sources of revenue (Sellers · COIs feeding Sellers · alumni network) plus the long-tail Portal. Sellers is the primary game; COIs is the highest-leverage assist. Buyers and Portal don't close deals directly but make everything else more effective.

Sellers · Primary
Sellers
Four tiers (Cold Targeted, Engaged Early, Engaged Ready, Engaged Not Ready). TIA-sourced + direct outbound + warm intros. Today's pipeline lives here.
TBD deals Set with Mike
COIs · Build · 30 days
COIs
Three tiers (Targeted, In Conversation, Engaged). 36 COIs mapped, 10 priority. 20% Y1 / 10% Y2 referral fee. Highest-leverage assist into Sellers pipeline.
TBD deals Q3 activation
Buyers · Build · 60 days
Buyers
Three tiers (Known Database, Met at TIA, Engaged on Current Deal). 300+ database. Doesn't close deals directly. Generates demand and comparables that energize Sellers + COIs.
Demand-side Comparables engine
Portal · Scope (inside Sellers)
Portal
Population A off-ramp (catches Engaged Not Ready sellers from Stage 04) + Population B paid subscription (markets to the wider Sellers database). Build status and timeline TBD.
Long tail Separate workstream
Always-On · Organic
Mike's Network
Wally's relationships, alumni references (Doug, Ross, Wally B., Harrisons), inbound from past TIA attendance.
TBD deals Steady contributor
Total reconcile
12 deals · $10M+ revenue · ~$40M avg
Channel split TBD with leadership

And below the math: the scoreboard. What we measure weekly.

Section 6
Existing content

The Score.

The Bloom Weekly KPI scorecard. In Bloom's prescription this is the leading-indicator dashboard reviewed every weekly meeting; at Next Mile today it's scaffolding awaiting the HubSpot Sales Hub build that makes the data live.

Year-to-Date

What's happened so far.

January 1 → May 9, 2026. The pipeline view. Most stage-level metrics are TBD until HubSpot Sales module is live and stage-to-system mapping is complete.

1
Active Deals
In market today
$26M
Weighted Pipeline
Source: deck v3 · Mar 30
~3,471
Pre-TIA Contacts
9 segments · deployed
TBD
TIA Booth Visitors
Apr 15–16 count pending
TBD
Avg Time to Close
Need historical data
Open Item · CRM Migration

Deal-stage data currently lives in Mike's homegrown CRM. HubSpot Sales Hub build is in flight (Ciara, Spoke Marketing). Stage-to-system mapping call (Mike + Ciara + Dan) is on the schedule. Until that mapping is locked, stage-by-stage scoreboard rows on this page will read TBD.

The Scoreboard

Annual targets vs. status.

Updated bi-weekly · Tuesday cadence. Watch metrics highlighted in ember.

Closed Deals
/ TBD 2026
2026 target not yet set · 12/yr is the 3-year mark
Annual Revenue
/ $10M+ (3-yr)
2026 milestone target TBD
Avg Deal Size
$26M / $40M
Single-deal sample · 1 active in pipeline
LOIs Signed
/ ~13/yr
Implied by 12 closes at 90% close rate
By Lead Source · Pipeline Origin Source: deck v3 · stage tagging needed in HubSpot
TIA-sourced
TBD
COI referral
0 · Q3
Mike's network
TBD
Inbound (Buyers · Portal)
0 · Q4
Daily Operating Dashboards · Mike's System

What Mike opens every morning.

The Scoreboard above is the leadership view (bi-weekly). Below are the daily operating dashboards Mike actually runs against to keep deals moving. Each is a named artifact in his proprietary system today; each needs a HubSpot equivalent before Mike's full migration lands.

CRM Calls Due

Daily list of every CRM record with a follow-up action expected today or overdue. Mike opens this every morning. Drives the day's outreach without him having to remember who's owed a touch.

Data Room Access Due

Buyers granted data room access who haven't moved within 10 working days. Triggers a check-in email so they don't go silent at the most fragile point in the deal.

LOI Expected

Buyers post-management-presentation with an LOI commitment date. Surfaces overdue ones for a nudge before the deal goes cold (referenced as Play step 01 in Stage 08 LOI).

Portal Renewals

Customer Portal subscribers approaching annual renewal. Mike reaches out 30 days before expiry. Able Transfer flagged on the May 12 call as needing renewal outreach.

The existing content above is what is. The closing section is the conversation: how to formalize the operating system relationship from here.

Section 7
The leadership conversation

What's open.

The Operating System is the leadership team's question to itself: how much of the Bloom Growth OS does Next Mile formally adopt? The team is using the Meetings essential well. The other 7 essentials are either implicit (in pieces, across other documents) or absent. This section frames the choice rather than makes it.

O&O #36 · referenced in next tab

Operating System Adoption — scope and sequencing.

Working title for the next-Tuesday agenda item: "Bloom Growth OS — formal scope and sequencing decision." Three paths visible from where Next Mile sits today:

Path A
Engage a Bloom Growth coach

Sign up for the full Bloom Day 1 facilitation and the 2-year journey (Day 1 · Day 30 · Day 60 · Day 90 · quarterly thereafter). Highest investment, highest fidelity. The 8 Essentials get scored properly, the Growth Plan gets built, the team experiences the Deeper Bond exercise, the operating cadence becomes formal.

Path B
Self-implement the framework

Use the Bloom Day 1 Facilitation Guide directly — already in the firm's possession — and run the leadership team through it internally. Lower investment, requires Dan or another team member to facilitate. Useful if the team wants the framework but not the coaching relationship.

Path C
Selective extraction

Keep the Meetings essential (Bloom Weekly) which is already working. Pull in the 1-Year Goal Cascade and Quarterly Priorities work via the existing leadership cadence (O&O #7). Don't formally adopt the rest. This is the lowest-cost path; it's also what the firm is implicitly doing today.

Pre-existing context: Some elements of the playbook already use Bloom terminology — the calibration handoff document referenced "the Bloom 3D process" by name. The team's mental model has Bloom Growth in it; what's not yet resolved is whether the firm names it explicitly, scopes it deliberately, and decides how much of it lives at the firm vs. only in the leadership team's working language.

Department · The Playbook

The Playbook.

For the sales force. 11 stages from first contact to alumni referral. Three audiences moving through one engine.

Stage Plays

The marketing and sales actions that move a record from one stage to the next. Every Spread carries a numbered, audience-tagged play list.

Audience Paths

Three audiences move through the same 11 stages: Sellers, COIs, Buyers. Pace and messaging diverge; pipeline structure is shared.

Master Flow · Sellers Play

The journey, all at once.

Every Next Mile seller deal traverses these 11 stages. Most flow straight through; some branch into the Portal (when the seller is real but the numbers aren't); all close stages eventually feed the Referral Engine, which loops back to fresh Engagement. This is the master view. Click any stage to drill in.

Phases · color key
Awareness · the seller recognizes the moment Consideration · evaluating fit, honest valuation Decision · prep, market, negotiate, close Customer · post-close transition · 90-day handoff Retention · alumni · the referral engine Portal · the off-ramp when not yet ready
Awareness Stage 01
Consideration Stages 02 – 04
Decision Stages 05 – 09
Customer Stage 10
Retention Stage 11
Off-ramp · Portal

The "not yet, not no" path.

From Stage 04 Evaluation, sellers who are real fits but whose numbers aren't right yet route to the Portal — a paid subscription where Mike's TMS data pull translates their operating data into KPIs a buyer wants to see. They get nurtured back toward readiness; when the metrics align, they re-enter the pipeline at Stage 04 or Stage 05.

Branch trigger: Stage 04 evaluation surfaces real fit but wrong timing or wrong multiple → enter Portal subscription
Loop · Alumni

The engine that refills itself.

Stage 11 doesn't end the play — it restarts it. Closed sellers become alumni who introduce new sellers, write case studies, and provide voice-of-customer material. Each new introduction enters at Stage 02 Engagement with the highest-quality warm context Next Mile gets.

Loop trigger: Stage 11 alumni introduces a peer → record enters Stage 02 Engagement with COI-referral context
How to read this · three lenses
For Wally and Mike · pre-call

Where is this deal? Click the stage. Read the cockpit — Flow, Mindset, Assets, Checklist — before the call. The Master Flow is your "you are here" before you drill in.

For Ciara · HubSpot build

The rail is the pipeline. Phases are deal-stage groupings. Portal is its own pipeline that intersects at Stage 04. Alumni loop is a workflow rule, not a stage; Stage 11 advances reset to Stage 02.

For Dan and John · coaching

Where do deals stall? Where does the messaging break? The Master Flow is the bi-weekly leadership orientation — narrate this in 90 seconds before drilling into the stages that are working or stuck.

The decisions that move a seller

The Seller's Path.

A process map of a single seller's journey through the Next Mile engine — every action, every decision, every branch. Master Flow above shows the journey shape; Stages below shows operational depth at each step; this view shows the decision logic that connects them. The mid-resolution chart and decision table below are designed to be the source-of-truth for HubSpot workflow design when Ciara is mapping branching rules.

Also available as a standalone file for sharing outside this playbook.

How to read this

Shape legend.

Each shape carries a specific meaning. The mid-resolution chart below uses every shape; the stage-level chart uses only the action and decision shapes. The dashed-border style is for off-ramps (Portal, alumni, lost) — paths a seller may take that don't lead to a close on the current attempt.

START / END
Terminal
Entry or exit point of the entire flow. Always at the top or bottom.
Action
Action
A step someone (or HubSpot) takes. Each one is a candidate for a HubSpot workflow node.
Decision?
Decision
A Yes/No branching question. Each becomes a HubSpot branching rule.
Asset
Data / Asset
A record, list, or document the flow reads from or writes to.
Off-ramp
Off-Ramp
Dashed border = the seller leaves the standard close path (Portal, long-tail nurture, lost, alumni loop).
Stage-level summary

The path at a glance.

The 11 stages of the Sellers play plus the three off-ramps that catch sellers who don't follow the standard close path. Read top-to-bottom. Every off-ramp is recoverable — Portal sellers can return to Stage 04 when ready; lost sellers can re-enter at any stage; alumni become referral sources.

START · Source STAGE 01 Prospecting STAGE 02 Engagement STAGE 03 Education STAGE 04 Evaluation OFF-RAMP · LONG-TAIL No response · monthly nurture OFF-RAMP · PORTAL Population A · numbers not yet ready STAGE 05 Preparation STAGE 06 Market Engagement STAGE 07 Connected STAGES 08–09 LOI · Diligence OFF-RAMP · LOST Re-enterable · record reason STAGE 10 Transition · Close STAGE 11 · ALUMNI LOOP ALUMNI INTRO LOOP no response numbers not yet deal lost
Mid-resolution · operational detail

Every decision, mapped.

The full operational flow. Every action a seller, Wally, Mike, or Marketing takes. Every decision point that branches the path. Every off-ramp. Designed so that each decision diamond becomes a HubSpot branching rule and each action rectangle becomes a workflow node or lifecycle-stage transition.

START Named-account list cold list · TIA · referral · alumni · inbound STAGE 01 · PROSPECTING Cold Outbound · 4-wk cadence Responded within 30 days? OFF-RAMP Long-tail nurture · monthly No re-trigger Yes STAGE 02 · ENGAGEMENT 15-min fit call · diagnostic Selling on their mind in next 24 months? OFF-RAMP · LONG-TAIL Monthly content · 24+ months out No Yes STAGE 03 · EDUCATION John's library · quarterly check-in Numbers ready for target multiple? OFF-RAMP · PORTAL Population A · improve multiple No when ready Yes STAGE 04 · EVALUATION Numbers review · multiple math Engagement letter signed? REVERT · STAGE 03 More education · or lost No Yes STAGE 05 · PREPARATION CIM · teaser · buyer list CIM + Teaser produced stored in HubSpot library STAGE 06 · MARKET ENGAGE Buyers contacted · NDA signed Qualified buyer interest secured? REVISIT · STAGE 05/06 Reposition · or pause deal No Yes STAGE 07 · CONNECTED Buyer meetings · Q&A · refine LOI received and accepted? REVERT · STAGE 06/07 Continue outreach · or pause No Yes STAGES 08–09 LOI signed · Diligence Deal closes at LOI terms? LOST Record reason · re-enterable No Yes STAGE 10 · CLOSE Wire received · success fee paid STAGE 11 · ALUMNI LOOP ALUMNI INTRO LOOP · feeds Stage 01
For Ciara · HubSpot mapping reference

Decision reference.

Every diamond in the mid-resolution chart, listed here with its input signals and its branch outcomes. Each row is a candidate for a HubSpot workflow branching rule. The Input column tells you what HubSpot property or signal triggers evaluation; the Yes/No columns tell you what stage transition or workflow each branch produces.

No. Question Input signal Yes branch No branch
D1 Responded within 30 days? Any reply, form fill, calendar booking, email click + LinkedIn accept within 30 days of first touch. HubSpot Lead Status field flips from "Cold" to "Engaged." YesAdvance to Stage 02 Engagement. Wally schedules 15-min fit call. NoMove to Long-Tail Nurture list. Monthly content cadence. Re-evaluate quarterly.
D2 Selling on their mind in next 24 months? Direct language from the 15-min fit call. Mike or Wally tags Contact field "Exit Horizon" with one of: <12 mo · 12-24 mo · 24-60 mo · No. YesAdvance to Stage 03 Education. John's library deployed. NoMove to Long-Tail Nurture (24+ months). Monthly content. Re-evaluate annually.
D3 Numbers ready for target multiple? Self-assessment + portal review. Indicators: revenue trend, customer concentration, EBITDA quality, growth profile. Mike or analyst tags "Multiple Readiness" as Ready / Not Yet. YesAdvance to Stage 04 Evaluation. Engagement letter conversation begins. NoOff-ramp to Portal (Population A). Monthly TMS + financials cadence. Return to Stage 04 when ready.
D4 Engagement letter signed? Signed engagement letter received. HubSpot Deal Stage advances to "Prepare." Marks transition from prospect to committed seller. YesAdvance to Stage 05 Preparation. CIM, teaser, buyer list production begins. NoRevert to Stage 03 Education for more nurture, or mark Lost if a hard "no, going elsewhere."
D5 Qualified buyer interest secured? Number of NDA-signed buyers reviewing the teaser. Threshold typically 3-5 qualified for a competitive process. Mike confirms qualification. YesAdvance to Stage 07 Connected. Schedule buyer meetings. NoRevisit Stage 05/06: reposition CIM, refresh buyer list, or pause the deal entirely.
D6 LOI received and accepted? Letter of Intent received from at least one buyer with terms within seller's acceptable range. Mike confirms terms; seller signs LOI. YesAdvance to Stages 08-09. LOI signed, exclusivity begins, diligence starts. NoRevert to continued buyer outreach (Stage 06/07) or pause deal pending new buyer cohort.
D7 Deal closes at LOI terms? Diligence complete, purchase agreement signed, wire received. Deal advances to "Closed Won" in HubSpot. YesAdvance to Stage 10 Transition. Success fee paid. Seller enters Stage 11 Alumni Loop. NoMark Lost. Record loss reason (price, terms, walk-away, diligence finding). Contact remains re-enterable.
Stage 01 · Sellers Play

Prospecting.

The first touch
Run the plays. Outbound from the named-account lists. Three parallel paths share infrastructure but diverge on scripts and CTAs: Sellers, COIs, and Buyers.
Owner · Lead routing by Contact Type · Sellers/COIs → Wally · Buyers → Mike
Exit · Form submission · phone call · direct reply → advance to 02 Engagement
CRM Stage · HubSpot Sales Hub · Contacted
Jump to
01 · The Flow

How a deal moves through Prospecting..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Run the plays. Outbound from the named-account lists. Three parallel paths share infrastructure but diverge on scripts and CTAs: Sellers, CO…
Exit trigger
Form submission · phone call · direct reply
Advance
advance to 02 Engagement
Step
Trigger
Advance
02 · Mindset

Where they're at.

"Another M&A firm is reaching out. I get these every week. Are they actually different, or is this just another smile-and-dial?"
What they're doing

Running their business. Bumping into pressure they may not have fully named: a partner mentioning retirement, an insurance renewal that came in higher than expected, a customer concentration question from their CPA. Not searching. Not in a buying process. Just living with it.

Who they're talking to

No one yet, formally. Maybe a peer at a conference. Maybe their spouse. Maybe an insurance broker (First-to-Know COI) who's seeing the same risk patterns.

What they need to see / feel

Something that doesn't look like the last twelve M&A pitches. Industry credibility on the sender. Specific to their world (T&L, freight brokerage, asset-based trucking) — not generic "we sell businesses." A reason this email is different from the rest.

What kills the move

Corporate-speak. A name they don't recognize from the industry. A pitch in the first paragraph. Generic LinkedIn template language. Anything that signals "salesperson," not "operator who gets it."

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
All
Named account lists · curated, tagged, owner-assigned
The upstream artifact every other step depends on. Sellers (Cold Targeted, Engaged Early through Engaged Ready), COIs (Tier 1 through 5), Buyers (Known Database, Met at TIA). Tagged in HubSpot with contact type and play. Owner assigned per record.
In Progress TBD
Sellers
"Get a Free Confidential Assessment" landing page
The seller-side conversion asset. A clean page with the assessment offer, expectation setting, and a low-friction intake form. The page address every Seller outbound touch points to.
In Progress TBD
COIs
"Schedule a Confidential Conversation" landing page
The COI-side conversion asset. Same architecture as the seller page, different framing: partnership conversation, not a pitch. Drives toward a 20-min structured intro.
In Progress TBD
Buyers
"Selective Buyer Network" landing page
The buyer-side conversion asset. Different intent: buyers self-identify by completing a profile to be considered for fit on future deals. Lower priority today (Phase 3 play), but the page needs to exist when the Buyers play activates.
In Progress TBD
All
Form-submission auto-response sequence
Immediate email when a form submits on any of the three landing pages. Confirms receipt, sets the SLA expectation (sales follows up within 24 hours), routes the record to the right owner.
In Progress TBD
All
Lead routing rules · form → Contact Type → Owner assignment
The HubSpot configuration that makes Wally and Mike see the right records in their dashboards. Sellers and COIs default to Wally. Buyers default to Mike. Override per record as needed. Triggers an owner task within 24 hours of submission.
In Progress TBD
All
9-segment HubSpot email sequences (TIA · proof of concept)
The pre-show, at-show, and post-show waves built for TIA. Each segment matched to its source list. Live and running — the proof point that this infrastructure works.
Have TBD
Sellers
Multi-touch outreach cadence · Sellers · email + LinkedIn + phone
The 4-week sequenced play that goes against the Cold Targeted seller list. Diversified channels protect against any single one failing. Built from the TIA segment templates.
In Progress TBD
COIs
Multi-touch outreach cadence · COIs · email + LinkedIn
The COI-specific cadence. Different framing (peer-to-peer, partnership), different rhythm (longer between touches), same diversified-channel principle.
In Progress TBD
All
Monthly educational email · market trends & deal stories
Keeps Next Mile in the inbox between active touches. Real value, not promotional. Engagement signals (opens, clicks, replies) re-surface dormant prospects to Wally's queue.
In Progress TBD
All
"Break-up" email · final touch after 3+ attempts
The dignified close after multiple no-replies. Either re-opens the relationship or clears the contact from active follow-up so the funnel stays clean.
In Progress TBD
All
Programmatic digital · LinkedIn + Google retargeting
Always-on awareness layer for prospects who've visited but haven't converted. Deferred until the Buyers play activates and demand warrants the spend.
In Progress TBD
Sellers
Cold outreach script · Sellers · "operator who gets it" opener
The opening copy when reaching out cold to a named seller. Industry credibility first (Wally's operator background, Mike's Echo/Yellow history), partnership framing, no pitch.
In Progress Lead routing by Contact Type · Sellers/COIs → Wally · Buyers → Mike
COIs
Cold outreach script · COIs · the 30-second conversation
The repeatable opener for COIs, documented in the COIs tab. "We work with brokerage owners who are preparing for growth or an eventual exit, usually 2 to 5 years out..." Earns the 20-minute follow-up.
In Progress Lead routing by Contact Type · Sellers/COIs → Wally · Buyers → Mike
All
LinkedIn DM script · value-first, no ask on first touch
The opening DM that earns the right to a second message. No meeting ask on touch one. Audience-specific opener but shared structure.
In Progress Lead routing by Contact Type · Sellers/COIs → Wally · Buyers → Mike
COIs
COI warm intro script · leverage mutual relationship
When a COI offers an introduction. The message that travels through the COI's channel to the prospect, framed so the COI looks good making the intro.
In Progress Lead routing by Contact Type · Sellers/COIs → Wally · Buyers → Mike
All
Objection-handling matrix · top brush-offs with response by play
A live document of the most common brush-offs and the responses that re-open the conversation. Updated weekly as new patterns surface from active outreach.
In Progress Lead routing by Contact Type · Sellers/COIs → Wally · Buyers → Mike
1 Have
16 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Prospecting., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: Form submission · phone call · direct reply. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: advance to 02 Engagement
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 01
CompanyContactNoteRep
Post-TIA · Sellers cohort 12 contacts (TBD) Wally
Post-TIA · Buyers cohort 6 contacts (TBD) Mike
Post-TIA · COIs cohort 35 contacts (TBD) Wally
Dashboard · Live in HubSpot
Outbound touches
Connection rate
Form submissions
Meetings booked
Plays that feed this stage

Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 01's Stage Play actually addresses what the prospect is experiencing.

  • "What they need to see": industry credibility, T&L-specific framing, no pitch in paragraph one. → Served by steps 13 (Sellers script · operator opener) and 14 (COIs · 30-second conversation), both anchored in Wally and Mike's industry resume. The cold outreach copy needs to lead with operator credibility, not Next Mile credentials.
  • "Who they're talking to": peers and First-to-Know COIs (Tier 1) hear the early signals first. → Served by step 09 (Multi-touch cadence · COIs) and the COI play running in parallel. The COI flywheel is the validation engine that makes Seller cold outreach warmer when it lands.
  • "What kills the move": generic template language, corporate-speak, name they don't recognize. → Served by step 17 (Objection-handling matrix · live doc updated weekly) catching brush-offs early and step 01 (Named account lists tagged by play) preventing wrong-audience sends. The risk is the multi-touch cadence templates (08, 09) reading generic if not refined against real prospect responses.
Use this when

Onboarding Wally or a future sales hire to Stage 01. Reviewing a draft cold outreach script before it ships. Briefing John on Exit Readiness Library content that supports this stage. Pressure-testing whether a new play step earns its place in the sequence.

Stage 02 · Sellers Play

Engagement.

Worth 15 minutes?
Handle what came in. Convert interest into a real conversation. The 15-minute fit call that confirms interest is real and routes them into the right next stage.
Owner · Wally / Mike
Exit · 15-min fit call complete → Stage 04
CRM · HubSpot · Engaged
Jump to
01 · The Flow

How a deal moves through Engagement.

From inbound signal to one of two outcomes. Ciara builds the HubSpot pipeline against this; Wally keeps it in his head before every fit call.

Trigger · In
Inbound signal: form, phone, direct reply, or COI referral
Action · Owner
Auto-task to Wally or Mike · 24-hr SLA · Soft Ask reply
Touch
15-min fit call · diagnostic, not pitch
Decision
Interest real? Timing right?
Advance · Ready
Discovery booked → Stage 04 Evaluation
or
Recycle · Not yet
Real fit, wrong timing → Stage 03 Education (nurture)
Step
Decision
Advance
Recycle
02 · Mindset

Where they're at.

"Okay, I'll give them 15 minutes. If they pitch valuation in the first three minutes, I'm out."
What they're doing

Showing up to an intro call with low trust and high skepticism. Looking up Mike or Wally on LinkedIn beforehand. Quietly evaluating whether this is worth their time.

Who they're talking to

Themselves. Not telling anyone yet. Maybe casually asking a trusted peer if they've heard the name.

What they need to see / feel

That Mike or Wally actually listens. That the conversation is a diagnostic, not a presentation. That whoever's across from them knows LTL, asset-based trucking, broker margins, the way the industry actually works. Wally's operator background does heavy lifting here.

What kills the move

Talking about Next Mile's process before asking about their business. Quoting fees in the first call. Treating it like a transaction. Sounding like a banker.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
WordPress site · WhatConverts call tracking
Credibility foundation. Inbound calls logged for source attribution.
nextmilema.com · WhatConverts dashboard
Have Beanstalk · Natalie
Meeting request form (replaces direct calendar)
Captures intent before booking. Auto-routes to owner.
nextmilema.com · HubSpot routing pending
Have Beanstalk · Ciara
Send to CRM workflow
Marketing DB → Sales pipeline conversion. HubSpot equivalent: deal-creation workflow on Contact Type change.
Mike's CRM · HubSpot rebuild in Phase 2
Have Mike · Ciara
Referral email handling · COI intros
COI emails become HubSpot records automatically rather than living in Mike's inbox.
HubSpot forwarding alias · spec pending
In Progress Ciara
"Soft Ask" script — "Open to a brief chat?"
Opening line when a prospect responds to a touch. Low-commitment, owner-language, no pitch.
Drive · HubSpot integration folder
In Progress John · Natalie
Voicemail script — 20-sec curiosity hook
For when the callback doesn't connect. Curiosity over pitch.
Drive · HubSpot integration folder
In Progress John · Wally / Mike
Initial fit qualification call script · 15-min
Diagnostic-led, not qualification-led. Confirms interest is real before booking discovery.
To be drafted · HubSpot Playbook
Need Dan + John
Discovery booking flow → Stage 03 or 04
Captures readiness signals (timeline, valuation expectations, partner alignment).
HubSpot scheduling link · custom form fields
Need Ciara · John
COI deeper-dive agenda
Second COI conversation — moves "interesting" to "let's structure a referral relationship."
To be drafted
Need Dan + John
Fit-call follow-up · "no" path template
When the fit call surfaces it isn't right. Closes professionally, protects the community footprint.
HubSpot email template library
Need Natalie · John
Fit-call follow-up · "yes / book discovery"
Confirms next step, includes discovery booking link, sets Stage 04 expectations.
HubSpot email template library
Need Natalie · John
3 Have
3 In Progress
5 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · 20 min prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Engagement, owner = you, lead source captured.
  • Re-read the Mindset (left column). Low trust, high skepticism. Diagnostic, not presentation. Don't quote fees.
  • Look up the company. Mode (asset-based, brokerage, 3PL, LTL), revenue band, ownership history. Use ZoomInfo data if in the record; LinkedIn for the owner.
  • Look up the person. LinkedIn — tenure, prior role, life-cycle signals (acquired before, second-time founder, near retirement).
  • Check inbound origin. Form? Phone (WhatConverts)? COI referral? Campaign reply? The origin sets your opening line.
  • Have the Soft Ask script open in another tab so the opening 60 seconds is reflexive, not improvised.
During · 15 min on the call
Diagnostic, not pitch.
  • Open with what they sent / said. Reference their actual signal — the form question, the voicemail, the COI's intro. Shows you read it.
  • Ask what changed recently. Not "are you thinking of selling" — that's a pitch. The Pressure Test prompt: "what's changed for you recently."
  • Listen for the real motivation. Operator fatigue, partner misalignment, an offer they're shopping, a health event, tax deadline. Stated reason rarely matches the real one.
  • Establish industry credibility in 3 minutes. Use their language — broker margins, asset-based fleets, LTL, contract vs. spot. Wally's operator background does heavy lifting.
  • Do NOT quote fees, walk through Next Mile's process, or pitch the portal. "Let's talk about whether this is the right move first; fees come after fit."
  • Close with one of two next steps: book 60-90 min discovery (Stage 04), or schedule 30/60/90-day check-in (Stage 03 nurture).
Field validation pending These items reflect Mindset + Pressure Test language. The specific question sequence will tighten after Mike's 18 recorded calls are analyzed against this stage.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot. What they said, what you heard underneath it, the real motivation. Two or three sentences — but write it before the next call wipes it out.
  • Update deal stage based on outcome: Ready → Stage 04 Evaluation. Real fit, wrong timing → Stage 03 Education. Not a fit → Closed-lost with reason code.
  • Send the follow-up email from the matching HubSpot template (yes-path or no-path). Don't free-form it.
  • If advancing to Stage 04: send discovery booking link, set expectations for the 60-90 min session, add prep tasks to the deal record.
  • If recycling to Stage 03: set next-touch task with a specific date and reason. "30-day check-in re: equipment refinancing" beats "follow up."
  • If a COI was involved: send the COI a status update within 24 hours. They referred — they deserve to know what happened.
  • Flag for call review. New objection? New motivation? Language that landed unusually well? Note it for the bi-weekly review.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue. This is the loop that closes the playbook — what we hear in the field rewrites the script.
Who's Here · Live CRM · Stage 02
CompanyContactNoteRep
Boost Transport Justin (part owner) Atlanta brokerage · 3PL Wally · Mike
Xtreme Travis Add-back / equipment discussion Wally
Tim Quirk (via Mark Drabe) TBD Boston seller · referral fee in play Wally
Donald McDonald 2 referrals incoming Former employee → COI bridge Wally
Boston seller (Mike prior contact) On ice 14 opens · no response Wally
Dashboard · Live in HubSpot
Inbound handled
First-response time
Fit-call show rate
Advance to discovery
Plays that feed this stage

Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 02's execution actually addresses what the prospect is experiencing.

  • "Diagnostic, not a presentation": Mike or Wally listens before pitching. → Served by the 15-min fit call structured as discovery, not qualification interview. The risk is the call defaulting to qualifying questions ("what's your revenue, what's your EBITDA") instead of curiosity-led ("what's changed for you recently").
  • "Knows LTL, asset-based trucking, broker margins": Industry credibility lands in the first three minutes. → Served by Wally as the primary on Sellers and COIs (operator credibility). The risk is a future sales hire not having the same industry vocabulary; the script needs prompts that allow operator-language to surface naturally.
  • "Quoting fees in the first call": Kills trust. → Served by the Soft Ask script and the fit call design itself. Risk: an over-eager response to a pricing question. Mike's answer should always be "let's talk about whether this is the right move first; fees come after fit."
Use this stage when

Coaching a fit-call. Reviewing the inbound routing protocol with Ciara during Phase 2 Build. Onboarding a new sales hire to the inbound-handling motion. Pressure-testing whether a script change still serves the buyer's skepticism.

Stage 03 · Sellers Play

Education.

Not ready, but curious
Stay close to "not-yet" prospects without being annoying. Build the conditions that turn a 2-to-5-year prospect into a Stage 04 conversation when they're actually ready.
Owner · Marketing automation owns cadence · Wally quarterly check-in
Exit · Self-assessment threshold reached · re-engagement signal → advance to 04 Evaluation
CRM Stage · HubSpot Marketing Pro · Educate nurture · Operationally, this stage IS the Portal holding pattern for Engaged-Not-Ready sellers (Vache today; Sutton Envoy for 18+ months).
Jump to
01 · The Flow

How a deal moves through Education..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Stay close to "not-yet" prospects without being annoying. Build the conditions that turn a 2-to-5-year prospect into a Stage 04 conversation…
Exit trigger
Self-assessment threshold reached · re-engagement signal
Advance
advance to 04 Evaluation
Step
Trigger
Advance
02 · Mindset

Where they're at.

"I know I want to sell eventually, but the numbers aren't where I need them to be. I'm not sure what to do next — or if anyone can actually help me get there without just telling me to wait."
What they're doing

Reading market insights when they land. Filling out the "Are You Ready?" self-assessment. Maybe attending a webinar. Engaging with the Portal Growth Program if they signed up. Holding off on conversations but staying in the orbit.

Who they're talking to

Their CFO or controller (if they have one). Their CPA. Sometimes a business partner. The phrase "in a couple of years" comes up a lot.

What they need to see / feel

Content that names the gap honestly: here's where you are, here's what would change the valuation, here's how long it typically takes. A coach, not a salesperson. Confidence that Next Mile will still be there when they're ready.

What kills the move

Disappearing for six months after the first call. Repeated "are you ready yet?" follow-ups. Pressure tactics. Treating their not-yet as a no.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
Portal onboarding sequence · welcome + monthly check-in
The automated welcome and monthly nurture for prospects who enroll in the Portal Growth Program. Keeps them in the ecosystem without manual outreach.
In Progress TBD
"Are You Ready?" landing page · self-assessment
The decision-point asset. Prospects answer a short series of questions and get scored. Hot scores flag back to Mike for re-engagement; cooler scores stay in nurture.
In Progress TBD
Market insights series · "What is my T&L business worth?"
The lead magnet. Answers the question every owner wants answered but won't ask in person. Builds authority before any pitch.
In Progress TBD
Webinar: "The Next Mile Process" · gated
Gated registration captures intent signal. Prospects who attend self-select as "considering selling within the next 12-24 months."
In Progress TBD
Anonymized case studies · 1-page PDF leave-behind
One-pager that fits a follow-up email or a coffee meeting. Real deals, anonymized, with the outcome owners care about.
In Progress TBD
Quarterly "Stay Connected" check-in
A real human note quarterly. No automation can substitute for Mike's name in the inbox four times a year.
In Progress Marketing automation owns cadence · Wally quarterly check-in
Value-gap coaching call · what to work on to hit target EBITDA
A working call with Mike when a prospect is too small now but trending up. Names what they would need to change to be ready.
In Progress Marketing automation owns cadence · Wally quarterly check-in
90-day re-engagement script
When the portal engagement signals go quiet. A short, low-pressure check-in that re-opens the conversation without restarting it.
In Progress Marketing automation owns cadence · Wally quarterly check-in
COI referral follow-up script
When a COI referred someone and we need to keep the COI informed of progress without breaching prospect confidentiality.
In Progress Marketing automation owns cadence · Wally quarterly check-in
0 Have
9 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Education., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: Self-assessment threshold reached · re-engagement signal. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: advance to 04 Evaluation
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 03
CompanyContactNoteRep
Vache TBD First Portal subscriber · $500/mo · 1-yr min Mike
Chad Caldwell Wally's contact $7M rev · $1.5M profit · LOI under review Mike
Dashboard · Live in HubSpot
Portal active users
Quarterly check-in completion
Webinar attendance
Re-engagement rate from nurture → Stage 04
Plays that feed this stage

Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 03's Stage Play actually addresses what the prospect is experiencing.

  • "Names the gap honestly": Content that says "you're here, you'd need to be there, this is how long" without sugar-coating. → Served by step 07 (Value-gap coaching call) and the "Are You Ready?" self-assessment. Risk: the assessment that flatters everyone is worse than no assessment.
  • "A coach, not a salesperson": The Portal Growth Program ($500/mo) is structured as ongoing coaching. → Served by step 01 (Portal sequence) and step 07 (coaching call). Risk: the monthly portal content reading promotional instead of substantive.
  • "Disappearing for six months": Kills the relationship. → Served by the quarterly check-in (step 06) and the monthly portal touch (step 01). The discipline is the cadence; the failure mode is letting Mike's "I'll get to it" become a six-month gap.
Use this when

Briefing John on Exit Readiness Library content production (this is where most of his content lands). Designing the Portal Growth Program experience. Reviewing whether monthly nurture is hitting the right note or has gone generic.

Stage 04 · Sellers Play

Evaluation.

The reality check
Honest valuation + Go/No-Go decision. Either advance to engagement, recycle to Education with a plan, or part professionally.
Owner · Mike leads · Wally on cultural/operator questions
Exit · Engagement agreement signed → advance to 05 Preparation
CRM Stage · HubSpot Marketing Pro · Qualified
Jump to
01 · The Flow

How a deal moves through Evaluation..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Honest valuation + Go/No-Go decision. Either advance to engagement, recycle to Education with a plan, or part professionally.
Exit trigger
Engagement agreement signed
Advance
advance to 05 Preparation
Step
Trigger
Advance
02 · Mindset

Where they're at.

"I think I'm ready to sell, but I don't really know what my business is worth. I'm nervous about what the numbers will show — and I'm not sure if anyone will actually want it."
What they're doing

Pulling together three years of financials. Maybe nervously. Wondering if the EBITDA addbacks they've been making are legitimate. Re-reading the engagement agreement before signing.

Who they're talking to

Their CPA more than they have in years. Their spouse — this is the moment it gets real for the family. Sometimes a trusted partner. Almost never employees yet.

What they need to see / feel

An honest valuation, not a flattering one. Mike's straight-shooter posture matters here — they need to hear what's wrong as much as what's right. Confidence that Next Mile won't take a listing they shouldn't take.

What kills the move

An inflated valuation they'll later be embarrassed about. Hiding the deal-killers until they surface in diligence. Pretending issues don't exist.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
Financial intake checklist · 3-yr P&L, balance sheet, returns
The first ask after sign-on. Standardized so nothing gets missed and the seller knows exactly what to send.
In Progress TBD
Red flag scoring sheet · weighted deal-killer criteria
Quantitative gate before we invest more time. Customer concentration, owner dependency, EBITDA quality, tax exposure each scored.
In Progress TBD
Valuation range report template · standard delivery format
How the valuation gets delivered to the seller. Same format every time so the seller can compare to what they have heard elsewhere.
In Progress TBD
Valuation simulation engine · preset EBITDA multiples by size + type · Mike's system
Mike's engine carries preset multiple ranges by company size and type (asset-based vs non-asset, mode mix, geography). When a seller's normalized EBITDA is calculated, the engine runs the simulation against those presets and produces the implied valuation range. This is the math behind the "Valuation range report" — Mike walks the seller through the inputs, not the conclusion. Exists in Mike's proprietary system today.
Have TBD
10-year amortization + IRR + NPV graphics · valuation defense
Once the simulation produces a valuation range, the engine generates the 10-year amortization view with IRR and NPV graphics. This is what makes the valuation defensible — the seller sees the financial logic, not just a number. Used in the Go/No-Go conversation and again in buyer-facing CIM material.
Have TBD
Engagement agreement template · legal review pending
The Go/No-Go output artifact. Pending final legal review before live use.
In Progress TBD
Seller interview guide · "Why are you selling?"
The 60 to 90 minute deep dive that frames the entire engagement. Surfaces the real motivations behind the sale, not just the stated ones.
In Progress Mike leads · Wally on cultural/operator questions
Preliminary valuation delivery script
How Mike walks the seller through the valuation range. Manages expectations on the high end and explains the math behind the low end.
In Progress Mike leads · Wally on cultural/operator questions
Go/No-Go conversation script
The decision moment. Either Next Mile engages, the seller agrees to wait, or both sides walk. No middle ground.
In Progress Mike leads · Wally on cultural/operator questions
Valuation gap bridge · transition to Education without losing them
When the valuation isn't there yet but the seller is trending up. The bridge into Stage 02 Education without it feeling like a rejection.
In Progress Mike leads · Wally on cultural/operator questions
2 Have
8 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Evaluation., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: Engagement agreement signed. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: advance to 05 Preparation
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 04
CompanyContactNoteRep
Active deal · in-market Confidential $26M weighted Mike
Dashboard · Live in HubSpot
Intake completion rate
Days to valuation delivery
Go/No-Go ratio (Go vs return-to-Education)
Plays that feed this stage

Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 04's Stage Play actually addresses what the prospect is experiencing.

  • "Honest valuation, not a flattering one": Inflated numbers kill trust later. → Served by step 02 (Red flag scoring sheet) and step 06 (Preliminary valuation delivery script). The straight-shooter delivery is the differentiator; Mike's posture matters more than the number.
  • "Hear what's wrong as much as what's right": Set expectations on the call where the valuation is delivered. → Served by step 06 (delivery script) and step 05 (Seller interview guide). The interview surfaces the addback questions; the delivery script names them.
  • "Confidence we won't take a listing we shouldn't": Walk-away discipline. → Served by step 07 (Go/No-Go script) and step 08 (Valuation gap bridge). The bridge is the move that preserves the relationship even when "now" isn't right.
Use this when

Preparing for a valuation delivery call. Coaching Wally on the Seller interview (he'll do these as the firm grows). Reviewing the engagement agreement template against the actual seller experience.

Stage 05 · Sellers Play

Preparation.

Tell the story right
Build a market-ready CIM, blind teaser, and curated buyer list. Coach the seller for buyer-facing meetings.
Owner · Mike leads document production · Wally on positioning + coaching
Exit · CIM approved · buyer list curated → advance to 06 Market Engagement
CRM Stage · Mike's CRM → HubSpot Sales Pro · Preparation
Jump to
01 · The Flow

How a deal moves through Preparation..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Build a market-ready CIM, blind teaser, and curated buyer list. Coach the seller for buyer-facing meetings.
Exit trigger
CIM approved · buyer list curated
Advance
advance to 06 Market Engagement
Step
Trigger
Advance
02 · Mindset

Where they're at.

"I've signed the agreement — now what? I want to feel confident we're presenting the business accurately and showing its best side. I'm nervous about what buyers will think when they see the numbers."
What they're doing

Answering a 50-item deep-dive questionnaire. Pulling customer reports, driver lists, equipment schedules. Reviewing CIM drafts. Worrying about the wrong things looking like the wrong things.

Who they're talking to

Mike or Wally weekly. Their CFO heavily. A small inner circle. Still not employees.

What they need to see / feel

That Next Mile is making the story land. The CIM looks professional. The story is honest but framed well. Their weaknesses are addressed, not hidden. They trust the document is something they'd be proud to put in front of buyers.

What kills the move

A CIM that doesn't sound like their business. Boilerplate. Errors. A buyer list that includes companies they'd never sell to.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
CIM template · cover, exec summary, financials, growth thesis
The headline document buyers see. Standardized layout so every CIM has the same elements in the same order.
In Progress TBD
Blind Teaser template · 1-page redacted PDF
The one-pager that goes out to the buyer list. No company name, no employee names, no customer names. Generates response without breaking confidentiality.
In Progress TBD
Deep dive questionnaire · 50+ questions
The input that drives CIM writing. Comprehensive enough that the seller only fills it out once, organized so answers map directly to CIM sections.
In Progress TBD
Buyer list scoring matrix · strategic vs financial
Curation tool. Mike's 300+ buyer database scored against this deal's profile to surface the right targets, not the full list.
In Progress TBD
Expectation-setting script · timeline & confidentiality
The kickoff conversation. Sets the 4 to 6 month timeline, explains who will see what, and addresses the seller's #1 fear: their team finding out.
In Progress Mike leads document production · Wally on positioning + coaching
Positioning conversation · address weaknesses with seller
The honest pre-CIM conversation about what will not look great on paper. Better that Mike says it first than a buyer surfaces it.
In Progress Mike leads document production · Wally on positioning + coaching
CIM review session script · seller approval before market
Mandatory gate. Nothing leaves the room without the seller's eyes on it and explicit sign-off.
In Progress Mike leads document production · Wally on positioning + coaching
Management presentation prep · "Dog & Pony Show" coaching
The rehearsal before Stage 06 management presentations. How to tell the company's story to a room of buyers without sounding scripted.
In Progress Mike leads document production · Wally on positioning + coaching
0 Have
8 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Preparation., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: CIM approved · buyer list curated. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: advance to 06 Market Engagement
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 05
CompanyContactNoteRep
TBD
Dashboard · Live in HubSpot
Days from kickoff to CIM-approved. Buyer list size (curated). Seller satisfaction with CIM
Plays that feed this stage

This stage is internal to the deal lifecycle — no acquisition plays feed it directly. Work in this stage is execution against deals already advanced from prior stages.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 05's Stage Play actually addresses what the prospect is experiencing.

  • "The CIM looks professional · sounds like their business": Boilerplate kills it. → Served by step 03 (Deep dive questionnaire · 50+ questions) which captures the seller's voice, then step 07 (CIM review session) which gates approval. The CIM has to read like the seller wrote it with help, not like Mike wrote it about them.
  • "Weaknesses addressed, not hidden": The honest framing is the differentiator. → Served by step 06 (Positioning conversation) where Mike names what looks ugly before a buyer surfaces it. The discipline: better to lead with the weakness than have it surface in diligence.
  • "A buyer list of companies they'd never sell to": The seller knows their industry. → Served by step 04 (Buyer list scoring matrix) and the curation discipline. The discipline: Mike runs the cut by the seller before going to market, every time.
Use this when

Onboarding a CIM production cycle. Coaching a new analyst on the Deep Dive questionnaire. Reviewing the buyer list against the seller's "would I take their money" gut check.

Stage 06 · Sellers Play

Market Engagement.

It's out there
Curated outreach to the buyer list. Manage NDAs and qualified-buyer access. Keep the seller informed without overwhelming.
Owner · Mike runs buyer outreach · Wally on seller communication cadence
Exit · Qualified buyer · NDA signed · intro Zoom complete → advance to 07 Connected
CRM Stage · Mike's CRM → HubSpot Sales Pro · In-Market
Jump to
01 · The Flow

How a deal moves through Market Engagement..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Curated outreach to the buyer list. Manage NDAs and qualified-buyer access. Keep the seller informed without overwhelming.
Exit trigger
Qualified buyer · NDA signed · intro Zoom complete
Advance
advance to 07 Connected
Step
Trigger
Advance
02 · Mindset

Where they're at.

"The CIM is approved and we're ready. I'm nervous — I don't want my employees, customers, or competitors to find out. But I trust the process. I just need to know what happens next."
What they're doing

Checking in with Mike too often, then trying not to. Watching for signs that someone has heard something. Trying to operate the business normally while a major decision moves behind the scenes.

Who they're talking to

Almost no one. Maybe a partner. The circle of knowledge is the smallest it'll ever be.

What they need to see / feel

Friday updates that explain the silence. Reassurance that confidentiality is holding. Visibility into who's been approached and how they've responded. A sense that Next Mile is running the process, not just waiting.

What kills the move

Going dark for two weeks. A buyer name surfacing in their network unexpectedly. Sloppiness with the blind teaser. Anything that breaks the confidentiality compact.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
Blind Teaser email sequence · 3-touch with open tracking
How the teaser actually reaches buyers. Three touches per buyer, opens and clicks tracked; no responses filter out.
In Progress TBD
NDA template · standardized mutual NDA per pair
The gate between teaser interest and CIM access. Standardized so the legal back-and-forth doesn't slow the funnel.
In Progress TBD
Data room folder structure · access control protocol
What buyers access after signing the NDA. Locked-down structure with read-only protections; sensitive items (customer names, driver lists) gated until later.
In Progress TBD
Data Room Update auto-email · monthly refresh notification · Mike's system
When monthly seller data is posted to the data room, the system auto-emails each granted buyer telling them new data is available and what changed. Buyers stay current without Mike having to ping each one. Pairs with the 10-working-day access expectation — when a buyer goes quiet, the next auto-email is what re-engages them. Mike's existing tool; need to mirror as a HubSpot workflow when CRM moves over.
Have TBD
Intro Zoom agenda · 15-min strategic fit assessment
The first live conversation with a buyer. 15 minutes is the contract: enough to assess fit, not enough to leak sensitive detail.
In Progress TBD
Seller briefing · "Here's what to expect in next 30–60 days"
Set the seller up for the silence that follows go-to-market. Without this, sellers panic when nothing happens for a week.
In Progress Mike runs buyer outreach · Wally on seller communication cadence
Weekly seller update template · teasers, responses, NDAs
The Friday recap. Standard format so Mike isn't writing custom updates and the seller knows when to expect them.
In Progress Mike runs buyer outreach · Wally on seller communication cadence
Intro Zoom qualification script · strategic fit filter
How Mike runs the 15-minute intro call. Filters tire-kickers from serious buyers before either side invests further time.
In Progress Mike runs buyer outreach · Wally on seller communication cadence
Q&A management · objections without revealing sensitive info
Real-time skill for handling buyer questions that go too deep too fast. How to deflect without seeming evasive.
In Progress Mike runs buyer outreach · Wally on seller communication cadence
1 Have
8 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Market Engagement., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: Qualified buyer · NDA signed · intro Zoom complete. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: advance to 07 Connected
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 06
CompanyContactNoteRep
TBD
Dashboard · Live in HubSpot
Teasers sent
Open rate
NDAs signed
Intro Zoom show rate
Buyer drop-off by stage
Plays that feed this stage

Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 06's Stage Play actually addresses what the prospect is experiencing.

  • "Friday updates that explain the silence": Without them, sellers spiral. → Served by step 06 (Weekly seller update template). The discipline is the consistency, not the content. A boring Friday update sent every week beats a great one sent every three weeks.
  • "Confidentiality holding": The single thing that kills a deal at this stage. → Served by step 02 (NDA template) and step 03 (Data room access control). The discipline: sensitive items (customer names, driver lists) gated behind milestone-based unlocks, not bundled in the initial data room.
  • "Running the process, not just waiting": Visibility into outreach matters more than buyer responses. → Served by step 06 (Weekly update) which shows the activity log, not just the outcomes. The discipline: report what was done this week, even if nothing was returned.
Use this when

Standing up the data room on a new deal. Drafting the first Friday update for a seller new to the process. Reviewing whether buyer outreach cadence is respecting the seller's confidentiality boundaries.

Stage 07 · Sellers Play

Connected.

Meeting the buyers
Management presentations completed with multiple qualified buyers. Indications of Interest (IOIs) requested. Position for LOI stage.
Owner · Mike runs buyer meetings · Wally coaches cultural-fit evaluation
Exit · Multiple IOIs received · field narrowed → advance to 08 LOI
CRM Stage · Mike's CRM → HubSpot Sales Pro · Buyer Connected
Jump to
01 · The Flow

How a deal moves through Connected..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Management presentations completed with multiple qualified buyers. Indications of Interest (IOIs) requested. Position for LOI stage.
Exit trigger
Multiple IOIs received · field narrowed
Advance
advance to 08 LOI
Step
Trigger
Advance
02 · Mindset

Where they're at.

"I've met the buyers. Some feel right, some don't. I'm trying to stay objective but it's hard not to get emotionally attached. I need Mike to help me see clearly and not make a decision I'll regret."
What they're doing

Running management presentations. Hosting site visits. Interviewing buyers as much as buyers are interviewing them. Comparing what each buyer said to what their gut said.

Who they're talking to

Buyers, in carefully managed settings. Mike after every meeting. Spouse and partner about cultural fit. Still not employees.

What they need to see / feel

A debrief after every meeting where they can say what they really thought before second-guessing sets in. Coaching on what to weigh: culture, structure, what happens to employees, not just price. Permission to trust their instincts about fit.

What kills the move

Letting the highest-price bidder dominate the conversation. Skipping the debrief. Not asking enough about what happens to their team post-close.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
"Dog and Pony" prep guide · seller coaching
The pre-flight checklist for the seller before facing a room of buyers. Anticipated questions, sharp answers, what to wear, what to bring.
In Progress TBD
Mgmt presentation template · 10-slide format
The deck the seller actually presents. 10 slides keeps the meeting focused and prevents the seller from over-sharing on slide 47.
In Progress TBD
Buyer response tracking sheet · log questions & deadlines
Who asked what, what we owe back, when. Critical for managing multiple parallel buyer conversations without losing thread.
In Progress TBD
Buyer deadline tracker · auto-alert at 5 days no response
Buyers go silent. The 5-day alert prompts Mike to nudge before silence becomes drift.
In Progress TBD
Timeline expectation script · prevents seller anxiety during silence
Used at the start of every week. Reminds the seller that silence between meetings is normal and how the buyer's process moves.
In Progress Mike runs buyer meetings · Wally coaches cultural-fit evaluation
Post-meeting debrief · "How did that feel?"
The 15-minute call after every buyer meeting. Captures the seller's gut reaction while it's fresh and before second-guessing sets in.
In Progress Mike runs buyer meetings · Wally coaches cultural-fit evaluation
"How to evaluate a buyer" coaching · culture, structure, earnout, employees
Sellers default to highest-price thinking. This coaching reframes the decision around culture fit, deal structure, and what happens to their people.
In Progress Mike runs buyer meetings · Wally coaches cultural-fit evaluation
IOI request script · prompt buyers post-management presentation
How Mike asks buyers to put a number on paper without making them feel rushed. The transition from interest to indication.
In Progress Mike runs buyer meetings · Wally coaches cultural-fit evaluation
0 Have
8 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Connected., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: Multiple IOIs received · field narrowed. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: advance to 08 LOI
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 07
CompanyContactNoteRep
TBD
Dashboard · Live in HubSpot
Management presentations held
IOIs received
Buyer drop-off post-presentation
Seller cultural-fit signals captured
Plays that feed this stage

Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 07's Stage Play actually addresses what the prospect is experiencing.

  • "Debrief before second-guessing sets in": Gut reactions captured fresh are different from gut reactions remembered. → Served by step 06 (Post-meeting debrief · "How did that feel?"). The discipline: 15 minutes after every buyer meeting, no exceptions. Mike doesn't let the day end without the debrief.
  • "Coaching on culture, structure, what happens to employees": Sellers default to price thinking. → Served by step 07 (How to evaluate a buyer · coaching). The coaching has to be repeated; one conversation doesn't override decades of "highest number wins" instinct.
  • "Permission to trust instincts about fit": The seller's gut about a buyer is data. → Served by step 06 (debrief) which names the gut feeling out loud. The risk: dismissing a seller's "something's off" as emotion. Mike's job: take the signal seriously and probe it.
Use this when

Walking a seller through their first management presentation. Coaching a future hire on running buyer debriefs. Reviewing whether the buyer list got narrowed for the right reasons.

Stage 08 · Sellers Play

LOI.

Translating the offers
Compare multiple LOIs. Negotiate terms. Sign with the right buyer + sign exclusivity with eyes open.
Owner · Mike leads negotiation · Wally on seller emotional management
Exit · LOI signed · exclusivity executed → advance to 09 Diligence
CRM Stage · Mike's CRM → HubSpot Sales Pro · LOI Active
Jump to
01 · The Flow

How a deal moves through LOI..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Compare multiple LOIs. Negotiate terms. Sign with the right buyer + sign exclusivity with eyes open.
Exit trigger
LOI signed · exclusivity executed
Advance
advance to 09 Diligence
Step
Trigger
Advance
02 · Mindset

Where they're at.

"We have offers. This is real. But I'm overwhelmed by the terms — earnouts, escrow, reps and warranties. I need Mike to translate this and tell me which one is actually the best deal for me."
What they're doing

Reading legal language they don't fully follow. Comparing offers on a kitchen table. Trying to figure out if the highest gross number is actually the best deal. Looking up reps and warranties online.

Who they're talking to

Mike, intensively. Their attorney. Their CPA. Spouse, every night.

What they need to see / feel

The LOIs explained in plain English. A side-by-side that compares what actually matters. Permission to walk away if neither is right. Best Value framing — culture, structure, fit, cash mix — not just headline number.

What kills the move

Walking them through one LOI at a time without comparison. Letting them anchor to the highest headline number. Rushing the exclusivity decision.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
LOI Expected tracking · waiting-state dashboard · Mike's system
After buyers complete the management presentation and signal intent to submit, Mike tags each as "LOI Expected" with a target date. The daily CRM Calls Due dashboard surfaces any that are overdue so they get a nudge before they go cold. This is the silent stretch where deals die — the waiting state needs its own discipline. Mike's existing artifact; should mirror as a HubSpot deal-stage property with date.
Have TBD
Seller "must haves" intake · non-negotiables before LOI review
What the seller will not bend on. Captured up front so when LOIs come in, comparison is easier and emotion stays out of it.
In Progress TBD
LOI comparison matrix · side-by-side terms
Multiple LOIs in one view. Price, structure, earnout, escrow, reps and warranties, exclusivity terms, all aligned for direct comparison.
In Progress TBD
LOI negotiation guide · key terms, walk-away thresholds
Mike's playbook for which terms to push, which to accept, and where the actual walk-away points are by deal type.
In Progress TBD
Exclusivity agreement · 60–90 day window with extension
The artifact that locks the deal into diligence with one buyer. Negotiated to give Next Mile leverage if the buyer drags or chips.
In Progress TBD
Walk-away threshold · establish floor before negotiation
Mike and the seller agree on the walk-away number before negotiation starts. Prevents emotional decisions when a buyer pushes hard.
In Progress Mike leads negotiation · Wally on seller emotional management
LOI translation call · "here's what this means in plain English"
LOIs are written in legal and financial language sellers have not seen before. This call decodes earnout mechanics, escrow holdbacks, reps and warranties.
In Progress Mike leads negotiation · Wally on seller emotional management
Best Value framework · price vs structure vs cultural fit
How Mike helps the seller see that the highest gross number isn't always the best deal. Cash mix, earnout risk, fit all factored.
In Progress Mike leads negotiation · Wally on seller emotional management
Counter-offer script · push back professionally
How to push back on terms without breaking the relationship. Negotiation moves that protect leverage and signal seriousness.
In Progress Mike leads negotiation · Wally on seller emotional management
Go/No-Go alignment · ready to sign + understand exclusivity
Final check before signing exclusivity. The seller understands what they're giving up (other buyers) and what they're getting (a 60 to 90 day path to close).
In Progress Mike leads negotiation · Wally on seller emotional management
1 Have
9 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = LOI., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: LOI signed · exclusivity executed. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: advance to 09 Diligence
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 08
CompanyContactNoteRep
TBD
Dashboard · Live in HubSpot
LOIs received
Days to LOI signed
Walk-away rate
Exclusivity period to close ratio
Plays that feed this stage

This stage is internal to the deal lifecycle — no acquisition plays feed it directly. Work in this stage is execution against deals already advanced from prior stages.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 08's Stage Play actually addresses what the prospect is experiencing.

  • "LOIs explained in plain English": Legal language is the buyer's home turf. → Served by step 06 (LOI translation call) and step 07 (Best Value framework). The translation call is non-negotiable; the seller cannot make a $50M decision while still googling "what is an earnout."
  • "Side-by-side that compares what actually matters": Headline number is the wrong anchor. → Served by step 02 (LOI comparison matrix) and step 07 (Best Value framework). The matrix shows cash mix, earnout terms, escrow, reps and warranties, structure — not just price.
  • "Permission to walk away if neither is right": Walk-away discipline is the seller's leverage. → Served by step 05 (Walk-away threshold) established before LOIs land. The discipline: agree on the floor with Mike before negotiation starts. After numbers land, emotion takes over.
Use this when

Preparing for the first LOI translation call with a seller. Coaching a deal team on Best Value framing. Reviewing whether walk-away thresholds were set with the seller before bids arrived (the most common mistake).

Stage 09 · Sellers Play

Diligence & Close.

The longest stretch
Manage the 60-90 day diligence and PA negotiation. Defend the valuation against re-trade attempts. Get to wire.
Owner · Mike runs diligence coordination · Wally manages seller fatigue
Exit · Wire transferred · PA executed → advance to 10 Transition
CRM Stage · Mike's CRM → HubSpot Sales Pro · Diligence
Jump to
01 · The Flow

How a deal moves through Diligence & Close..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Manage the 60-90 day diligence and PA negotiation. Defend the valuation against re-trade attempts. Get to wire.
Exit trigger
Wire transferred · PA executed
Advance
advance to 10 Transition
Step
Trigger
Advance
02 · Mindset

Where they're at.

"We're so close. But this process is exhausting. I'm getting questioned about everything and I'm worried the buyer is going to try to chip the price. I just want to get to closing."
What they're doing

Answering 200+ diligence requests. Reviewing the PA with their attorney. Hitting the wall around week six. Wondering if it's worth it. Trying to keep the business running while running the deal.

Who they're talking to

Three legal teams. A CFO. An accountant. Mike daily. Spouse nightly. Still not employees.

What they need to see / feel

Someone defending the valuation when buyers try to chip. Permission to be tired. Reassurance that this is normal, not a sign the deal is falling apart. A clear closing path with a date on it.

What kills the move

Re-trade attempts that go unchallenged. Mike or Wally going quiet. The closing date slipping without explanation. A buyer that nickel-and-dimes after handshake.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
VDR folder structure · standard naming conventions
The virtual data room layout. Standardized so the buyer's team knows where to find what without asking, and so the seller's team can populate quickly.
In Progress TBD
Diligence request tracker · pending/fulfilled/waived per buyer
Every diligence request logged with status. Prevents duplicate asks and gives both sides visibility into what's outstanding.
In Progress TBD
Customer/driver release protocol · approval criteria
When sensitive identifiers get released to the buyer. Tied to specific milestones in diligence to protect the deal if things fall through.
In Progress TBD
Re-trade response playbook · common price reduction attempts
Buyers will try to chip price during diligence. This documents the common moves and the responses that defend valuation.
In Progress TBD
Closing checklist · everything before wire transfer
The final review before the wire. All conditions met, all documents signed, all approvals in writing. Nothing left to chance on closing day.
In Progress TBD
Diligence response coordination · seller/buyer/attorneys
Mike is the air traffic controller between three legal teams, a CFO, and a seller. This is the day-to-day operating protocol.
In Progress Mike runs diligence coordination · Wally manages seller fatigue
Deal fatigue management · "we're almost there"
Sellers hit the wall around week 6 of diligence. The script for keeping them in the game without minimizing how hard it is.
In Progress Mike runs diligence coordination · Wally manages seller fatigue
Re-trade response briefing · prep seller for buyer's chip attempt
The pre-meeting briefing when Mike anticipates the buyer will try to reduce price. Frames the seller's response before emotion takes over.
In Progress Mike runs diligence coordination · Wally manages seller fatigue
Purchase Agreement review checklist
Final review of the PA. Mike walks the seller through the document section by section so there are no surprises at signing.
In Progress Mike runs diligence coordination · Wally manages seller fatigue
Closing day prep · what to expect, bring, feel
The closing-day morning briefing. Who'll be in the room, what gets signed when, what the wire confirmation looks like, how to feel about it.
In Progress Mike runs diligence coordination · Wally manages seller fatigue
0 Have
10 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Diligence & Close., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: Wire transferred · PA executed. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: advance to 10 Transition
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 09
CompanyContactNoteRep
TBD
Dashboard · Live in HubSpot
Days to PA executed
Re-trade attempts surfaced
Re-trade attempts defended
Closing date variance
Plays that feed this stage

This stage is internal to the deal lifecycle — no acquisition plays feed it directly. Work in this stage is execution against deals already advanced from prior stages.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 09's Stage Play actually addresses what the prospect is experiencing.

  • "Defending the valuation when buyers try to chip": Re-trade attempts are predictable. → Served by step 04 (Re-trade response playbook) and step 08 (Re-trade response briefing). The discipline: prep the seller before the re-trade conversation, not during. Buyers expect a number to wobble; Mike makes sure it doesn't.
  • "Permission to be tired": Week 6 is the wall. → Served by step 07 (Deal fatigue management · "we're almost there"). Doug's comment: "70% of failed deals are due to seller fatigue." Mike's job: name the wall when it hits, not pretend it isn't there.
  • "Closing date with a date on it": Slippage without explanation kills morale. → Served by step 05 (Closing checklist) tracking every gate, and the discipline of communicating slippage immediately. The discipline: when the date moves, the seller hears it the same day, with the why.
Use this when

Coaching a seller through week 6 fatigue. Briefing the team before a re-trade conversation. Reviewing the diligence request tracker against the actual closing timeline (the gap is where deals slip).

Added June 10, 2026 · Live capture from Mike's UTS / Fitzmark walk-through

Operating Principles.

Four principles surfaced during Mike's deep walk-through of the UTS / Fitzmark diligence on June 10. These are not assets — they are the operating discipline Mike runs Stage 09 against. New team members onboarding to data room work (Ron and Jay both started here on this deal) need these as much as the asset list. Each block tagged with where it surfaced; refine as more deals run through this stage.

Added Jun 10
UTS / Fitzmark

VDR folder structure · mirror the checklist.

The buyer-provided data room is rarely set up the way you need it. Mike's pattern on UTS — even though Fitzmark forced SharePoint as the platform — was to go in and rebuild the folder structure to mirror Next Mile's standard. Three top-level categories: Financial · Tax · Legal. Inside each, a folder for every line item on the buyer's checklist (separate sub-folder for each request rather than 50 files dumped into one folder). Subfolders allow Ron and Jay to track each item independently and let everyone see progress at a glance. Largely a one-time setup that produces leverage across the rest of diligence.

Owner since June 10: Ron + Jay (Mike supervising during education phase). Buyer-facing implication: the data room becomes self-navigating for the buyer's team — reduces “where's X?” pings and signals operational rigor.

Added Jun 10
UTS / Fitzmark

One point of contact · on each side.

Every form of communication moves through one designated point of contact on each side of the deal. On UTS / Fitzmark, Mike established this with the buyer in the first call. Why it matters: sellers and buyers both have outside legal firms, outside accounting firms, and internal teams that all start asking questions in parallel. Without a single channel, repetitive questions multiply — “two weeks ago I know somebody asked this question” — and the seller gets fatigued by the same diligence ask coming through three different channels.

The discipline corollary: every request that comes in for something not on an existing checklist must be added to a checklist. If a question lives in a stray email instead of on the checklist, it gets lost. The checklist is the source of truth.

Operationally: the one-point-of-contact protocol is set in the kickoff conversation with the buyer. The checklist-discipline corollary is the daily work of the diligence coordinator (Mike, transitioning to Ron / Jay).

Added Jun 10
UTS / Fitzmark

Gatekeeper, not attorney.

The boundary Mike emphasized repeatedly during the walk-through. Next Mile reviews data room postings and the purchase agreement from an operational and commercial perspective only. We flag missing items against the checklist. We surface commercial concerns in the PA. We do not make legal recommendations on documents the seller is posting, and we do not advise the seller on legal interpretations of the PA.

Why this matters: if down the road a legal dispute opens between buyer and seller, the buyer's legal team can look for every pocket. We do not want them able to argue that Next Mile was involved on a legal basis — pulling the firm into a dispute that should sit between the seller's counsel and the buyer's counsel.

The specific failure mode to guard against: Jay enjoys legal detail and likes reviewing contracts. Mike has made this point to Jay directly multiple times. The discipline is not about ability — it is about role boundary. The seller has counsel for legal interpretation; Next Mile is the operational gatekeeper.

Added Jun 10
Mike + Wally

Disclaimer practice · on every sensitive post.

Two layers. First: the Next Mile engagement agreement carries data disclaimers — specifically that the firm's analytics and financial models are built on data the seller provides. Garbage-in / garbage-out is named explicitly. If the seller provides inaccurate financials, Next Mile is not liable for reproducing that information downstream. Second: Mike's standing practice is to paste a Dropbox-format legal statement into the comments section of every sensitive data room post. The statement disclaims responsibility for content the seller has authored.

Wally's June 10 ask: consider adding additional disclaimers at the bottom of the most sensitive documents as they move through the later stages — an extra safety net reminding all parties that Next Mile is not acting as legal counsel. Worth surveying the document inventory and deciding which artifacts warrant the additional disclaimer language.

Action item from June 10: Mike to identify sensitive-stage documents that should carry the additional disclaimer band. See To-Dos.

Stage 10 · Sellers Play

Transition.

Announcement & handoff
Smooth handoff to the buyer. Protect the legacy. Set up the alumni relationship that becomes Stage 11.
Owner · Wally leads integration coordination · Mike on post-close coaching
Exit · 90-day post-close review complete · letter signed → advance to 11 Referral Engine
CRM Stage · Mike's CRM → HubSpot Sales Pro · Transition
Jump to
01 · The Flow

How a deal moves through Transition..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Smooth handoff to the buyer. Protect the legacy. Set up the alumni relationship that becomes Stage 11.
Exit trigger
90-day post-close review complete · letter signed
Advance
advance to 11 Referral Engine
Step
Trigger
Advance
02 · Mindset

Where they're at.

"The deal is done. I should feel relieved, but I'm worried about my employees and customers. I want to make sure this transition goes smoothly — my legacy depends on it."
What they're doing

Telling employees on Announcement Day. Calling top customers personally. Writing letters they never thought they'd write. Going home and feeling something they don't have a word for.

Who they're talking to

Finally, employees. Top customers. Vendors. Their wife or husband, in a way that's now different.

What they need to see / feel

That the buyer is treating their people right. That the transition is being managed competently. That Mike or Wally hasn't disappeared the day after close. That the legacy is intact.

What kills the move

A buyer that breaks early integration commitments. Layoffs they didn't see coming. Mike going silent post-close. Anything that makes them regret who they chose.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
50-item integration checklist · ops, finance, HR, customers
The handoff framework. Fifty items across five categories so nothing gets dropped between the seller's institutional knowledge and the buyer's new ownership.
In Progress TBD
Announcement Day comms · scripts for employees, customers, vendors
The most emotionally charged moment of the entire process. Each audience gets a tailored message; timing coordinated to the hour.
In Progress TBD
Tribal knowledge transfer · SOP framework
The structured way to extract what's in the seller's head into documents the buyer's team can actually use. Without it, value walks out the door with the seller.
In Progress TBD
90-day post-close check-in protocol
Three structured check-ins in the 90 days after close. Catches retention problems, integration friction, and emerging earnout issues before they become deal-killers.
In Progress TBD
Seller recommendation letter · request format + draft
The testimonial framework. Pre-drafted so the seller has a starting point and Next Mile has a consistent format for case studies.
In Progress TBD
Closing dinner coordination · celebrate, set up referrals
The night of close. Genuine celebration, but also the first natural moment to ask who else in the seller's network should know about Next Mile.
In Progress Wally leads integration coordination · Mike on post-close coaching
Integration kickoff agenda · buyer + seller team
First combined meeting between the buyer's operations team and the seller's senior team. Sets the tone for how the integration will run.
In Progress Wally leads integration coordination · Mike on post-close coaching
"What's next for you?" post-exit coaching
Sellers spend years preparing for the deal and zero minutes preparing for life after it. Mike asks the harder question so the seller has someone to think out loud with.
In Progress Wally leads integration coordination · Mike on post-close coaching
90-day customer retention review · flag at-risk relationships
90 days after close, a structured review of which customers are at risk. Earnout-relevant for the seller; relationship-relevant for everyone.
In Progress Wally leads integration coordination · Mike on post-close coaching
Recommendation letter request script · timing & framing
When and how to ask for the testimonial. Timing matters: ask too early, the deal still feels in-flight; ask too late, the emotional peak has passed.
In Progress Wally leads integration coordination · Mike on post-close coaching
0 Have
10 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Transition., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: 90-day post-close review complete · letter signed. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: advance to 11 Referral Engine
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 10
CompanyContactNoteRep
TBD
Dashboard · Live in HubSpot
Announcement Day completion
Employee retention 30/60/90
Top-customer retention 90 days
Earnout milestones tracking
Plays that feed this stage

This stage is internal to the deal lifecycle — no acquisition plays feed it directly. Work in this stage is execution against deals already advanced from prior stages.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 10's Stage Play actually addresses what the prospect is experiencing.

  • "The buyer is treating their people right": The seller's biggest fear post-close. → Served by step 04 (90-day check-in protocol) and step 09 (Customer retention review). The discipline: structured check-ins catch problems while they're still fixable.
  • "Mike or Wally hasn't disappeared the day after close": The most common post-close failure. → Served by step 06 (Closing dinner) and step 04 (90-day protocol). The closing dinner is the bridge, not the ending. The structured 30/60/90 calls keep the relationship alive.
  • "The legacy is intact": What the seller measures success by. → Served by step 02 (Announcement Day comms) where the seller's voice gets to land first, and step 08 ("What's next for you?" coaching). The discipline: the seller writes the employee letter, not Mike. Their words. Their legacy.
Use this when

Planning Announcement Day for a deal closing. Designing the 90-day check-in for a recent close. Coaching the seller on the "what's next for me" question that they often haven't asked themselves.

Stage 11 · Sellers Play

Referral Engine.

The alumni voice
Keep alumni close. Convert relationship into referrals. Use their voice (case studies, testimonials) to win new sellers.
Owner · Wally owns alumni relationship cadence · Mike on industry-specific re-engagement
Exit · Referral introduction → new seller → enters 02 Engagement · or case study published
CRM Stage · ★ NEW · HubSpot Sales Hub · Alumni
Jump to
01 · The Flow

How a deal moves through Referral Engine..

From entry to exit trigger. The visual to keep in mind before working any deal in this stage.

Enters this stage
From prior stage advance · or fresh record
Stage work
Keep alumni close. Convert relationship into referrals. Use their voice (case studies, testimonials) to win new sellers.
Exit trigger
Referral introduction → new seller
Advance
enters 02 Engagement · or case study published
Step
Trigger
Advance
02 · Mindset

Where they're at.

"I've been through it. I know what it's like. If I know someone thinking about selling, I'd want them to work with Mike. I just need someone to ask me."
What they're doing

Living a different life. Some retired, some advising, some in their second act. Watching the industry from the outside now. Occasionally hearing from a peer who's where they were five years ago.

Who they're talking to

Peers. Former employees. Industry friends. The network they spent decades building.

What they need to see / feel

That Mike or Wally still remembers them. That Next Mile is doing well by the next sellers. That their story (case study, recommendation, LinkedIn post) is being used in a way they'd be proud of.

What kills the move

Going months or years without contact. A generic newsletter that doesn't sound like Mike. Being asked for a referral without a real relationship check-in first.

03 · Asset Inventory

What we have, what we need.

Asset Status Owner
Alumni check-in sequence · Q1/Q2/Q3/Q4 personal touchpoints
Four personal touches per year per alumnus. Birthday, anniversary of close, holidays, post-close milestone. Keeps the relationship alive without asking for anything.
In Progress TBD
Quarterly newsletter · market insights + deal activity
The mass-market touch that keeps Next Mile in the alumni inbox. Real value, not promotional, so it gets read.
In Progress TBD
Case study template · Story on Purpose has 6 drafts in project
Standardized case study format covering trigger, journey, outcome. Six alumni drafts already in progress through Story on Purpose.
In Progress TBD
Referral request script · 30–90 days post-close
The structured ask, timed to land when the seller is fresh off the win and most likely to know who else is thinking about it.
In Progress TBD
COI introduction script · "I just closed a deal — here's what it looked like"
How Mike opens with a COI right after a close. Specific deal, specific outcome, builds credibility before asking for the next intro.
In Progress TBD
"How's the transition going?" 30-day check-in · genuine
30 days after close, a real check-in. Not transactional, not pre-referral-ask. Just honest interest in how the post-deal life is going.
In Progress Wally owns alumni relationship cadence · Mike on industry-specific re-engagement
Case study request & approval · ask, draft together, sign-off
How the case study actually gets produced. The seller's voice, Story on Purpose's structure, mutual sign-off before publication.
In Progress Wally owns alumni relationship cadence · Mike on industry-specific re-engagement
LinkedIn testimonial / post request
The social-proof ask. A short LinkedIn post or recommendation from the alumnus that lives publicly and gets seen by next prospects.
In Progress Wally owns alumni relationship cadence · Mike on industry-specific re-engagement
Referral ask · "Anyone in your network I should know?"
The actual ask, in plain language. Open enough to surface unexpected names, specific enough that the alumnus can think through their network.
In Progress Wally owns alumni relationship cadence · Mike on industry-specific re-engagement
COI "closed deal" intro script · social proof opener
When alumni naturally come up in COI conversations, this is the opener that turns them into proof points rather than just stories.
In Progress Wally owns alumni relationship cadence · Mike on industry-specific re-engagement
0 Have
10 In Progress
0 Need
Readiness · Partial
04 · Seller's Checklist

What Wally / Mike does.

Before · prep
Walk in ready.
  • Open the deal record in HubSpot. Confirm stage = Referral Engine., owner = you, lead source captured.
  • Re-read the Mindset (left column). Reset your read on what the prospect is experiencing right now.
  • Review the relevant assets in the middle column — confirm you have what you need before the touch.
  • Field validation pending: stage-specific prep steps will populate from call analysis. Current items reflect the universal pre-call discipline.
During · the touch
Match the mindset.
  • Open with what they're experiencing — see the Mindset column. Lead with their reality, not your process.
  • Listen for the exit trigger: Referral introduction → new seller. That's what tells you whether to advance.
  • Avoid the failure modes in the Mindset's "What kills the move" cell.
Field validation pending Stage-specific question sequence and language will populate from the call analysis loop. Voice of Prospect band below will fill with quotes that become the seed for this checklist.
After · within 60 min
Log it, route it, advance it.
  • Log the call note in HubSpot — what they said, what you heard underneath, where this fits in the journey.
  • Update deal stage based on the exit trigger: enters 02 Engagement · or case study published
  • Send the follow-up using the matching HubSpot template — see Asset Inventory for which one.
  • Set the next task with a specific date and a specific reason.
  • Flag for call review if anything surprised you — new objection, new motivation, language that landed unusually well.
05 · Voice of Prospect
Recorded calls in this stage · seller language that should populate the During-call checklist
Awaiting calls
[Pending. No recorded calls yet for this stage. Wally / Mike: send recordings with the header per the call-analysis protocol and quotes land here in the next issue.]
Who's Here · Live CRM · Stage 11
CompanyContactNoteRep
AMAC Doug Hazen (Founder) Closed Sep 2023 Mike
Sutton Transport Ross Bodenheimer (CFO) Closed Q4 2024 · $130M Mike
Freight Solutions Wally Brauer (Founder) Earnout completed Feb 2025 Mike
FreightLink / Sutton Roger & Deanie Harrison 13 months retired Mike
American Group Dan Krivickas (Founder) Inc 5000 · LTL Mike
Carrier Services Carol Bennett (Founder) 2-yr earnout completed Mike
Dashboard · Live in HubSpot
Alumni response rate
Referrals received
Case studies published
LinkedIn social proof velocity
Plays that feed this stage

Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.

Pressure Test · Does the right execution serve the prospect's mindset?

Three checks for whether Stage 11's Stage Play actually addresses what the prospect is experiencing.

  • "Mike or Wally still remembers them": The personal touch is the engine. → Served by step 01 (Quarterly check-in sequence) and step 06 (30-day genuine check-in). The discipline: Mike or Wally personally sends Q1/Q2/Q3/Q4 notes; no marketing automation pretending to be them.
  • "Their story used in a way they'd be proud of": Case studies must serve the alumnus, not just Next Mile. → Served by step 03 (Case study template) and step 07 (Case study request & approval). The discipline: alumnus sign-off before publication, every time. Story on Purpose's 6 drafts are in progress now.
  • "Asked without a real relationship check-in first": The transactional ask kills the relationship. → Served by step 06 (30-day check-in) preceding step 09 (Referral ask). The discipline: never ask for a referral without three real relationship touches first. The check-in is the relationship; the ask is what the relationship makes possible.
Use this when

Designing the Q3 alumni check-in cycle. Drafting a case study request to a specific alumnus. Coaching a future hire on the difference between an alumni relationship and an alumni transaction.

Sellers · Primary game · Active

Sellers.

Founder-led T&L · $20M–$250M revenue · the engine
4
Audience tiers
Cold · Early · Ready · Not Yet
12
Closed deals/yr
3-yr target
TBD
Active deals
in pipeline
The Single Most Important Message

"A guided exit, not a generic broker."

The seller play is the engine. Everything else exists to feed it or serve it. Four audience tiers, each with its own cadence. Cold Targeted are unknown to us; Engaged Early have replied but their timing is unclear; Engaged Ready are active opportunities; Engaged Not Ready are real fits whose timing is wrong. Tier mechanics drive cadence. Cadence drives content. Content closes deals.

Validated with Doug Hazen / AMAC Sutton Transport Freight Solutions FreightLink American Group Carrier Services
Active play · running now

Cold Outbound · Cold Targeted Sellers

The named motion that fills Stage 01 Prospecting with qualified Cold Targeted leads. 4-week multi-touch cadence (email + LinkedIn + phone) against named-account lists. Owner: Wally on outreach, Marketing on cadence ops. Below is the story behind this play — who we're targeting, what we heard them say, where they are in their journey, what triggers them, what we say, where they hang out, who influences them. Then the play in full, the campaigns in flight, and how we measure.

Section 1
Who they are

Founder-led T&L · $20M to $250M.

The audience for the Sellers play. Not one population — four tiers, defined below, each with its own cadence.

Why This Play Is Primary

The engine, and what it runs on.

Sellers is where revenue lives. Every deal, every fee, every reference for the next deal originates here. The other three plays exist to feed this one (COIs), produce its raw material (Buyers, comparables), or catch its long tail (Portal). The seller play earns more attention than the rest combined.

The seller's situation.

Founder-owned T&L businesses in the $20M–$250M range, asset-heavy carriers, asset-lite brokers, or warehousing operators. Owners are 55+, often nearing retirement or burned out. They've built something real. They don't know what it's worth, who the right buyer is, or how to navigate the process without losing the deal or the legacy.

By the time they raise their hand, they've usually been pitched ten times by advisors who didn't know their business. The opening with Next Mile is operator credibility plus a deliberately patient sequence.

The four-tier approach.

The audience is not one population. It's four tiers, each with a different signal strength and a different cadence. The canonical glossary is below — every reference to a tier name in the rest of the play points back to those four definitions.

The TIA campaign segments (Current Pipeline, TIA Attendees, Past Clients, Past TIA Shows, Engaged, LinkedIn, Friends & Family) all map into the four tiers depending on engagement state coming out of TIA. HubSpot lifecycle and lead status fields carry the segmentation forward.

Emerging from calibration · draft

Two persona dimensions the calls revealed.

Phase 1 calibration (3 seller calls) surfaced a second axis the existing tier framework does not yet capture: acquisition experience. Treating an experienced operator-acquirer like a first-time seller costs credibility in the first 10 minutes. Treating a first-time seller like an experienced acquirer costs the pedagogical framing they need. These two stamps are the working hypothesis — not yet adopted. See O&O #20 for the Discuss item.

DRAFT
Persona · A
The Experienced Acquirer.
  • Has bought or sold before. Bruce/UTS: 3 transactions + 1 acqhire as buyer. Travis/Xtreme: 6 acquisitions as buyer.
  • Knows the vocabulary. Earn-outs, employee retention risk, cash at close, deal structure, escrow.
  • Has been pitched before. Won't be impressed by surface credentials. Wants signal, not pitch.
  • Fast-track Stage 04. Skips pedagogical framing. Goes deeper, faster. Operator-to-operator throughout.
Cross-ref: O&O #20 · Seller Archetype Framework · Add the Experienced Acquirer Dimension
DRAFT
Persona · B
The First-Time Seller.
  • Never done this before. Chad/Freight Logistics: zero prior M&A. "We don't sell businesses every day."
  • Needs vocabulary built. Multiples, EBITDA adjustments, owner draws as add-backs, customer concentration discounts.
  • Has scarring or absence. Either no reference for what good looks like, or has heard horror stories from peers.
  • Slower Stage 03 / Stage 04. Pedagogical framing matters. Wally's exit story functions as peer-credibility unlock.
Cross-ref: O&O #20 · Seller Archetype Framework · sequencing of educational content
How this overlays the four-tier framework. The four tiers (Cold Targeted, Cold Engaged, Engaged Ready, Engaged Wrong-Timing) describe engagement state. These two personas describe acquisition experience. A Cold Targeted seller could be either persona; an Engaged Ready seller could be either. Treat them as a second dimension that informs pacing and content depth, not as a replacement for the tier framework. Leadership decision pending — tracked as O&O #20 (Discuss).
Goals by Tier

What each tier is for.

The goal at each tier is different, so the cadence has to be different. Mixing them is the most common reason a generic email blast destroys a high-trust pipeline.

Tier Glossary · canonical definitions

The four seller tiers, in one place.

Every other section uses these names without redefining them. When in doubt, scroll back here.

Tier Goal Success Signal
Cold Targeted Earn the first reply. Qualify into Engaged Early or out. Reply, call booked, content engagement
Engaged Early Deepen relationship. Qualify timing. Move to Engaged Ready. Numbers conversation, value range discussion
Engaged Ready Sign engagement. Run the process. Signed engagement letter
Engaged Not Ready Stay top of mind. Route to portal. Capture when timing flips. Re-engagement when life event hits
The Next Mile Difference

Why we win in T&L.

Not a generalist M&A shop with a transportation page. A sell-side-only, operator-experienced team purpose-built for founder-led T&L exits. These are the wedges that show up in every conversation.

01
Sell-Side Only
We always represent the owner. No buy-side mandates pulling the other direction. Roger and Deanie's framing: "having somebody on your team really allowed us to sleep at night."
02
Operator-Experienced
90+ years combined T&L and M&A. Wally's framing: "somebody that wasn't going to just try to sell me something, but somebody that actually had lived it and breathed it."
03
Compressed Diligence
Proprietary system shortens 6–7 month diligence to 2–3. Dan Krivickas's experience: faster certainty of close, less drag on operations.
04
300+ Buyer Database
Strategic and financial T&L buyers matched to seller goals: financial outcome, people fit, strategic alignment. Health-audit needed (open item).
05
Free Look
No exclusive agreement to start. Free, confidential evaluation. Wally: "The ability that I could get a free look and go through the process was significant for me."
06
Success-Fee Aligned
No upfront retainer, no LOI-stage fees. Success at close. Doug's framing on value: "I wrote Black Belt a letter at the end. I said, you saved me more than your fee."
Pipeline · Strategic View

What's in flight for this play.

Snapshot as of June 10, 2026. This is the strategic / play-oriented view: deals grouped by stage, with the play context for each. The bi-weekly working snapshot lives in The Revenue Meeting · Pipeline — same nine deals, different cut. Reference Alumni (the six VOC interviews that anchor every play in this tab) have moved to Section 2 · Voice of the Customer.

9
Active Deals in Pipeline
5
Stages Active (03 · 04 · 07 · 08 · 09)
$26M+
Named (UTS) · 8 others in formation
1
In Diligence · closing target before fall busy season
Stage 09 Diligence 1 deal · defending valuation · closing path
Bruce Parsons · UTS / Fitzmark
Source · long-tracked relationship

Where the play is working: Mike's diligence coordination posture (gatekeeper, not attorney — see Stage 09 · Operating Principles). One-point-of-contact protocol established with the buyer. Data room mirrored to checklist structure. Ron and Jay onboarded to data room management.

Watch: Owens Corning concentration risk (see O&O #38). Bruce’s largest account is Owens Corning; Fitzmark also services Owens Corning at a different region/plant. Worth documenting proactively rather than reactively in diligence.

Stage 08 LOI 3 deals · mixed momentum · advancing, stuck, on-hold
WTS · Western Canada
Source · outbound · small Canadian profile

Play motion: LOI redline cycle. Mike walked the redlines verbally with buyer’s rep before forwarding. Buyer has investor meeting Thursday, committed to Friday response. 45–60 day diligence estimate.

Watch: small + Canadian profile makes this structurally tough; advancing is the win regardless of size.

Freight Logistics · (Wally referral)
Source · Wally referral (early COI engine signal)

Play motion: competitive LOI — pushing 3 buyers (ITF, Dynamic Connections, one more) to surface competing valuations. Mike's coaching email yesterday on ITF’s under-market offer.

Watch: seller losing patience — doesn’t want to blow up ITF LOI but knows the offer is light. Goal: get competing numbers fast.

Challenger Freight · Dallas / DFW
Source · on hold

Play status: on hold. Buyer altered terms to ask for $1M cash-at-close as a loan; one of three owners pulled after consulting an outsider.

Watch: realistic restart closer to end of year — once a 100% cash-at-close buyer surfaces.

Stage 07 Connected 2 deals · new buyer introductions in flight
FastExact · Bay Area, CA
Source · outbound · concert & trade show freight specialty

Play motion: active buyer-matching. Alan Lund passed yesterday; Mike opened Landstar (~$5B agent organization) same day. Strong fit because Landstar can route small-deal profiles to specific internal agents.

Watch: sub-$5M and California — small profile makes the buyer pool thin. Landstar relationship could become a recurring pipeline for similar deals.

Map Parcel Express · San Diego
Source · long-tracked · family-owned

Play motion: watching. Owner originally presented at ~5x multiple ($20M EV); came back asking 6.5x. Friendly competitor returned a poor offer.

Watch: seller expectation gap — market won’t deliver 6.5x at this size. Holding until seller realigns or new buyer signal emerges.

Stage 04 Evaluation 1 deal · valuation forming · expectations gap forming
Extreme Trucking
Source · long-tracked · asset-based

Play motion: revised valuation work. Updated financials in this week. CFO normalization conversation yesterday. Initial valuation relied on $500K normalized-expense assumption; few actual normalized expenses materializing — revised number likely lower than first read.

Watch: open question whether seller still wants to go to market once the revised number lands. The seller mindset shift here will tell us a lot about the play’s diagnostic-posture working.

Stage 03 Education / Portal 2 deals · long-term plays · Customer Portal subscribers
Paystar
Source · long-tracked · contract-based $30M brokerage, 7 customers

Play motion: patient re-engagement. Previous buyer pool passed on customer concentration. New buyer interested specifically in contract-based deals; Mike reaching out repeatedly. Awaiting reply.

Watch: customer concentration (7 customers) is the structural issue that will define any valuation outcome.

Travis Nelson · Jetliner Alkaos
Source · TIA event · Customer Portal subscriber

Play motion: Portal track (the “not yet, not no” path). Initial acquisition conversation surfaced “not ready”; signed engagement for Customer Portal subscription. Recent shift: asking about acquisition fees — possibly leaning toward going to market.

Watch: no money received yet on the portal subscription. Anchors the open question in O&O #44 — what stage are Customer Portal subscribers actually in?

What this view says about the play. Nine deals across five stages. One in Diligence (UTS) is the strong-quality close that bodes well for the cadence going forward. The Stage 08 LOI band (WTS, Freight Logistics, Challenger) shows mixed momentum — advancing, competitive pressure, and a hold. Two Stage 03 long-plays (Paystar, Jetliner) are the patient re-engagement track. The Reference Alumni (Doug, Ross, Wally, Harrisons, Dan K, Carol) anchor the voice underneath every script and message in this tab — they sit in Section 2 · Voice of the Customer.
What's Inside

The Sellers play in operational order.

From strategy through to running campaigns. Each sub-tab is one step in how a salesperson would actually use this play.

01
OverviewStrategy, goal, market, the Next Mile difference, pipeline snapshot
✓ Complete
02
Triggers & AudienceThe Owner's Journey, lifecycle, 10 trigger moments, CEPA, four tiers, TIA mapping
✓ Complete
03
Messages & NarrativeCore narrative arc, named scripts referenced from the Pipeline
✓ Complete
04
ConversationDiagnostic conversation arc, interview guide, Go/No-Go, objection-handling matrix
✓ Complete
05
Network & COIsWhere sellers gather, who whispers (cross-link to COIs)
Awaiting · editorial roadmap
06
Campaigns & AssetsTier transitions, sequencing, CTAs by stage, channel mix, LinkedIn, programmatic, Exit Readiness Library, campaign flow
✓ Complete
07
Budget & VOCVoice of the Customer (Budget pending)
Partial · VOC present, Budget pending

We know who they are. Before we describe how we reach them, we need to hear them in their own voice — what they actually said when they made the decision to sell.

Section 2
What we heard them say

Voice of the customer.

Verbatim quotes from alumni and prospects, captured in interviews and recorded calls. These anchor every asset, every script, every play in the document. When something here gets quoted on a slide, it's because a seller said it — not because a marketer wrote it.

Source · the six interviews

Reference alumni.

Six customer journeys. Roughly 40–50 content pieces from these interviews alone. Each one cuts into long-form case study, short-story email, quote pulls, video script, and an educational angle. The voice underneath every Stage script and every brand asset in this tab traces back here.

Reference Alumni · Six Customer Journeys · ~40–50 content pieces from these interviews alone
Doug Hazen · AMAC
Seller fatigue · partner death
4-year journey · "saved more than the fee"
Ross Bodenheimer
Sutton Transport · CFO POV
$130M · 13 terminals · "abnormal asks"
Wally Brauer
Freight Solutions → Partner
Faith & grit · client-to-partner arc
Roger & Deanie Harrison
FreightLink / Sutton
First deal fell through · second closed
Dan Krivickas
American Group
Cultural fit · compressed diligence
Carol Bennett
Carrier Services · 38 yrs
"The business was me" · founder dependency

Source: Six interview transcripts in project. Each one cuts into long-form case study, short-story email, quote pulls, video script, and an educational angle. Roughly 40–50 distinct content pieces from interviews already done.

Voice of the Customer

What alumni actually said.

Verbatim. No paraphrasing. These are the quotes that anchor every asset in the seller play.

"I wrote Black Belt a letter at the end of the process. I said, you saved me more than your fee. That's what I'll call value."

Doug Hazen · Founder, AMAC

"For any business owner that has never done a sale, you really don't know anything about it. You just don't."

Doug Hazen · Founder, AMAC

"It made the transaction easier because we had a partner that was fighting for us. They were invested in our interests, not just our ownership interests, but also what our interests were for our employees post-transition."

Ross Bodenheimer · VP Finance, Sutton Transport

"Next Mile was really good at saying, 'Hey, that's an abnormal ask. That would not be something that is part of a normal transaction.'"

Ross Bodenheimer · VP Finance, Sutton Transport

"Somebody that wasn't going to just try to sell me something, but somebody that actually had lived it and breathed it."

Wally Brauer · Founder, Freight Solutions

"Having somebody on your team really allowed us to sleep at night. He was looking after our best interests."

Roger & Deanie Harrison · Founders, FreightLink

"For us, it was all about being able to trust the person representing us. And Mike and Black Belt have the utmost integrity."

Dan Krivickas · American Group

"The business was me. It was me because I was the one who cultivated all of the customers. I wanted them to really be in good hands when we made this transition."

Carol Bennett · Founder, Carrier Services

John Knicely · Exit Readiness Library: John's content plan is the Exit Readiness Library on nextmilema.com. Five categories, ~28 titles. The six Real Client Stories map directly to these alumni interviews. Educational categories (Exit Readiness & Planning, Understanding the Process, Industry-Specific Insights, Deal Structure & Terms) carry the rest. See companion Campaign Flowcharts document for which library title lands at which touch in each tier.

Those voices tell us what mattered to sellers after the decision. Next: where they are in the longer journey that leads to that decision.

Section 3
Where they are in their journey

The T&L Owner's journey.

Most T&L founders spend 20+ years in the business before they consider an exit. 65% of family businesses don't survive the first generation. 70% of failed deals are due to seller fatigue. This is the lifecycle map — and the mindset triggers that move owners from Stage 4 Maturity into Stage 5 Exit Window. The question isn't where the audience is. It's where they are and what they're thinking when they need us.

Strategic Framework

The strategic framing.

A lifecycle map of the T&L company founder from first load to final close. The question isn't where the audience is. It's where they are and what they're thinking when they need us. Most owners spend 20+ years in the business before they consider an exit. 65% of family businesses don't survive the first generation. 70% of failed deals are due to seller fatigue. This framework is how we recognize the moments that matter and time our outreach accordingly.

The Starbucks analogy.

A mom walks into Starbucks thinking about her morning. She walks out, slows down, hears music, and thinks about her kid. Same location. Different moment. Different mindset.

T&L owners are at industry conferences, in their CPA's office, on a vacation they haven't taken in years. The question is: when are they finally open?

Why this lives under Sellers.

The 7-stage lifecycle is the source of the seller tier framework. Stage 4 Maturity into Stage 5 Exit Window is Next Mile's primary territory. The 10 mindset triggers are the prompts that move a Stage 4 owner into the Exit Window and become Engaged Early or Engaged Ready. The CEPA matrix is how we tier qualified sellers once they're engaged.

This framework also drives the COIs play — every vendor on the journey is a potential COI for the moment they own — feeds the COIs play. See Appendix · TIA Handout for the customer-facing version we distributed at Booth #218.

The Lifecycle

Seven stages of a T&L company.

From first load to final close, and every vendor relationship in between. Each stage has a revenue band, a typical age range, a mindset quote, and the advisors most active at that stage. Stage 5 (Exit Window) is where Next Mile belongs.

01
Launch
$0–$5M · Year 0–3 · Owner age 30s–40s
"Prove it works. Just survive."
Left a carrier. Relationships = revenue. Everything is manual.
Load board · Factoring · Insurance · Basic TMS
02
Traction
$5M–$20M · Year 3–7 · Owner age 35–45
"Build the machine."
First real hires. Systems start forming. This might actually work.
Factoring · TMS · Staffing · CPA · Insurance broker
03
Growth
$20M–$75M · Year 7–15 · Owner age 40–55
"How big can we get?"
Leadership team forms. First acquisitions. "What's this worth someday?"
TMS · Staffing · CPA/Tax · Banking · Coach
04
Maturity
$50M–$200M+ · Year 12–25 · Owner age 50–65
"Is this still fun? What's next for me?"
Owner is 50s–60s. Growth has slowed. Risk/reward shifting.
Wealth manager · CPA · Banking · Business coach · Valuation
06
Active Process
12–24 months · Owner age 58–68 · Engaged
"Don't screw this up. Protect what I built."
CIM, buyer meetings, LOI, due diligence, closing.
M&A advisor · Transaction attorney · CPA/QoE · Banker
07
Post-Close
Earnout + beyond · Owner age 60–70 · 1–2 year transition
"Did I do the right thing? What's next?"
Earnout period. True exit. Becomes a referral source.
Wealth manager · Tax advisor · Next chapter coach

Real triggers from the VOC.

Wally B. Hit $100M goal. Needed capital to bolt on acquisitions. Wanted a strategic partner.
Ross B. Business grew 3x. Risk profile changed. Second-gen ownership decision point.
Roger H. Italy vacation. Slowing down. Mike's email arrived at exactly the right moment.
Doug H. Partner died. COVID hit. 7-year journey. Seller fatigue nearly ended the deal.
Carol B. Bad first advisor. Felt like a transaction. Found the right fit when trust was rebuilt.
The Open Moments

10 triggers that shift a founder's mindset.

"If you want to teach guitar, you don't put a flyer on the Starbucks job board. You sit outside with your case open and play music as they walk out with their coffee. You have to be there when they are relaxed, present, and open." These 10 moments are when the T&L owner's case is open. Our content and outreach are calibrated to find owners in one of these moments.

01
The Rare Vacation
Slowing down enough to finally think about the future instead of the daily grind.
VOC: Roger H. in Italy when Mike's email arrived.
02
The Growth Ceiling
Hitting a major milestone but realizing they need capital or a strategic partner to go further.
VOC: Wally B. hitting his $100M goal.
03
The Partner Dynamic
A partner wants out, or a sudden tragedy forces an immediate change in ownership structure.
VOC: Doug H. dealing with partner death.
04
The Succession Gap
The realization that the next generation (kids or leadership team) doesn't want to take over.
05
The Peer Exit
Watching a competitor or friend sell their business and wondering, "What is mine worth?"
06
The Risk Fatigue
A bad year, a market shift, or a lost major client that makes the daily grind feel unsustainable.
07
The CPA Reality Check
A sobering conversation about tax exposure, wealth concentration, or estate planning.
08
The Banker Conversation
Realizing the personal guarantee required for the next phase of growth is too high a risk.
09
The Industry Event
Walking the floor at TIA, seeing the M&A activity firsthand, and feeling the market shifting.
10
The Perfectly Timed Email
An unsolicited outreach that lands exactly when the owner's mindset has already shifted.
VOC: Roger & Wally both responded to cold outreach.
CEPA Qualification Matrix

Two questions that qualify every referral.

Once an owner is engaged, the CEPA framework tells us how to tier them. Business attractiveness (25 factors across business, forecast, market, investor) on one axis. Personal readiness (11 factors covering plans, financial preparedness, advisory team, family awareness) on the other. Most owners overestimate their business attractiveness and underestimate how unprepared they are personally. Mapping where a seller falls determines how Next Mile engages.

The Motivated Seller
Low Attractiveness · High Readiness
Owner is personally ready to exit but the business needs work. Concentrated customers, owner-dependent operations, or weak financials will suppress the multiple.
Next Mile's role: Value Acceleration planning. Help them close the Value Gap before going to market. 12–24 month runway.
The Ideal Seller ★
High Attractiveness · High Readiness
Business is buyer-ready. Owner has a personal plan, knows what they need, and is emotionally prepared. This deal closes cleanly at a premium multiple.
Next Mile's role: Run the full process. Maximize value. Protect the seller. This is the engagement that generates the best outcomes and the best referrals.
Not Yet
Low Attractiveness · Low Readiness
Too early in the journey. Business and owner both need significant development before a transaction makes sense.
Next Mile's role: Plant the seed. Stay in the ecosystem. Refer to a CEPA or business coach. Come back in 3–5 years.
The Reluctant Seller
High Attractiveness · Low Readiness
Great business, but the owner hasn't defined what life looks like after the sale. No personal plan. No wealth goal. They'll get cold feet at the LOI stage.
Next Mile's role: Help them build the personal plan first. Refer to a CEPA or wealth advisor to define the post-sale vision. Then run the process.

Mapping to seller tiers: The Ideal Seller maps to Engaged Ready. The Reluctant Seller maps to Engaged Not Ready and is the population the Portal is designed to capture. The Motivated Seller becomes Engaged Early nurture with Value Acceleration content from John's library. Not Yet stays in the long tail. Confirm this mapping with Mike + Wally on the next Tuesday meeting.

Four Tiers

Where every seller lands.

Each tier is a different population with a different goal, a different cadence, and a different content mix. HubSpot lifecycle stage drives tier assignment; tier transitions drive workflow.

Tier referenceThe Cold Targeted / Engaged Early / Engaged Ready / Engaged Not Ready definitions live in Section 1 · Tier Glossary. The blocks below add color, sources, and goals on top of those definitions.
Cold
Targeted
Targeted Cold

Sellers who match our profile but have never engaged. Sourced from list-building (ZoomInfo, profile-match queries) or directories like the TIA member list. Asset-based, asset-lite, or non-asset T&L businesses, $20M–$250M revenue, founder-led.

GOAL: Earn the first reply. Qualify into Engaged Early or out.
Early
Conversation started
Engaged Early

Sellers in the pipeline who have had at least one conversation but aren't yet committed. Low or unclear intent, timing uncertain. The "kicking tires" stage.

GOAL: Deepen relationship. Qualify timing. Move to Engaged Ready.
Ready
Ready to engage
Engaged and Ready

Active opportunities. Either ready to sign or close to it. Highest priority for high-touch follow-through. No automation here. This tier gets relationships, not sequences.

GOAL: Sign engagement. Run process.
Not Ready
Not yet · Portal candidate
Engaged But Not Ready

Sellers we know, like, and would represent. The timing is wrong. Wrong age, wrong life stage, business not ready, market timing off. Goal is to keep them in orbit until timing flips. The Portal section below is the soft handoff.

GOAL: Stay top of mind. Route to portal. Capture when timing flips.
TIA Segment Mapping

From the TIA campaign into the tiers.

The TIA campaign segments don't disappear. They get re-tiered based on engagement state coming out of the show. This mapping is the source of truth.

TIA Segment Lands in (Sellers play)
Current PipelineEngaged Early / Engaged Ready
TIA Attendees (replied)Engaged Early
TIA Attendees (no reply)Cold Targeted (still cold)
Past ClientsEngaged Not Ready · alumni as advocates
Past TIA ShowsCold Targeted
Engaged contactsEngaged Early
LinkedIn networkCold Targeted
Friends & FamilyEngaged Early / Engaged Not Ready

The journey gives us the when. The triggers above gave us the why now. With both, we know which signals to watch and what to say when we see them.

Section 4
What we say to them

The narrative arc.

Not a pitch. A diagnosis. The story Next Mile tells when a seller picks up — operator-voice, only-sellers, success-fee only, free look. The arc runs through every cold email, every voicemail, every 15-minute fit call. Anchored in alumni proof, not generic M&A language.

Core Narrative

The story Next Mile tells when a seller picks up.

Not a pitch. A diagnosis. The narrative arc that runs through every cold outreach, every voicemail, every email and every 15-minute fit call. Anchored in alumni proof, not generic M&A language.

Open with operator credibility

Mike spent decades in transportation. Wally built and sold his own brokerage. The opener doesn't lead with M&A vocabulary; it leads with what kept the seller up last night. Driver shortages, insurance verdicts, the partner who wants out, the kid who isn't coming into the business. The line that sets it apart: "we get it because we lived it."

Acknowledge the noise

Every T&L owner with $20M+ in revenue gets called by 5 to 15 M&A firms a week. Most calls die in the first 20 seconds. Mike and Wally don't fight that noise; they name it. "You probably ignore most of these calls. We're trying to be less annoying than most by actually understanding your business before we waste your time."

Lead with proof, not promise

The Exit Readiness Library, the named alumni stories (Doug, Ross, Wally, Roger & Deanie, Dan, Carol), and the proprietary analytics engine all sit behind the conversation. Sellers don't want hype; they want evidence the firm knows their world. Doug Hazen: "He's a straight shooter. He doesn't care if it's what you want to hear or not."

Offer a free look, not a commitment

Next Mile's fee structure (no upfront cost; success-fee only) removes the biggest barrier sellers cite. The narrative invites a no-cost diagnostic. Wally's framing as a former seller: "The ability to get a free look and go through the process without paying anything was significant for me."

Match the cadence to the readiness

Cold Targeted (ready) gets the operator-voice cold opener and Soft Ask. Engaged Early (engaged) gets the 90-day re-engagement script. Engaged Ready (engaged not ready) gets monthly educational email + Portal context. Engaged Not Ready (engaged but ready) gets the break-up email if quiet, but the door stays open. The narrative doesn't change; the channel and intensity do.

Scripts in Flight

Named seller-facing scripts live in the Pipeline.

Each script below exists as a Play step in the Pipeline tab. Click through to see the full why-context and ownership. These are the messaging artifacts a salesperson actually runs.

That's the story. Next: how it plays out in a real conversation.

Section 5
How the conversation goes

Diagnostic, not interrogation.

Sellers come in skeptical. They expect a sales pitch. The Next Mile conversation moves from operator-language credibility ("we get it"), through diagnostic questions that surface real intent, into qualification of whether selling is right and right-now.

How the Seller Conversation Goes

Diagnostic, not interrogation.

Sellers come in skeptical. They expect a sales pitch. The Next Mile conversation moves from operator-language credibility ("we get it"), through diagnostic questions that surface real intent, into qualification of whether selling is right and right-now. The structure is in the Pipeline. The artifacts that drive it are below.

01
15-minute fit call · Stage 02 Engagement

Light touch. Confirms the inbound interest is real. Not a discovery call yet. Routes the prospect into Stage 03 (Education, if not ready) or Stage 04 (Evaluation, if ready). Owner: Wally for sellers; Mike for high-value sellers and buyers.

02
Discovery booking flow · Stage 02

If the fit call lands, the discovery conversation gets booked. Calendar friction is zero (HubSpot Meetings or direct calendar invite from the Soft Ask flow). The discovery is the first real diagnostic.

03
Seller interview guide · "Why are you selling?" · Stage 04 Evaluation

The diagnostic question set. Surfaces the actual driver behind the inquiry (retirement, partner exit, health, market timing, burnout, growth-capital need). Doug Hazen: "He never told me what I wanted to hear. He just told me how it was." That posture starts with this conversation.

04
Go/No-Go conversation · Stage 04 Evaluation

The decision point. Either the seller proceeds to engagement (Engaged Early → Engaged Ready) or stays in education (Engaged Early → Engaged Not Ready). Roger Harrison: "I felt like Mike really represented our interests as well as he could." That representation begins by being honest about whether now is the right time.

We know what we say and how the conversation goes. Now: where do these sellers actually hang out, and who's whispering in their ear when they're thinking about exit?

Section 6
Where they hang out

The rooms they're actually in.

Sellers don't read M&A blogs. They go to TIA, attend regional carrier-group meetings, sit on industry boards, read niche operator newsletters. Channel strategy follows where the audience already is — not where it would be convenient for marketing.

Channels · validated

Where Cold Targeted targets actually gather today.

A working list of channels we know work for Cold Targeted reach. Refined as Mike and Wally report back from the field.

  • TIAThe annual show is the single biggest concentration of Cold Targeted targets. Post-TIA waves have produced the most pipeline this year.
  • Regional carrier groupsState trucking associations and regional 3PL chapters. Mike attends; Wally has speaking opportunities.
  • LinkedInCold Targeted founders use it. Operator-voice DMs land; corporate-broker outreach gets ignored.
  • Peer networks & alumni introductionsThe warmest channel by far. Alumni-introduced Cold Targeted targets convert orders of magnitude higher than cold lists.
  • Industry newsletters & podcastsFreightWaves, Heavy Duty Trucking, niche operator podcasts. Sponsorship and guest appearances tested selectively.

This list is intentionally short. As the call analysis loop runs and we hear sellers reference where they were when they first heard of us, this section gets more specific.

Knowing where they are matters most when we also know who they listen to. The next layer is the COI network — the peers and advisors whose recommendation opens the door faster than any cold outreach.

Section 7
Who influences them

Centers of influence.

When a Cold Targeted target hears Next Mile's name from a peer, an advisor, or a trusted industry voice, the door opens twice as wide. COIs (Centers of Influence) are the relationships that produce those introductions — and they have their own play.

COI Summary · for the Sellers play

Five tiers of influence.

Centers of Influence (COIs) are the relationships that produce warm introductions, signal what's coming, and validate Next Mile when a Cold Targeted target hears the name. They have their own play — the full execution lives in the COIs tab — but the Sellers play needs to know who they are, because every part of the seller story is influenced by them.

Tier 1
First to know an exit

The COIs who see the risk patterns and ownership conversations before the owner says "exit" out loud. They get the call when something is starting to shift.

Examples: Insurance brokers (commercial & key-person), trust & estate attorneys, succession-focused wealth managers, family-office advisors.
Tier 2
Active referrers · operator network

The COIs who already refer T&L founders. They know the M&A landscape, they have opinions, and they decide who they hand off to.

Examples: CPAs and tax advisors serving the T&L vertical, industry attorneys (transactional, regulatory), peer-group operators (alumni, board members of regional carrier associations), exit-readiness coaches.
Tier 3
Industry-adjacent · validators

The COIs whose endorsement adds credibility without typically producing direct referrals. They're the "I asked around and three people said Next Mile is the real one" sources.

Examples: Industry-association staff (TIA, ATA, state carrier groups), trade-press editors and podcasters, conference programmers, vendor-side leaders (TMS providers, factoring companies, capital partners).
Tier 4
Buyer-side intelligence

The COIs on the buyer side of the table whose information flow back to Next Mile sharpens both buyer-matching and seller positioning. Closer to Buyers than to COIs, but listed here because they shape what we say to sellers.

Examples: Strategic-acquirer corp dev contacts, PE firm partners and operating advisors, family-office direct-investment leads.
Tier 5
Adjacent · long-tail relationships

The COIs who aren't currently active referrers but should be on the radar — relationships worth maintaining at low touch for the long game.

Examples: Past alumni who've sold and moved into next ventures, retired operator-investors, broader business-advisor networks (BBTC peers, RIA wealth-manager circles).

We know who they are, what they say, where they are, what triggers them, what we say back, how it plays out in conversation, where they hang out, and who influences them. Time for the action layer — the named plays we run.

Section 8
The plays we run

Named motions that fill the pipeline.

A play is a repeatable named motion with a defined goal. Each one feeds a specific stage of the 11-stage Playbook. Cold Outbound is the only one built in full; the rest are placeholders that follow the same 8-element structure when the prototype validates.

Sellers · Plays Library

Named motions that fill the pipeline.

A play is a repeatable named motion with a defined goal — different from the 11-stage Playbook which describes the journey a deal travels. Each play feeds a specific stage. The first play built in full is Cold Outbound · Cold Targeted Sellers, the engine that fills Stage 01 Prospecting. Other plays will follow the same 8-element format once this prototype is validated.

Feeds Stage 01 · Prospecting
Active · running

Cold Outbound · Cold Targeted Sellers

4-week multi-touch cadence · email + LinkedIn + phone
Pending

COI Referral Activation

Inbound from COI · warm intro motion
Feeds Stage 02 · Engagement
Pending

Post-TIA Reactivation

Post-show re-engagement of conference contacts
Pending

Alumni Referral Loop

Stage 11 → Stage 02 · alumni-introduced sellers
Feeds Stage 03 · Education
Pending

Engaged-Not-Ready Re-Engagement

Reactivate Engaged-Not-Ready sellers · 90-day script
Pending · linked to Portal section

Portal Engagement · Sellers Database

Marketing motion · invite database to Portal's operator view
Feeds Stage 04 · Evaluation
Pending

Engaged-Ready Nurture

Highest-priority active opportunities · no automation, relationships
Active play · feeds Stage 01 Prospecting

Cold Outbound · Cold Targeted Sellers.

The named motion that fills Stage 01 with qualified Cold Targeted leads.
Owner · Wally (Cold Targeted outreach) · Marketing (cadence ops)
Status · Active · In Flight
Cycle · 4-week multi-touch
01Strategy & Triggers

When to run this play.

Summary

Cold Targeted is cold targeted — sellers who match Next Mile's ICP but have never engaged. They're sourced from list-building (ZoomInfo, profile-match queries) or directories like the TIA member list. The play earns the first reply by leading with operator credibility and Next Mile's structural difference (only-sellers, success-fee only, no upfront cost), not with M&A vocabulary.

Triggers · run this play when
New named-account list ships (ZoomInfo, TIA directory, LinkedIn profile-match) Post-event follow-up (TIA show, peer-group attendance) COI surfaces a peer who's "thinking about it" Stage 4 Maturity → Stage 5 Exit Window mindset shift detected (signal: equipment refinance, partner buyout question, retirement timeline mention) Pipeline gap — <30 deals in Stage 01 Prospecting
Use case

The default outbound motion against any newly-tagged Cold Targeted contact. Not used for Engaged Early, Engaged Ready, or Engaged Not Ready — those tiers have their own plays.

02Goals & Success Metrics

Earn the first reply.

The target

Convert a Cold Targeted contact to Engaged Early by earning the first reply and booking a 15-minute fit call. Success is the contact crossing into Stage 02 Engagement — a real conversation, not just an open.

KPIs · success metrics
Reply rate · 4-week sequenceTarget TBD
Conversion Cold Targeted → Engaged EarlyTarget TBD
Fit calls booked / cohortTarget TBD
Cycle time · first touch to first reply≤ 14 days
List exhaustion · % opted-out + % unresponsive after 4 weeksTarget TBD
Field validation pending Numerical targets will be set after analyzing the post-TIA outreach data already in HubSpot. Cycle-time data exists for the TIA waves; reply-rate baselines need to come from those campaign reports before we set thresholds.
03Target Buyer Persona

Cold Targeted Sellers.

The audience

Founder-owners of T&L businesses — asset-based, asset-lite, or non-asset — in the $20M–$250M revenue band. Most are 55+, near retirement or burned out, often the original founder or first-generation acquirer. Decision-maker is almost always the owner; the CFO doesn't get involved until LOI.

Pain points · what they care about
  • Don't know what their business is worth — heard wildly different multiples from advisors and "guys at the bar."
  • Don't know who the right buyer is — strategic vs. financial, what tradeoffs each implies.
  • Have been pitched ten times by advisors who didn't know their business — broker-language, M&A jargon, no operator credibility.
  • Worried about losing the deal — confidentiality leaks, staff finding out, customer reactions.
  • Worried about losing the legacy — wrong buyer dismantles what they built; right buyer continues it.
  • Don't trust upfront-fee advisors — Wally's actual experience: "the ability to get a free look without paying anything was significant for me."
04Buying Stage

Pre-pipeline → Stage 01.

Pipeline alignment

Cold Targeted contacts enter this play before they're in the HubSpot deal pipeline. They sit as Contact Type = Seller, Lead Status = Cold Targeted in HubSpot. The goal of this play is to advance them to Stage 01 Prospecting (form fill, phone call, or direct reply) and then into Stage 02 Engagement (15-min fit call).

In the 7-stage company lifecycle

Most Cold Targeted targets are in Stage 4 Maturity of their company's lifecycle — the business is established and profitable, but the founder is starting to ask questions about what comes next. The play's mindset triggers (equipment refinance, partner buyout, peer who just sold) are the catalysts that move them toward Stage 5 Exit Window.

Exit from this play

The contact replies (any channel), schedules a call, or hits a re-engagement signal threshold. At that point they advance to Stage 02 Engagement and exit this play.

05Discovery Questions

Earn the conversation.

The discovery questions below are designed for the first reply / first conversation — the moment the cold contact starts engaging. They're not interrogation; they're pain-focused, open-ended, and led by curiosity. Save quantitative qualification (revenue, EBITDA, multiples) for the 15-min fit call in Stage 02.

The opener · what's changed
  • "What's changed for you in the last 6 to 12 months that made you open this?"
  • "What were you hoping to find when you replied — or was it more of a 'curious' click?"
Pain — what's driving the question
  • "Is this something you're actively exploring, or just keeping an eye on?"
  • "What would make this worth a real conversation for you?"
  • "Have you talked to anyone else about a potential transition — advisor, peer, family?"
Disqualify — if any of these surface, route differently
  • "Are you under any active letter of intent or exclusivity right now?" (If yes — different play.)
  • "Is there a co-owner or partner whose buy-in this would need?" (If yes — note for fit call.)
Field validation pending The 18 recorded calls Mike has from the post-TIA sequence are the gold for this section. Once analyzed, the actual questions that earned replies — and the language sellers used in those replies — will replace these starting points.
06Messaging & Scripts

Operator-voice, no pitch.

The 4-week multi-touch cadence rotates email, LinkedIn, and phone. The narrative doesn't change channel-to-channel; the format does. The opener leads with industry credibility (Wally's operator background, Mike's Echo/Yellow history), partnership framing, and never a pitch in the first paragraph.

Cold email · operator opener · talking points I spent X years as a [T&L operator role]. We sold the business through Mike and Next Mile a few years back. The thing that mattered most to me was that they only represented sellers — there's no buyer in their pocket, no conflict on the multiple. I help them connect with founders who might benefit from the same setup. Worth a brief chat?
LinkedIn DM · short form · talking points Quick note — you came up in a list of T&L founders I keep an eye on. I work with Next Mile (only-sellers M&A, no upfront cost). Not pitching, just opening a door if it's ever useful.
Voicemail · 20-second curiosity hook · talking points Hi [first name], it's Wally with Next Mile. We work exclusively with T&L founders. Reason for the call — I've got a quick question about [specific company context if known, otherwise: your business model]. No pitch, just a question. I'll try you back, or shoot me a reply by email if easier.

Format tip: these are talking points, not word-for-word scripts. Wally and Mike adapt to the contact's industry segment (asset-based vs. brokerage vs. 3PL) and to any specific signal in the contact record. Rigid scripts kill the operator voice the play depends on.

07Objection Handling

The pivots that don't shut the door.

Most cold-stage objections aren't "no" — they're "not yet" wearing different costumes. The pivot in every case is to lower commitment and keep optionality open.

I'm not selling.
Pivot: "Totally fair. Most of the founders I talk to aren't either, until something changes. The reason I reached out wasn't to ask if you're selling — it was to put a name in your back pocket for when the question comes up. Mind if I send you one piece of content a quarter, no follow-up?"
I already have an advisor.
Pivot: "Glad you do. Quick question — does your advisor represent both sides, or just sellers? The reason I ask: when the advisor has a buyer in the pocket, the multiple tends to land in a narrow band. We only represent sellers — different math. Happy to compare notes when you want a second opinion."
What's your fee?
Pivot: "Success-fee only. No retainer, no upfront cost. We get paid when you do, on terms we'd agree on if we got that far. But fees come after fit — let's see if there's even a reason to talk first."
Send me information.
Pivot: "Will do — I'll send one specific thing tied to where you are, not a brochure. What's most useful: how the process works end-to-end, or a recent deal in a business like yours?"
[Silence — no reply at all]
Pivot: after the 4-week cadence completes with no response, the contact downgrades to dormant and moves to the monthly educational email list. Door stays open; pressure removes.
Field validation pending Real objections from the 18 recorded calls will replace these starting points — particularly the language sellers actually use, which is usually less direct than the canonical versions above.
08Required Assets & Tools

What Wally needs to run this.

Every asset below is also tracked in the Stage 01 Asset Inventory with status and owner. The list here is the play-specific subset — what Wally actually opens, sends, or references when running the cold outbound sequence.

  • Cold Targeted named-account list (ZoomInfo + TIA + LinkedIn-sourced) Stage 01 In Progress
  • Cold outreach script · "operator who gets it" opener Stage 01 In Progress
  • LinkedIn DM script · value-first, no ask on first touch Stage 01 In Progress
  • Voicemail script · 20-second curiosity hook Stage 02 In Progress
  • "Get a Free Confidential Assessment" landing page Stage 01 In Progress
  • Multi-touch outreach cadence · email + LinkedIn + phone (4-wk) Stage 01 In Progress
  • Exit Readiness Library · Stage 4 Maturity content Stage 01 Need
  • Wally's operator-credibility one-pager (for "send me information") Need
  • "Only-sellers, success-fee only" battlecard (for "I already have an advisor") Need
  • Monthly educational email · the dormant-list fallback Stage 01 In Progress
Prototype note The remaining plays follow the same 8-element template. The pattern is validated when (a) Wally and Mike can read Cold Outbound and execute it without further explanation, (b) the call-analysis loop replaces the "Field validation pending" placeholders with seller-tested language, and (c) the Asset Inventory ownership column at Stage 01 reflects who actually owns each row. When those three conditions are met, building the remaining plays is a mechanical exercise.
Section 9
The Portal · inside Sellers

Two populations, one engine.

The Portal isn't a separate audience — it's two things the Sellers play does with sellers who aren't on the standard close path. Population A is the off-ramp from Stage 04 Evaluation: sellers who are real fits but whose numbers aren't where they need to be yet. Population B is a marketing motion: T&L operators (some already in our Sellers database, some not yet) who don't necessarily want to sell, but want a different view of their own data — the same operating data their TMS already gives them, shaped the way a buyer wants to see it. Pulling them into the Portal becomes a way to engage the database without selling them anything yet.

Population A · the off-ramp

Not yet ready — but real fits.

These are sellers who passed Stage 02 Engagement and entered Stage 04 Evaluation — the conversation revealed they want to sell, but the math doesn't yet support the multiple they need. Rather than lose them to "not yet" (and watch them dance with whoever calls next), the Portal keeps them inside the Next Mile relationship while they improve their numbers. Mike's proprietary analytics engine runs on their monthly TMS data and financials, showing them what's moving them toward sale-ready and what's holding them back. Next Mile doesn't get paid unless they sell — the Portal protects the funnel through the patient years.

What it runs on today.

Each portal company sends Mike a monthly file from their TMS plus end-of-month financials. Mike loads it into the proprietary analytics engine. 430+ reports update automatically: revenue, loads, profit, load types, expense trends, the standard T&L metrics — but shaped to show what a buyer would care about. The system calculates the implied multiple at today's performance and flags what's trending the wrong way.

Sellers see all the reports about their own business. Mike reviews each one and highlights what changed: where they're trending positive, where the expenses are moving the wrong way, what's standing between them and a higher multiple. The discipline keeps them engaged for the months or years until timing flips.

Who's here today.

The first paid Portal subscriber (Vache) signed at $500/mo on a 1-year minimum. The Engaged Not Ready-tier sellers (engaged-not-ready) are the next handoff cohort. Sutton Envoy has been in the captive holding pattern for 18+ months and is a candidate when the paid offer is productized.

The mechanic that matters: sellers feel they're getting a real operating service, not a parked-in-the-funnel feeling. The discipline of monthly data + monthly review is what keeps them present.

Population B · the marketing hook

A buyer's-eye view of their own data.

This is the second face of the Portal — the one that doesn't require the operator to be thinking about selling. Every T&L company already runs a TMS. The TMS gives them operating reports. But the operating reports answer the question "how is the business performing?" — they don't answer "what would a buyer see if they looked at this?" That's the Portal's unique angle: the same data, reshaped to show the things a buyer cares about (revenue mix, customer concentration, margin trends, EBITDA add-backs, the math that drives multiples). Many operators want this view even if selling is years away — or never. Inviting an operator into the Portal is a way to engage them without selling them anything.

Why this is a hook, not a sell.

The Portal subscription becomes a useful, paid operating product on its own merits. Operators who sign up get a view of their business they can't get from their TMS or their CPA. They get monthly reviews from someone who actually understands the M&A buyer side. They learn the language of the eventual exit conversation without committing to one. And they become a paying, engaged relationship that flows quarterly intelligence back to Next Mile.

Some of them eventually sell. Some never do. Both outcomes are good — the second one is a paying subscriber giving Next Mile a data feed and a relationship for years.

Why this is a database play.

Next Mile already has 2,700+ T&L contacts in the Sellers database. Most of them aren't ready to sell. Today, the only thing Marketing sends them is the monthly educational email — useful but easy to ignore. The Portal gives Marketing a real offer to make: "Want to see your business through a buyer's eyes? Try the Portal." That's a more interesting reason to open an email than "let's talk about selling someday."

This is the rationale for the new Portal Engagement · Sellers Database play in the play library above. It feeds Stage 03 Education — the holding pattern where most of the Sellers database currently sits.

What's open · product & pricing The fee schedule was already resolved (Mar 16): $500/mo entry-tier (Portal Growth Program), $1,000/mo mid-tier (consulting access), $4,000/mo full consulting + portal access. All consulting fees credit against the M&A success fee at close. What's open is productization for Population B specifically: which view of the data lands first, what the onboarding flow looks like, whether there's a 30-day free trial as the marketing conversion mechanic, and how the conflict-of-interest rules work between paid subscribers and the seller pipeline. Full pricing detail lives in Appendix · Subscription & M&A Fee Schedule.
How the two relate

The same product, two doors in.

Population A enters the Portal from Stage 04 (they tried to sell, weren't quite ready). Population B enters from Stage 03 (the marketing motion). They sit in the same product, see the same reports, and benefit from the same monthly review with Mike. The difference is the conversation around them: Population A is talking about a future sale; Population B is talking about a future possibility. Both are valuable. Both protect against losing a real-fit company to a less-thoughtful broker who calls them on the wrong day.

Entry point: Stage 04 → Portal.

Trigger: Evaluation surfaces real fit but wrong numbers. Mike has the conversation, presents the Portal as the alternative to "let's reconnect in a year," and the seller stays inside the firm rather than dancing with the next caller.

Entry point: Stage 03 → Portal.

Trigger: a Engaged Not Ready-tier seller (engaged-not-ready) or a Marketing-touched operator from the Sellers database opens a Portal invitation. The play is "see your business through a buyer's eyes" — no sale conversation required. Once inside, the relationship has months or years to mature.

Cold Outbound describes the motion. Next: what's actually running right now — the campaigns and assets currently in flight against that play.

Section 10
What's running right now

Campaigns & assets in flight.

The live executional layer. Which campaigns are deployed against which tiers, which assets exist, which are in draft, which are missing. The bi-weekly review reads this section to know what shipped, what stalled, and what needs ownership.

Tier Transitions

The triggers that move someone.

Transitions happen on signal, not calendar. HubSpot workflows watch for these signals and reassign lifecycle stage automatically.

  • Cold Targeted → Engaged Early trigger: Reply, call booked, or strong content engagement signal
  • Engaged Early → Engaged Ready trigger: Signed engagement letter
  • Engaged Ready → closed trigger: Closing
  • Any tier → Engaged Not Ready trigger: "Not now" response with positive sentiment
  • Engaged Not Ready → Engaged Early / Engaged Ready trigger: Inbound re-engagement (life event flipped, market moved, new readiness)
Sequencing

The rhythm per tier.

Cadence is what separates a generic outbound program from a high-trust seller engine. Each tier has its own rhythm. Mixing them dilutes signal in both directions.

Cold Targeted · Cold targeted
Four-touch intro · then quarterly value
4 touches over 4 weeks · pause · quarterly drops
  • Touch 1: Introduction (who we are, what we do, why different)
  • Touch 2: Story drop (one customer journey, paragraph form, link to full)
  • Touch 3: Process glimpse (how the Black Belt system works, what's different)
  • Touch 4: Soft ask (free confidential business assessment)
  • Then quarterly: comparables and stories
Engaged Early · Engaged early
Monthly nurture · personal at quarterly
Monthly · 4 content types rotating
  • Story (different one each month)
  • Comparable / deal flow update
  • Process insight or market color
  • Quarterly: personal check-in from Mike or Wally
  • Goal: be the first call when timing flips
Engaged Ready · Engaged ready
High-touch · personal · no automation
Weekly minimum · principal-led
  • Mike or Wally direct · weekly contact minimum
  • Calendar managed manually
  • No nurture sequences · relationships only
  • 1:1 Loom-style video where appropriate
  • Direct mail at signing or closing milestones
  • High-impact gifts at signing or closing
Engaged Not Ready · Engaged not ready
Quarterly value · annual personal
Light touch · portal as the soft handoff
  • Quarterly value drops (comparables, market color)
  • Annual personal check-in from Mike or Wally
  • Portal access offered as the soft handoff
  • Zero pressure, full education
  • Ready when they are
Calls to Action by Stage

What we ask, when.

CTAs escalate with engagement. The wrong ask at the wrong stage is more damaging than no ask at all.

Awareness · Cold Targeted
Read this story. Visit our site. Connect on LinkedIn.
Interest · Cold Targeted → Engaged Early
Get a free confidential business assessment. Schedule a 30-minute call.
Consideration · Engaged Early
Walk through your numbers with us. See what your business looks like through a buyer's lens.
Decision · Engaged Early → Engaged Ready
Sign engagement. Begin data prep.
Holding · Engaged Not Ready
Join the portal. Stay informed.
Channel Mix

Where we reach the seller.

Email is primary across all tiers. Other channels layer in based on tier signal and intimacy. The richer the relationship, the more channels are unlocked.

Channel Cold Targeted Engaged Early Engaged Ready Engaged Not Ready Use case
Email Primary across all tiers. Sequenced for Cold Targeted and Engaged Early; manual for Engaged Ready; quarterly for Engaged Not Ready.
LinkedIn · Awareness, light engagement, connection requests for Cold Targeted. Continued engagement for Engaged Early/Engaged Ready.
Phone · · Engaged Early and Engaged Ready personal contact. Mike or Wally direct.
Direct mail · · Reserved for Engaged Ready (about to sign) and high-priority Engaged Early.
High-impact gifts · · · Engaged Ready only. At signing or closing milestones.
Video (1:1 Loom) · · Personal Loom-style for Engaged Early and Engaged Ready. Concrete and specific to their business.
Events / dinners · TIA, regional industry events, hosted dinners. Annual touch even for Engaged Not Ready.
Webinars / roundtables · Cold Targeted and Engaged Early educational topics. Engaged Not Ready as readiness building.
LinkedIn · Operator Voice

Where Mike and Wally show up as themselves.

LinkedIn is the deepest channel investment in the engine after email. Mike and Wally post as founders, not as a corporate brand. Operator-to-operator voice is what cuts through the noise of M&A solicitors who clearly don't know the industry.

What Mike and Wally post.

Goal is recognition before the cold sequence ever lands. By the time a Cold Targeted target sees Touch 1, they should already have crossed paths with the operator voice on LinkedIn at least once.

  • Customer story postsOne post per alumni interview, distributed weekly. Lead with the operator's words, not Next Mile's. Doug, Ross, Wally, Roger, Dan, Carol on rotation.
  • Comparables drops"What just sold in T&L" anonymized monthly. The same content that energizes Buyers and gives COIs something to forward.
  • Process glimpsesBehind-the-scenes language. Data room prep, the night-before-meeting prep dinner Roger described, the "abnormal ask" library.
  • Engagement, not broadcastMike and Wally comment on prospects' posts before ever sending a connection request. Light, genuine, frequent.
  • Sales Navigator for Cold Targeted SellersTargeted connection requests for Cold Targeted seller founders by ZoomInfo profile match. Note in the request references shared experience, not the pitch.
  • Customer co-postsWhere alumni opt in, repost their reflections (with permission) and tag. Doug and Wally are likely candidates.
Programmatic & Targeted Digital

Surround sound for engaged accounts.

Targeted programmatic isn't a brand awareness budget. It's a precision tool for keeping warm contacts and named accounts surrounded with Next Mile presence so the next direct touch lands in a recognized name, not a cold one.

How programmatic earns its place.

Audiences are built tier by tier. Spend gates to engaged-only segments. Stale ZoomInfo lists never receive paid ad treatment. The cost goes to people we already know are warming, not to confirming the cold path doesn't work.

  • Cold Targeted · LinkedIn matchProfile-match audiences built from ZoomInfo and TIA attendee data. Light reach, founder voices, no hard sell. Goal: name recognition before Touch 1.
  • Engaged Early · named-account displayIP-targeted display retargeting on named accounts. Story-led creative. Emphasis: customer journeys, not brand impressions.
  • Engaged Ready · surround soundLinkedIn matched audiences plus IP retargeting on the active deal contacts. Reinforces Next Mile presence during the highest-stakes weeks.
  • Engaged Not Ready · portal campaignRetargeting that points to free portal access. Permission marketing posture. Useful, not pushy.
  • Website retargetingAnyone who hits the customer-journey pages, comparables page, or portal landing gets light retargeting. Spend gated to behavior, not list.
  • Sequencing ruleNo paid amplification of an asset until it has organic traction. The signal that an asset is ready for paid is engagement on Mike or Wally's organic post.
Content Backbone · John's Exit Readiness Library

The library is the campaign content.

John Knicely's Resources Page on nextmilema.com is the campaign content backbone. Five categories, ~28 titles. Each campaign email is essentially a teaser for one library piece + a CTA. Standard CTA across the engine: "Schedule a Confidential Conversation." See the companion Campaign Flowchart document for which title lands at which touch in each tier.

Real Client Stories · 6 titles
One per alumni interview. "How Dan Krivickas Compressed His Timeline" · "Why Roger & Deanie Chose to Have 'Someone on Their Team'" · "What Ross Learned Selling a 13-Terminal, 800-Employee Operation" · "Carol's Story: Finding Marketability Where She Thought There Was None" · "Doug's Four-Year Journey: From Partner Death to Successful Close" · "Wally's Path: From Founder to Managing Partner"
Source: 6 alumni interviews · drafted
Exit Readiness & Planning · 5 titles
"Is Your Transportation Business Ready to Sell?" · "Timeline: Planning Your Exit 12-24 Months Out" · "Common M&A Pitfalls for First-Time Sellers" · "What Makes a Transportation Business Marketable?" · "How to Strengthen Your Business Before Going to Market"
Status: John producing
Understanding the Process · 5 titles
"What to Expect When Selling Your Transportation Business" · "How Long Does It Really Take to Sell a Logistics Business?" · "The Role of an M&A Advisor: What They Actually Do" · "Due Diligence Explained: What Buyers Will Ask For" · "From First Call to Close: The M&A Timeline"
Status: John producing
Industry-Specific Insights · 6 titles
"How Capacity Fluctuations Impact Transportation Valuations" · "Why Customer Concentration Matters to Buyers" · "Asset-Based vs. Non-Asset: What Buyers Really Care About" · "The Hidden Value in Your Carrier Network" · "How Current Freight Market Conditions Affect Exit Timing" · "Insurance Costs and Nuclear Verdicts: What It Means for Your Valuation"
Status: John producing · also feeds Buyers play
Deal Structure & Terms · 6 titles
"Understanding Earnouts: Pros, Cons, and What Can Go Wrong" · "Seller-Side vs. Buyer-Side Representation: What's the Difference?" · "What's in a Letter of Intent (LOI)?" · "Purchase Agreement Terms Every Seller Should Understand" · "How to Evaluate Multiple Offers (It's Not Just About the Price)" · "Transition Requirements: What Buyers Expect Post-Close"
Status: John producing · also feeds COIs play
Comparables · "What just sold"
Not a library category. Recurring monthly artifact built from active deal flow. Same content reused across Sellers, COIs, Buyers, Portal. Highest-leverage content investment in the engine.
Status: cadence to define · cross-play asset
Sample CIM and data room walk-through
"Show, don't tell" asset for Engaged Early sellers kicking tires. What buyers see. Sanitized template based on past deals. Lives in the Portal library.
Status: TBD
Sample buyer match output
What the system produces when a seller's profile is run through the 300+ database. Tangible artifact that previews the value. Lives in the Portal library.
Status: TBD

Standard CTA across the engine: Every campaign email and library piece ends with "Schedule a Confidential Conversation." Supporting line per John's copy: "No upfront fees. No hard sell. Just straight talk from people who've guided 90+ successful exits."

Campaign Flow · Sellers

Every touch named to a library title.

Each tier's full sequence: who's in it, the touches, the channels, the content angles, and the exit triggers. Every email content slot points to a specific blog title from John's Exit Readiness Library. Standard CTA: "Schedule a Confidential Conversation."

Cold Targeted

Targeted Cold

GOAL: Earn the first reply. Qualify into Engaged Early or out.

SOURCE: ZoomInfo profile match · TIA member directory · LinkedIn network

PRE-WORK
LinkedIn
Awareness
Mike/Wally posts · story-led · recognition before T1
WK 1
Email · Touch 1
Introduction
"Seller-Side vs. Buyer-Side Representation: What's the Difference?"
CTA: Schedule a Confidential Conversation
WK 2
Email · Touch 2
Story drop
"Why Roger & Deanie Chose to Have 'Someone on Their Team'" (rotation)
CTA: Read full story
WK 3
Email · Touch 3
Process glimpse
"What to Expect When Selling Your Transportation Business"
CTA: Visit Resources page
WK 4
Email · Touch 4
Soft ask
"Is Your Transportation Business Ready to Sell?" + free assessment
CTA: Schedule a Confidential Conversation
PAUSE
8–10 weeks
No contact
Programmatic continues at low touch
Q+1
Email · Quarterly
Value drop
Comparable OR new alumni story (rotation)
CTA: Schedule a Confidential Conversation
Running in parallel · digital layer
LinkedIn matched audienceLight reach · founder voice creative · story-led posts. Goal: name recognition before T1 lands.
Sales Navigator connectMike/Wally personally · note refs shared experience, not pitch.
Website retargetingIf they hit a story page or Resources page · light follow with comparables creative.
Exit triggers · what moves them out of Cold Targeted
→ Engaged EarlyReply · calendar booked · multiple opens + clickthrough on story page
→ Engaged Not Ready"Not now" with positive sentiment
→ ArchiveHard bounce · unsubscribe · 12 mo no engagement
Library titles in rotation for Cold Targeted
  • Differentiator (T1): "Seller-Side vs. Buyer-Side Representation: What's the Difference?" anchors operator-credibility frame.
  • Story drops (T2): Six "Real Client Stories" titles rotate one per cycle. Roger/Deanie, Doug, Ross, Wally, Dan K, Carol.
  • Process glimpses (T3): "What to Expect" entry point. Quarterly variants pull from "From First Call to Close" and "How Long Does It Really Take."
  • Readiness ask (T4): "Is Your Transportation Business Ready to Sell?" — most natural tee-up to the free assessment.
  • Quarterly drops: Pull from any educational category based on what's most timely. Comparables ("what just sold") run on the same cadence.
Engaged Early

Engaged Early

GOAL: Deepen relationship. Qualify timing. Move to Engaged Ready.

SOURCE: Cold Targeted graduates · COI referrals · TIA replies · inbound

MONTH 1
Email
Story
"Doug's Four-Year Journey: From Partner Death to Successful Close"
MONTH 2
Email
Pitfalls
"Common M&A Pitfalls for First-Time Sellers"
CTA: Schedule a Confidential Conversation
MONTH 3
Email
Industry insight
"Insurance Costs and Nuclear Verdicts: What It Means for Your Valuation"
QUARTERLY
Phone / video
Personal
Mike or Wally direct · tailored, brief · not a pitch
MONTH 5
Email
Story
"What Ross Learned Selling a 13-Terminal, 800-Employee Operation"
MONTH 6
Email
Marketability
"What Makes a Transportation Business Marketable?"
CTA: Schedule a Confidential Conversation
MONTH 7+
Email
Rotation
Cycle continues across all 5 categories
Running in parallel · digital layer
IP-targeted displayNamed accounts · story-led creative · not brand impressions.
LinkedIn engagement loopMike/Wally comment on prospect's posts · mutual visibility maintained between drips.
1:1 Loom videoAny moment that warrants it · specific to their business · tailored insight.
Exit triggers
→ Engaged ReadySigned engagement letter
→ Engaged Not Ready"Not now" with positive sentiment
→ Cold TargetedUnresponsive 6+ months · reset cadence
Library titles in rotation for Engaged Early
  • Real Client Stories (every other month): All 6 alumni titles rotate. Doug → Ross → Wally → Roger/Deanie → Dan K → Carol.
  • Exit Readiness & Planning: "Common M&A Pitfalls" · "What Makes a Transportation Business Marketable?" · "How to Strengthen Your Business Before Going to Market" · "Timeline: 12-24 Months Out"
  • Industry-Specific Insights: "Insurance Costs and Nuclear Verdicts" · "Why Customer Concentration Matters to Buyers" · "The Hidden Value in Your Carrier Network" · "How Current Freight Market Conditions Affect Exit Timing"
  • Deal Structure & Terms: "Understanding Earnouts" (Roger & Deanie's earnout angle) · "How to Evaluate Multiple Offers" (Dan K's cultural fit) · "What's in a Letter of Intent?"
  • Process (rotates in): "Due Diligence Explained: What Buyers Will Ask For" · "The Role of an M&A Advisor: What They Actually Do"
Engaged Ready

Engaged and Ready

GOAL: Sign engagement. Run the process. Close the deal.

SOURCE: Engaged Early graduates · direct inbound from network · alumni references

PHASE 1
Pre-sign
Numbers walk-through
"Due Diligence Explained" + buyer's-lens preview · Mike/Wally direct
PHASE 2
Signing
Engagement letter
Direct mail + gift · begin data prep
PHASE 3
Process
Data room build
CIM · sample buyer match output · "show don't tell"
PHASE 4
To market
Buyer outreach
Mgmt presentations · night-before prep dinner (Roger's framing)
PHASE 5
Close
LOI · diligence
"What's in an LOI?" reference · abnormal-ask guard · closing gift
Continuous · principal-led
Mike or Wally weekly minimumPhone · text · brief email · whatever the moment calls for.
1:1 Loom videoAt high-stress moments · specific to their deal · never templated.
Programmatic surroundIP retargeting on deal contacts · LinkedIn matched for high-stakes weeks.
Exit triggers
→ Closed alumniDeal closes · case study · Engaged Not Ready advocate role
→ Engaged Early re-entryDeal falls through · resume nurture cadence
→ Engaged Not Ready archiveWalks from process with positive sentiment
Library titles used during Engaged Ready
  • Pre-sign: "Due Diligence Explained: What Buyers Will Ask For" + "From First Call to Close: The M&A Timeline" set expectations.
  • Process: "Purchase Agreement Terms Every Seller Should Understand" demystifies legal docs.
  • To market: "How to Evaluate Multiple Offers (It's Not Just About the Price)" — Dan K's cultural-fit story makes this concrete.
  • Close: "Understanding Earnouts" (Roger & Deanie's experience) + "Transition Requirements: What Buyers Expect Post-Close" (Carol's stay-through experience).
  • Continuous reference: Mike/Wally point clients to specific library pieces during the process. Less material to write fresh; more time on the deal.
Engaged Not Ready

Engaged But Not Ready

GOAL: Stay top of mind. Route to portal. Capture when timing flips.

SOURCE: Cold Targeted/Engaged Early/Engaged Ready "not now" · past clients · friends & family · alumni

Q1
Email · quarterly
Comparable
"What's selling in your segment" · monthly comparables digest
Q2
Email · quarterly
Market color
"How Current Freight Market Conditions Affect Exit Timing"
CTA: Visit Resources page
Q3
Email · quarterly
Story rotation
Alumni they haven't seen yet (long rotation across all 6)
Q4 · ANNUAL
Phone
Personal check-in
Mike or Wally · no pitch · genuine
SOFT HANDOFF
→ Portal
Free portal access
Education library + comparables + readiness assessment
CTA: Activate portal access
Running in parallel · light touch
Light retargetingPoints to portal landing · "useful, not pushy" posture · never a hard ask.
Portal engagement trackingLogin frequency · assessment activity · comparable open rate.
LinkedIn light visibilityContinued comment engagement on alumni posts they follow.
Exit triggers
→ Engaged Early/Engaged ReadyInbound re-engagement · life event flipped
→ Engaged Early alertPortal engagement spike · HubSpot notifies Mike
→ Archive3+ years no engagement of any kind
Library titles in rotation for Engaged Not Ready
  • Quarterly market color: "How Current Freight Market Conditions Affect Exit Timing" is the recurring frame; sub-rotates with "How Capacity Fluctuations Impact Transportation Valuations."
  • Readiness building: "Timeline: Planning Your Exit 12-24 Months Out" + "How to Strengthen Your Business Before Going to Market" — useful to a Engaged Not Ready years out from event.
  • Story long rotation: Each Engaged Not Ready sees one alumni story per year. Long cycle, deliberately not repetitive.
  • Portal handoff: "Is Your Transportation Business Ready to Sell?" is the readiness-assessment entry point inside the portal.

Last: how we know it's working. Budget, KPIs, and the alumni proof that grounds every claim.

Section 11
What it costs, how we measure

Budget & KPIs.

What the Sellers play costs to run, what we measure to know it's working, and the leading indicators that tell us when something needs attention before pipeline shows it.

Budget & KPIs

What it costs, what we measure.

Budget and KPI content currently lives interleaved with VOC in the original layout. As we mature the document, this section will hold the dollar-level investment and the leading indicators we watch.

COIs · Activating · first COI-sourced deal in motion

COIs.

Centers of Influence · referral engine into Sellers
3
Audience tiers
Targeted · In Conversation · Engaged
20%
Year-1 referral
fee on closed deals
5
Active partnerships
in motion · May 2026
The Single Most Important Message

"One referral a year beats a thousand cold emails."

A motivated attorney, CPA, or wealth manager who sends one qualified referral a year is worth more than a thousand cold emails. The 20% referral fee on closed transactions is the rational hook. Making them look smart in front of their client is the emotional one. Our content has to do both.

Activated at TIA Capital Ideas · Apr 15, 2026
Audience · Centers of Influence

COIs · the partnership engine.

COIs are the relationships that produce warm seller introductions and validate Next Mile to people who otherwise would have ignored the cold outreach. This is the partnership play — different motion from Sellers, longer cadence, peer-to-peer voice. Five tiers (First-to-Know · Active Referrers · Validators · Buyer-side · Long-tail), 36 mapped today, 20% Year-1 / 10% Year-2 referral economics. Below is the story behind this play.

Section 1
Who they are

Three tiers of partnership.

COIs aren't a uniform group. They're three operational tiers (Targeted · In Conversation · Engaged) layered on top of the five COI archetypes (First-to-Know · Active Referrers · Validators · Buyer-side · Long-tail) defined in the Sellers play. The operational tier tells you the cadence; the archetype tells you what they care about.

Why COIs

The signal before the signal.

By the time a seller is publicly considering a sale, the conversation is already crowded. By the time they're contractually committed to an advisor, it's too late. COIs see the signal months earlier, when the owner is still talking privately to the people they trust most: their attorney, their CPA, their banker, their insurance broker.

Wally's framing.

"I want COIs to feel excited about the ability of what we can do for their clients, and the fact that they can make 20% of the fee could be significant."

Wally Brauer · Managing Partner · COI Program design call · Mar 16, 2026

The leverage math.

One closed seller deal pays a single COI hundreds of thousands of dollars on the 20% economics. That's the rational reason a lawyer or wealth manager sends a referral. The emotional reason is harder and more durable: they want to look smart in front of the client they referred. Our content needs to make them look smart when they share it.

This is why content built for COIs cannot feel like marketing. It has to be useful for their client conversation, framed for their professional voice, and shareable without modification.

Two Outcomes

What this play produces.

The COI play has two parallel outcomes. Both feed the seller play directly.

Outcome 1 · Referrals.

Direct seller referrals from COIs. Tagged in HubSpot, attributed to the referring COI, run through the same Sellers play tier mechanics from Engaged Early onward (because COI referrals come pre-warmed; they almost never start at Cold Targeted).

Outcome 2 · Validation.

Even when a COI doesn't have a referral to send today, their awareness of Next Mile validates the firm to their network. When a Next Mile name surfaces in a different conversation, the COI's recognition becomes social proof.

Status

Where the play stands today.

Build sequencing recommendation: lock down COI play structure within the next 30 days. It's the highest-leverage source of seller pipeline.

01
Tier Structure DefinedTargeted · In Conversation · Engaged
✓ Complete
02
Category Map (TIA)36 vendors, 5 tiers across insurance/finance/staffing/data/freight tech/TMS
✓ Complete
03
Category Prioritization ExerciseRank historical referral hit rate by category
Open · run once with Mike
04
Fee Economics20% Y1 / 10% Y2 · 6-mo window · portal exception
✓ Complete
05
Referral AgreementDrafts in flight · owner: Dan
In Approval
06
Gifting ProtocolItem, budget, fulfillment owner
Define · TBD owner
07
HubSpot AttributionCOI source tagging, closed-loop reporting
Pending Sales build
08
COI-Specific Content"How the 20% works" + "What a good referral looks like"
Not started
Active COI Partnerships

Five COIs in motion.

The post-TIA wave produced named partnerships, not just business cards. These are the COIs currently in active conversation with Mike and Wally as of the May 12 leadership call. Each carries an owner, a next step, and a target outcome. The first COI-sourced deal (FreshX) is already traveling through the engine.

Howden Group
Tom Moran · Tom O'Donnell (boss)
Tier 1 · Insurance Broker

Howden was the TIA partner that hosted the network night where Craig Helmrich was met. Mike + Wally meeting was originally scheduled for the prior Thursday, pushed by Tom O'Donnell's schedule. Now confirmed for May 14, 2026.

Scheduled
Next: May 14 meeting with Mike, Wally + Howden leadership.
Cottingham
Transportation Attorney
Tier 1 · Legal

Connected to Chris Vogel. Met during the TIA window. Meeting agreed but deferred until Mike returns from Italy. Funny email exchanges back and forth set the tone for the June conversation.

Scheduled
Next: June meeting post-Italy.

Name note: Cottingham (attorney) is not Cottingham & Butler (insurance broker). Two different organizations. Caught on the May 12 call. Worth disambiguating in HubSpot.

Cottingham & Butler
Insurance Broker
Tier 1 · Insurance

Big insurance broker. Meeting agreed but pushed to June when Mike is back from Italy.

Scheduled
Next: June meeting post-Italy.
Roanoke Insurance
Tier 1 contact + boss in copy
Tier 1 · Insurance

Big insurance broker. Both the direct contact and their boss in copy on the email exchange. Both agreed to a meeting. Pre-existing Roanoke names were in the TIA priority list (President Karen Rzeszutko + VP David Pasco).

Scheduled
Next: Meeting calendar coordination.
Where FreshX Could Land

Two buyer destinations in Mike's database.

The first COI-sourced deal needs a buyer-side endpoint. Two named buyers in Mike's database have stated tech-acquisition appetite. Both are active conversations with Mike as of May 12.

Kevin Nadeau
Wants to buy all the technology companies that exist. Mike had a 4:30 PM call with him on May 12. Discussion items: "COI opportunities in general, between us."
Strong fit for FreshX (tech-producer-becoming-4PL).
10 Street
Wants to buy technology developers. Mike had a separate call queued for after the May 12 leadership meeting.
Possible alternative for FreshX or others in the same lane.
The Core Principle

COIs aren't lead sources. They're validation engines.

When a COI refers a brokerage owner to Next Mile, they're putting their own reputation on the line. The process has to earn and protect that trust at every stage. This reframe matters: an SDR-style "lead source" mindset will erode COI relationships. A "validation engine" mindset compounds them.

The 12–24 month signal.

Insurance brokers, payment platforms, and TMS vendors often know who is thinking about selling 12 to 24 months before a deal surfaces. They see partnership stress in the buy-sell renewal. They see cash-flow pressure in factoring activity. They see growth ceilings in TMS volume plateaus.

Building COI relationships in those categories creates an early-warning pipeline — referrals at the inflection point, not at the moment the seller has already decided to go to market.

Next Mile as the strategy node.

The COI ecosystem positions Next Mile as the M&A strategy node in a trusted advisor network: Insurance (advises on risk, sees exit prep early) · Payments & Finance (factoring with deep relationships) · Technology / TMS (embedded in daily ops of growth-stage brokers) · Staffing & Outsourcing (sees scaling struggles) · Freight Tech / AI (next-gen broker data) · Data & Compliance (broad visibility into health).

The aspirational long-term position: "the firm every insurance broker, TMS vendor, and staffing company calls when their client asks what should I do with my business?"

The Value Exchange · three pieces.

Economic Incentive
+20% Referral Fee
Year 1 on every closed deal. Sized to be meaningful (six figures on a typical engagement), not symbolic. See Appendix · COI Referral Fee Structure.
Process Transparency
Structured Updates
COIs get visibility into where their referrals are in the process. Reputation protection comes from knowing their client is in good hands, not from blind handoff.
Outcome
Client Success
The COI's client walks away with a better outcome than they could have produced on their own. The COI keeps the relationship and becomes a stronger trusted advisor.

The Flywheel Effect.

01
Closed Deal
02
Validate Trust
03
Pay Referral Fee
04
"Who's Next?" Intro

Every closed deal that came through a COI must complete this loop. Step 04 is the most overlooked: asking, in the right way at the right moment, who else in the COI's book is in a similar conversation. The fee creates the rational reason to keep referring; the client success creates the emotional one.

What's Inside

The COIs play in operational order.

From strategy through to running campaigns. The COI engine that feeds Sellers, mapped end-to-end.

01
OverviewWhy COIs, two outcomes, status, active partnerships, the core principle
✓ Complete
02
Triggers & AudienceThree tiers, category prioritization, TIA-mapped 5-tier vendor map
✓ Complete
03
Messages & NarrativeThe 30-Second Conversation script
✓ Complete
04
ConversationPartnership-fit dive, referral follow-up, first-referral handling, post-close loop
✓ Complete
05
Network & COIsFor COIs, the network IS the play — content sits in Overview + Triggers
Awaiting · may always be empty (network = play)
06
Campaigns & AssetsTIA floor sourcing + tactical play, sequencing, CTAs, referral economics, tracking, channel mix, LinkedIn, programmatic, content needs, campaign flow
✓ Complete
07
Budget & VOCVoice of the Customer · COI angle (Budget pending)
Partial · VOC present, Budget pending

Now that we know who they are, what they actually said — alumni and active partners in their own words.

Section 2
What we heard them say

Voice of the partner.

Verbatim quotes from COI partners and alumni about what the relationship has to be for it to work. The pattern: peer respect, business reciprocity, and absolutely no transactional pressure on the first three touches.

Voice of the Customer · COI angle

The quotes that make the case.

Verbatim. Selected for the COI conversation. Testimonials about advisor quality and process integrity travel well in a referral context.

"For us, it was all about being able to trust the person representing us. And Mike and Black Belt have the utmost integrity. They deal in transparency and honesty, and they are absolutely an advocate for you."

Dan Krivickas · American Group · attorneys/CPAs travel well with this

"Mike's background really, really struck me as somebody that was in the trenches within the industry also. Whereas many of these M&A firms, they don't know anything about the industry."

Wally Brauer · Founder, Freight Solutions · differentiator a COI can articulate

"It was so one-on-one with Black Belt and we felt very comfortable with him and also just in the process."

Carol Bennett · Carrier Services · contrast with template-based competitors

"I would absolutely advocate that you consider Black Belt. In fact, not even just consider them, just go with them."

Dan Krivickas · American Group · the strongest endorsement available

"I want COIs to feel excited about the ability of what we can do for their clients, and the fact that they can make 20% of the fee could be significant."

Wally Brauer · Managing Partner · COI Program design call · Mar 16, 2026

Those voices tell us what the relationship has to feel like. Next: where COIs are in their own journey when they become useful to us.

Section 3
Where they are in their journey

The COI lifecycle.

COIs progress from Targeted (we know them, they don't know us yet) through In Conversation (we've had a structured talk) to Engaged (they're actively referring). The triggers that move someone between tiers — and the signals we watch for in our own database to spot a COI emerging from a Seller relationship.

Three Tiers

Where every COI lands.

COI engagement state matters more than COI category. A Tier Engaged insurance broker who sends two referrals a year is worth more than ten Tier Targeted wealth managers we haven't met.

Targeted
Targeted
Targeted

COIs we have identified but never had a real conversation with. Sourced from TIA attendee lists, industry events, profile-match research.

GOAL: First substantive conversation. Move to In Conversation.
In Conversation
Conversation
Identified Plus Conversation

COIs we have spoken with at least once. They know we exist but haven't sent anything yet. The longest tier mathematically; warming a In Conversation into a Engaged is the multi-month grind.

GOAL: First referral. Move to Engaged.
Engaged
Engaged
Engaged

COIs who have sent a referral, attended an event, or are actively partnering. These get elevated personal contact, real-time updates on their referrals' progress, and recognition.

GOAL: Multiple referrals per year. Hall-of-fame relationship.
Category Prioritization

Not all categories convert equally.

Worth running a one-time exercise with Mike to rank categories by historical referral hit rate. Until that's done, this is the working hypothesis. Weight content frequency and touch investment by category fit.

Category Why they see signal Weight
M&A attorneys Owner already exploring sale, picking advisors. Closest to the deal. High
Tax accountants & CPAs Year-end conversations surface estate planning, succession, "what if." First to know about lifestyle pressures. High
Wealth managers / financial advisors Personal financial planning conversations include exit timing. Owner trusts them with the lifestyle question. High
Fractional CFOs Often the first hire when an owner starts thinking about scaling or selling. High signal density. Med-High
Insurance brokers (T&L specialists) Annual renewal conversations are when "what's next" comes up. T&L specialty is critical. Med-High
Industry consultants Operational improvement work often precedes a sale. Visible to readiness signal. Med
Banking relationships (commercial lenders) Loan reviews and financing decisions surface succession plans. Long-term relationships. Med
Adjacent service providers (factoring, equipment finance) Operational health visibility. Tier-three signal. Low-Med
TIA-Mapped COIs · 5 Tier Vendor Map

36 vendors. Five priority bands.

The TIA campaign mapped 36 specific vendors across 5 tiers. Floor strategy was Day 1 = Tier 1 + 2 (20 meetings), Day 2 = Tier 3–5 (16 meetings). These slot into the audience tiers above based on conversation depth coming out of TIA.

Tier 1
10 vendors · MUST-MEET · highest referral value
Insurance & Finance
Signal: First to know when an owner is considering an exit. Insurance and finance partners renew annually; sale conversations surface in those reviews.
Conversation Angle"You see the financial health and risk profile of these brokerages before anyone else. We help them plan the strategic exit that maximizes that value. It would be great to compare notes on who is getting ready for that next step."
Reliance Partners · Roanoke Insurance · Gallagher · PFA Transportation · LogistIQ · Avalon Risk · Verisk CargoNet · Gulf Coast Business Credit · Triumph · Relay Payments
Tier 2
5 vendors · SHOULD-MEET · operational signal
Staffing, BPO & Operations
Signal: See scaling struggles before anyone else. Leading indicator of an eventual sale.
Conversation Angle"We work with brokerage owners who are scaling fast and thinking about what's next — whether that's a strategic partnership, acquisition, or eventual exit. Your clients are probably in that same conversation."
Lean Solutions Group · My Freight Staff · The DDC Group · CS Recruiting · Easy Metrics
Tier 3
5 vendors · SHOULD-MEET · data signal
Data, Visibility & Compliance
Signal: Visibility platforms and compliance vendors see the operational data that buyers will eventually want.
Conversation Angle"Your data gives you a unique view on brokerage health. We're interested in the companies that are managing risk well and growing volume. Let's compare notes on the market leaders."
SMC3 · Transflo · Trimble · Overhaul · Carrier Assure
Tier 4
6 vendors · SHOULD-MEET · innovation adjacency
Freight Tech & AI Automation
Signal: Adoption signal. Owners modernizing for sale often surface here first.
Conversation Angle"You're capturing the most forward-thinking brokerages. We're looking for exactly those kinds of tech-enabled operators for our pipeline. Let's discuss who is ready for scale."
Greenscreens.ai · Highway · Parade · Levity · Augmented Technologies · HappyRobot
Tier 5
10 vendors · LOWEST PRIORITY ⚠ · IP risk
TMS & Core Technology
Signal: IP risk is real. Approach cautiously. Do not share portal methodology. Useful for general industry intel only.
Conversation Angle · Use with Caution"Your platform is the operating system for these brokerages. You see the data — you know who is scaling efficiently and who is hitting a ceiling. We help those owners unlock that next stage of value." Caveat: If the conversation deepens, do not share Next Mile portal methodology. TMS vendors map our process to product features and we lose the asymmetry.
McLeod · DAT · Truckstop · Descartes · PCS · Tai · Rose Rocket · Turvo · Revenova · Blue Yonder

The journey gives us the when. The narrative below gives us the how — what we say at each tier.

Section 4
What we say to them

Peer-to-peer, not sales-to-prospect.

COIs don't want to be sold. They want to be respected as peers who happen to have aligned interests. The narrative arc is built around how Next Mile partners with their existing client base, not how Next Mile recruits new business through them.

The 30-Second Conversation

One repeatable script. Strategic, not salesy.

The opener Wally and Mike used at TIA Booth #218 — and the one any team member should use the next time they're at a COI event or meeting. It works because it leads with value to the COI's client, doesn't ask for anything, and qualifies the relationship through the COI's response.

"We work with brokerage owners who are preparing for growth or an eventual exit — usually 2 to 5 years out. A lot of your clients are probably in that same conversation right now. It would be great to compare notes and see if there's a way we can help each other."

The 30-second opener · TIA Floor Game Plan

Why it works.

  • Leads with value. You help their clients, not just your pipeline.
  • Non-threatening. No hard ask, just a conversation.
  • Creates reciprocity. You're offering to refer, not just receive.
  • Qualifies naturally. The COI's response tells you how warm the relationship is.

The follow-up ask.

The script earns the right to a small structured commitment. The follow-up:

"Would it make sense to grab 20 minutes after the show to talk about what a referral relationship could look like?"

The follow-up commit · TIA Floor Game Plan

The alternative floor opener.

For vendor conversations where the COI is mid-sentence about a client situation, this opener inverts the ask — pulling the referral signal out of the conversation directly:

"We help brokerage owners figure out if a sale, acquisition, or partnership is the right next move — and then we run the process. Who in your book is asking those questions?"

Alternate opener · used to harvest active referral signals on the floor

What to listen for on the floor.

Four phrases that mean a referral signal is live in the conversation. When a COI says any of these, the next response is a structured ask:

  • "We have a client who..." → ask "What stage are they at?"
  • "They've been with us for 10+ years" → long-tenure clients are often in the exit window.
  • "They're trying to figure out what's next" → classic Stage 5 / Exit Window language.
  • "They want to grow but can't get there alone" → capital or capability gap. Acquisition or sale both apply.

That's the story. Now: how it plays out in an actual COI conversation.

Section 5
How the conversation goes

The 30-second opener.

COI conversations have a different rhythm than Seller conversations. There's less urgency, more long-game thinking. The opener earns 20 minutes; the 20 minutes earns the right to discuss specifics; specifics earn the referral agreement.

How the COI Conversation Goes

After the 30-second hook lands, what happens next?

The 30-Second Conversation (Messages & Narrative) is the opener. This is what comes after. The deeper-dive agenda that turns polite interest into a structured referral relationship. Wally's operator instinct drives this today; the artifacts surfacing below are how that instinct gets documented as it scales.

01
Hook to deeper dive · Stage 02 Engagement

The 30-second conversation produced interest. The next conversation is the partnership-fit dive. Open question: "Tell me about how your clients typically navigate the exit conversation today. What do they wish was different?" The COI does most of the talking. Wally and Mike listen for: client volume, client size, current exit-advisor relationships (or lack), and whether the COI has agency to refer.

02
Partnership economics · made explicit

Referral economics (resolved March 16, 2026): 20% of fees Year 1, 10% Year 2. The economics aren't hidden. Craig Helmrich (Helmrich Law) understood this on the first conversation. Wally: "He has brought deals to M&A firms that have just shipped the bed. He was looking to partner with an M&A firm. So this is just, it's perfect."

03
First referral · the test

The relationship gets real when the COI sends the first referral. FreshX (Helmrich-sourced) is now traveling through the engine — going either to Kevin Nadeau or 10 Street on the buy side. How the first referral is handled determines whether COI #2 ever lands.

04
Closing the loop · Stage 11 Referral

The post-close conversation. "Here's what just closed; here's what we learned; thank you for the trust." This is what makes referrals 2-10 land easier than referral 1. Carol Bennett: "You can rely on that and know that it's a safe space because he's always got your back."

Now: where COIs actually gather, and where partnerships get made.

Section 6
Where they hang out

The rooms COIs are already in.

For COIs, the rooms matter even more than for Sellers. The peer-validation channel runs through industry associations, vendor conferences, and the trust networks built over decades of operating relationships.

Awaiting · The network IS the play

For COIs, this sub-tab may always sit empty.

Sellers and Buyers use this sub-tab to describe where their audience gathers and who whispers in their ear. For COIs, the network IS the play. The audience, gathering places, and tier framework all live in Triggers & Audience. The active partnerships sit in Overview. This sub-tab is preserved for structural symmetry with the other plays, not because it carries unique content.

Knowing where they are points to the named motions we run to reach them.

Section 7
The plays we run

Named COI motions · awaiting call analysis.

Below are the named motions the COI play will run, organized by which Sellers-play stage they feed. Cold Outbound for Sellers is fully built as the prototype; the COI plays are placeholder cards until the call analysis loop (Wally's and Mike's recorded calls) supplies the discovery questions, scripts, and objection handling. Once analyzed, each card expands into the same 8-element format as Cold Outbound.

Feeds Sellers · Stage 01 Prospecting
Pending · call analysis

COI Outreach · Targeted

Quarterly content drip to Targeted COIs we want to surface to
Pending · call analysis

COI Conversation Activation

In Conversation → Engaged · structured 30-min agenda + referral framing
Feeds Sellers · Stage 02 Engagement
Pending · call analysis

Engaged-COI Referral Cadence

Active referrers · monthly relationship cadence · cross-handoff with Wally
Standalone · cross-audience signal
Pending · call analysis

First-to-Know COI Activation

Tier 1 archetypes (insurance brokers, T&E attorneys, succession advisors) — the earliest-signal partnerships
Why these are placeholders Each COI play needs Discovery Questions, Messaging & Scripts, and Objection Handling grounded in real partner language — not invented by us. The 18 recorded calls Mike has plus the COI-specific conversations Wally is running this quarter supply that language. When analyzed, those calls populate each card here into the full 8-element format used for Cold Outbound.

The plays are the actions. Below: the campaigns and assets running right now to support the COI motion.

Section 8
What's running right now

Campaigns & assets in flight.

The executional layer for the COI play. Which campaigns are deployed, which assets exist, which need building. The COI one-pager (Partner With Us) is the headline collateral; the cadence cards govern the rhythm.

TIA Floor Sourcing

Where these categories came from.

The tier structure above didn't come from a desk. It came from the TIA Capital Ideas show floor on April 15. The exhibitor list is the COI universe: every booth was a service provider to T&L owners, which is the literal definition of a COI. The 5 tiers below were built by walking the floor, talking to vendors, and mapping who was there.

Why the exhibitor floor was the sourcing event.

TIA Capital Ideas exhibitors are factoring companies, insurance brokers, financial advisors, M&A attorneys, CPAs, TMS vendors, freight tech, and capital partners — every category of advisor who already has a trusted relationship with T&L owners. They're not prospects we're trying to convince to know the industry. They're already in it, talking to our ICP every day.

Walking the floor, vendor by vendor, gave us three things at once: a real category map (not theoretical), early relationships with named individuals at the booths, and a competitive read on how every other firm in the room positions itself.

The competitive read that sharpened our positioning.

The dominant message on the floor was defensive: protect against insurance risk, protect against legal risk, protect against fraud, protect cash flow. Sensible vendors selling sensible services. But almost nobody on the floor was talking about growth — about taking the business to peak value and exiting on the owner's terms.

That gap is Next Mile's positioning. Growth-oriented, operator-experienced, sell-side-only. The COI one-pager and the T&L Owner's Journey handout both lean into this contrast deliberately. When a COI hears our pitch after spending two days hearing risk-mitigation pitches, the difference registers immediately.

35 contacts captured on the floor.

Wally and Mike worked the floor with the COI one-pager in hand. By close of show, 35 named COI contacts had been captured (per Spoke Marketing Phase 2 Build scope · imported with the broader 53-contact post-TIA bundle of 12 sellers, 6 buyers, 35 COIs).

All 35 land in HubSpot tagged by category. The Phase 2 Build will tier them across Targeted / In Conversation / Engaged based on conversation depth at the booth. Most start at Targeted (targeted, no real conversation yet) or In Conversation (had a real conversation, mutual interest, no commitment).

Qualified leads from the pre-show campaign.

The pre-show email campaign also surfaced COI candidates before the show even started. Highest-priority follow-ups going into the floor:

  • Wendy MacLean · Lumenalta · meeting confirmed at TIA (replied to Email 4b, on the calendar pre-show)
  • Nick Antoine · Redarts Capital · replied to Email 2 (buyers list)
  • Michael Foster · Apex Capital · clicked Email 4b
  • Jennifer Recker · US1 Industries · clicked Email 4b
  • Patrick Garcia · LT International · clicked Email 2
  • Steve Blum · Tuya Tech · clicked Email 2

The Q2 qualification goal.

From the TIA campaign launch report: "qualify 3-5 COIs who can refer sellers in the $5M-$50M range within 90 days of the show." That's the operational target the floor sourcing rolls up to. 35 captured · 5 qualified · 1 referral closed inside the 90-day window is the funnel we're managing to.

Wally's top-5 Q2 goal (in the Growth Plan) is the same number, viewed from the other side: who are the five highest-leverage relationships from the 35, and what does it take to walk each one from Targeted to In Conversation and at least one of them to Engaged.

Owners: Dan + John.

Per the TIA segmentation owner map, Dan and John lead COI relationships. Wally is the senior sponsor for top-tier targets (the Engaged-bound relationships); Mike enters on specific deal-flow alignment conversations. The COI play stays under Dan + John as the systematic operating layer with Wally selectively engaged for the highest-value introductions.

See the Campaign Flow sub-tab for the Targeted / In Conversation / Engaged touch cadence by tier. See Appendix · COI One-Pager for the actual collateral Wally and Mike used on the floor.

TIA Floor Tactical Play

The 76 named contacts behind the 35.

Before TIA, the team mapped 20 priority COI companies with 76 named contacts confirmed on the attendee list, including 5 HubSpot-warm contacts already engaged from the pre-show campaign. The 35 captured COI relationships out of those 76 became the working pipeline; the rest are the next-tier targets to revisit through the COI cadence.

Priority Companies
20
Across the 5-tier framework
Named Contacts at TIA
76
Names + titles confirmed pre-show
HubSpot-Warm at TIA
5
Engaged email campaigns + on attendee list

Top 5 priority targets for the floor.

The "if we only had time for 5 conversations" list. Walk the floor with intention, not impressions.

  • Reliance Partners · Tier 1 Insurance · first to know when an owner is thinking exit · 6 named contacts including Graham Gonzales (EVP Sales), Jessie Merritt (EVP Sales), Mark Vickers (EVP Head of Intl Logistics)
  • Roanoke Insurance Group · Tier 1 Insurance · deep owner-level relationships · President Karen Rzeszutko + VP David Pasco on site (decision-makers who can formalize a partnership)
  • Triumph ★ WARM · Tier 1 Finance · Tom Gioia replied to Email 4b · 3 named TIA attendees including Kelly Gindlesperger (Sr. Manager Partner Development) and Matthew Silver (SVP Enterprise Partnerships)
  • McLeod Software · Tier 2 TMS · embedded in large-brokerage ops · 7 named contacts including Clint Hardy (VP Sales) and Nora Griffin (Marketing Dir Partner Alliances)
  • Truckstop.com · Tier 5 Data · CRO Paul Malone + Head of Innovation Jacky Zhao on site · broad reach across freight broker network

Caveat per Mike: "This list is AI-generated based on market data and exhibitor relevance. A better list starts with who we already know — leverage existing relationships first." Future floor plays should start with leadership-team connection mapping (who has a 1, 2, or 3-strength relationship at each company) before defaulting to AI-prioritized targets.

The 5 HubSpot-warm contacts at TIA.

These five engaged with the pre-show email campaign and were confirmed on the TIA attendee list. The opener: "We sent a campaign to TIA attendees a few weeks back and you opened/clicked — wanted to connect in person. We're Next Mile M&A..."

  • Wendy MacLean · Managing Director · Lumenalta · ★ replied + clicked Email 1 · meeting confirmed at TIA
  • Mark Evans · VP Business Development · Complete Shipping Solutions · ★ replied to Email 3b (Past TIA Attendees)
  • Nick Petrick · Director · Harris Williams · clicked Email 4b (Cold TIA Attendees)
  • Michael Foster · Sr. NextLOAD Product Manager · Apex Capital Corp · engaged across multiple campaigns
  • Jennifer Recker · General Manager · Keystone Lines (US1 Industries) · engaged across multiple campaigns

Triumph also had two warm contacts (Tom Gioia replied, Cody Rothwell clicked) who weren't on the attendee list but work at a confirmed exhibitor. Used as the opener when meeting Kelly, Jarad, and Matthew at the Triumph booth.

Vendors mapped to seller lifecycle stage.

The floor isn't all the same conversation. Different vendor categories see brokerage owners at different stages of the T&L Owner's Journey. The conversation angle adjusts accordingly.

  • Stage 1–2 (Launch / Growth · <$5M): Factoring · Load board
  • Stage 3 (Scale · $5–20M): TMS · Staffing · Insurance
  • Stage 4 (Optimize · $20–50M): TMS · Insurance · Analytics
  • Stage 5 (Ceiling / Exit Window · $50–100M): Insurance · TMS · M&A ← Next Mile
  • Stage 6 (Transaction · $100M+): M&A · Insurance
  • Stage 7 (Post-Close): M&A (integration support)

This stage-vendor map is the explicit version of the COI tier framework. It mirrors and operationalizes the seller-side lifecycle in the T&L Owner's Journey under Sellers.

Before / At / After the show.

Before: Pre-conference outreach to top 10 with a personal connection. Warm leadership-team intros convert at a much higher rate than cold booth stops.

At: Walk the floor with the priority list. Lead with the 30-second script. Get a post-show follow-up commitment, not a partnership closure.

After (within 48 hours): Personalized follow-up referencing the specific conversation. Propose a 20-minute structured COI partnership call. The deliverable is a formal referral relationship — not a one-off intro.

This Before/At/After cadence is the template for every future trade show, not just TIA. The cost of running it consistently is small; the compounding effect on the COI ecosystem is large.

The Hidden Tier · buyers and PE as validation engines.

The exhibitor list isn't the only COI pool at TIA. Strategic buyers and private equity contacts from the Buyers database who attend TIA become a parallel validation channel — they refer sellers that don't fit their own mandate but are still credible Next Mile engagements.

This is the inversion of the standard buyer relationship: instead of asking "what would you acquire," ask "what gets thrown back as too small, off-thesis, or wrong-geography for you?" Those rejected deals are perfect Next Mile referrals, and the buyer keeps the relationship credit for the introduction.

Six post-TIA buyer contacts were captured at the show. As the Buyers database migrates into HubSpot (see Obstacles & Opportunities · 05), this Hidden Tier validation play becomes structural rather than ad hoc.

Where the named relationships live.

Per the post-TIA bundle (53 contacts · 12 sellers · 6 buyers · 35 COIs), the Show Floor Game Plan identified 76 named individuals across 20 priority companies. Phase 2 HubSpot Sales Hub Build will land these against the right contact-type tagging:

  • COI contacts → tagged by tier + company. Owner: Dan + John.
  • Buyer contacts from the floor → tagged to the Buyers database when migrated. Owner: Mike + Wally.
  • Seller contacts from the floor → land in Engaged Early / Engaged Ready based on conversation depth. Owner: Mike + Wally.

The full 76-contact breakdown by company is in the Spoke Marketing Phase 2 Build SOW — too long to reproduce here. Ciara's HubSpot tagging makes it queryable rather than a static list.

Sequencing

The rhythm per tier.

Cadence escalates with engagement. Targeted is content-led drip; In Conversation adds personal touch quarterly; Engaged is full elevated relationship including real-time deal updates and recognition.

Targeted
Quarterly drip · content-led
4 touches per year · all content-led
  • Touch 1: Introduction with one customer story
  • Touch 2: Process explainer ("here's what happens when you refer us a seller")
  • Touch 3: Comparable / deal flow update ("here's what's been happening")
  • Touch 4: Soft ask · 15-minute intro call
In Conversation
Monthly content + quarterly personal
12 content touches · 4 personal · 1 dinner
  • Story or comparable each month
  • Quarterly personal call or note from Mike, Wally, or Dan
  • Annual COI dinner or event invitation
  • Goal: warm enough that the first referral happens
Engaged
Same monthly + elevated personal
Monthly content · real-time updates · recognition
  • Same monthly content rhythm as In Conversation
  • Real-time updates when their referrals progress
  • Co-branded content opportunities ("here's a piece you can send your clients")
  • Higher-priority access to Mike and Wally
  • Recognition: referral hall of fame, public thank-you when their referral closes
Calls to Action by Stage

What we ask a COI to do.

Each stage has one ask. Multiple asks per touch is the fastest way to make a busy professional ignore the next email.

Awareness · Targeted
Read this story. Save our number. Know what we do.
Interest · Targeted → In Conversation
15-minute intro call. Educational lunch.
Activation · In Conversation → Engaged
Send us your first referral. Co-host a client event.
Reinforcement · Engaged
Send us your next one. Feature your client win.
Referral Economics · Resolved Mar 16, 2026

How COIs get paid.

Designed to make COIs excited, not reluctant. Year-1 share is deliberately generous. Year-2 keeps relationships warm without creating perpetual obligations.

Year 1
20% of Next Mile fee

Paid on every successfully closed deal sourced through the COI's introduction.

Calculated on Next Mile's earned success fee at close.

Year 2
10% of Next Mile fee

For deals closed within the 6-month window after the qualifying introduction is recorded.

After 6 months, the introduction is considered closed; no further referral fee applies.

Portal Exception
Subscription Track

Portal-only relationships do not generate the standard COI fee.

If the relationship later converts to a full M&A engagement within the 6-month window, full COI economics apply.

Tracking Discipline

Nothing kills a COI relationship faster than not knowing what happened.

Every COI referral needs to be tagged in HubSpot with the referring COI so credit is unambiguous and follow-up communication closes the loop. This is on the gating-required list for the Sales module build.

  • At intro required: Source = COI · Referring COI = [name] · Date · Conversation context
  • At stage change required: Status update sent to the referring COI within 48 hours
  • At close required: Recognition note + fee payment + permission for case-study reference
  • If lost required: Direct call from Mike or Wally to the COI explaining why · keeps the channel intact
Channel Mix

Where we reach a COI.

COIs are professionals; they live on email and LinkedIn. In-person events (especially TIA) carry disproportionate weight. Phone is reserved for active relationships.

Channel Targeted In Conversation Engaged Use case
Email Primary across all tiers. Quarterly drip for Targeted, monthly for In Conversation/Engaged.
LinkedIn Highest-leverage channel for COIs. Sales Navigator targeting, content engagement, mutual-connection visibility.
Phone · In Conversation quarterly check-in, Engaged real-time deal updates.
Events / dinners TIA, regional events, hosted dinners. Annual COI-only dinner for In Conversation/Engaged.
Direct mail · · Engaged only. Annual industry report mailed to top COIs.
Co-branded content · · Engaged only. Pieces they can send their clients with their own branding alongside ours.
LinkedIn · The COI Channel

Where COIs already live.

M&A attorneys, CPAs, wealth managers, and CFOs are LinkedIn-native. They post, they engage, they read. The COI channel investment on LinkedIn is bigger than on the seller side because the audience uses it more.

How LinkedIn earns the COI.

Goal is to become a recognized name in their feed before any direct outreach. By the time we send a Targeted intro email, the COI should have seen Mike or Wally's name three times.

  • Sales Navigator targetingBuild saved searches by category (M&A attorneys, T&L CPAs, wealth managers in finance with T&L exposure). Rotate weekly InMails to highest-fit prospects.
  • Content for the COI's voicePosts framed for an attorney or CPA to comment on, share, or use in a client conversation. Educational, not promotional.
  • Mutual-connection visibilityMike and Wally engage with COI posts that touch on succession, M&A, or T&L. Visibility before pitch.
  • In Conversation engagement loopComment on every post by named In Conversation COIs. Light, frequent, genuine. Goal: stay in the field of view between drip touches.
  • Engaged co-postingWhen a Engaged COI sends a referral that closes (with permission), repost their reflection or co-post a case study tagged to them.
  • Hall of fame postsQuarterly named recognition for top referring COIs. Public thank-you. Reinforces the emotional reason they refer.
Programmatic for COIs

Audience-built display for category targeting.

Programmatic for COIs is narrower than for sellers. The audience is finite (T&L M&A attorneys, T&L CPAs, wealth managers in cities where T&L is dense). High-fit audience builds matter more than reach.

Where programmatic moves the needle.

Use programmatic to make a Targeted audience build feel like recognition. Once a COI is at In Conversation or Engaged, organic engagement and direct relationship carry more weight than paid placement.

  • Category-built audiencesLinkedIn matched audiences by job title (M&A counsel, CPA, fractional CFO) plus industry filter (transportation, logistics, freight).
  • Comparable-led creative"What just sold in T&L" creative outperforms generic firm branding. Comparables travel naturally.
  • Geo-targetingHeavy COI density geographies first: Chicago, Atlanta, Dallas, KC, Memphis. Light national overlay.
  • Retargeting on COI-specific contentAnyone who hits the "How the 20% works" page or the "What a good referral looks like" page gets light retargeting.
  • No display retargeting on EngagedOnce a COI is engaged, paid display is wasted spend. Direct relationship beats programmatic.
  • Budget gateCOI programmatic is funded only after Sellers programmatic is producing measurable warm-account engagement.
Content Needs · COI Angle

Library titles framed for the referrer.

The same Exit Readiness Library carries this play. The frame shifts: "make them look smart in front of their client." Real Client Stories travel especially well with COIs. Deal Structure & Terms is high-relevance for attorneys, CPAs, wealth managers. CTA stays consistent: "Schedule a Confidential Conversation."

Real Client Stories · COI framing
All 6 alumni titles, but emails reframe the takeaway for client outcomes vs. internal Next Mile language. Dan K's compressed timeline plays to CPAs/attorneys. Doug's 4-year journey works for wealth managers. Roger & Deanie's earnout reality works for any COI advising on deal structure.
Source: 6 alumni interviews · same library
Deal Structure & Terms category
"Understanding Earnouts" · "Seller-Side vs. Buyer-Side Representation" · "What's in an LOI?" · "How to Evaluate Multiple Offers" · "Purchase Agreement Terms" · "Transition Requirements." High-relevance for attorneys, CPAs, wealth managers. Forwardable verbatim.
Source: John · Exit Readiness Library
Process explainers
"The Role of an M&A Advisor: What They Actually Do" demystifies our role for the COI's client conversation. "From First Call to Close: The M&A Timeline" sets realistic expectations. Both forwardable.
Source: John · Exit Readiness Library
"How the 20% works" explainer
Next Mile-specific (not in John's library). Clear dollar examples. What the COI gets paid on a $40M deal. When the fee is paid. How attribution is tracked.
Status: TBD · Next Mile-original asset
Quarterly market reports
Built from "What just sold" comparables + Industry-Specific Insights from the library. T&L deal flow, multiples, trends. Co-brandable for Engaged COIs to forward under joint framing.
Status: cadence to define · cross-play asset
Co-brandable library access (Engaged)
Permission-granted access for Engaged COIs to add their logo to Industry-Specific Insights and Deal Structure pieces. Reinforces the "look smart" loop. Real Client Stories stay Next Mile-branded; COI gets credit when their referral becomes a story.
Status: Engaged-only · post-first-referral

Standard CTA: Every COI-facing email ends with the same "Schedule a Confidential Conversation" CTA pointing to the seller's free consultation. The COI's value to their client is making the introduction; the consultation is the proof point that we deliver value beyond the introduction.

Campaign Flow · COIs

Library titles framed for the referrer.

"Make them look smart in front of their client" is the test every touch passes. Same library content as Sellers, reframed for COI forwarding. Real Client Stories travel especially well with attorneys, CPAs, wealth managers, fractional CFOs. CTA stays consistent.

Targeted

Targeted

GOAL: First substantive conversation. Move to In Conversation.

SOURCE: TIA attendees · category research · profile match · LinkedIn

Q1
Email · quarterly
Intro + story
"How Dan Krivickas Compressed His Timeline by 4+ Months" + Next Mile intro
CTA: Schedule a Confidential Conversation
Q2
Email · quarterly
Process explainer
"The Role of an M&A Advisor: What They Actually Do" + COI fee model
Q3
Email · quarterly
Comparable / deal flow
"Recently closed in T&L" digest · forwardable to clients
Q4
Email · ASK
Soft ask
15-min intro call · educational lunch · "your clients in T&L?"
CTA: Schedule a Confidential Conversation
Running in parallel · digital layer
Sales Navigator targetingBy category · M&A attorneys, T&L CPAs, wealth managers, fractional CFOs.
Mutual-connection visibilityMike/Wally engage on COI posts before any pitch · visibility before ask.
Programmatic · category audienceComparable creative outperforms brand creative · geo-targeted on T&L-dense markets.
Exit triggers
→ In Conversation15-min call booked
→ In Conversation (manual)Strong content engagement · manual escalation
→ ArchiveNo engagement after 8 quarters
Library titles for COI cold drip
  • Story rotation: Lead with Real Client Stories. Dan K's compressed timeline plays well to CPAs/attorneys. Doug's 4-year journey works for wealth managers. Roger & Deanie's earnout reality works for any COI advising on deal structure.
  • Process explainers (COI angle): "The Role of an M&A Advisor: What They Actually Do" + "From First Call to Close: The M&A Timeline" gives realistic expectations to set with clients.
  • Differentiator: "Seller-Side vs. Buyer-Side Representation: What's the Difference?" makes it easy for a COI to explain why they referred to Next Mile vs. another firm.
In Conversation

Identified Plus Conversation

GOAL: First referral. Move to Engaged.

SOURCE: Targeted graduates · TIA conversations · referrals from Engaged

M1
Email · monthly
Story
"Wally's Path: From Founder to Managing Partner"
M2
Email · monthly
Comparable
Recently closed deal sheet · forwardable proof
M3 · QUARTERLY
Phone
Personal check-in
Mike, Wally, or Dan · just hello · tailored insight
M4
Email · monthly
Story
"Carol's Story: Finding Marketability Where She Thought There Was None"
M5
Email · monthly
Process insight
"Common M&A Pitfalls for First-Time Sellers" · forwardable
ANNUAL
Event
COI dinner
In Conversation + Engaged invited together · cross-pollination
Running in parallel · LinkedIn engagement loop
Comment on every named In Conversation postMike + Wally · light · frequent · genuine.
Manual InMail outreachWhen a story or comparable lands well · personal note from a principal.
Forwardable contentMake it easy to share with their client · co-brandable for highest In Conversation.
Exit triggers
→ EngagedFIRST REFERRAL SENT
→ TargetedCold 12+ months · reset to drip
Library titles in rotation for In Conversation
  • Real Client Stories: All 6 alumni rotate monthly. Same content as Sellers play but framed for client outcomes (less internal Next Mile language, more "what the seller got").
  • Forwardable insights: "Common M&A Pitfalls" · "What Makes a Transportation Business Marketable?" · "Why Customer Concentration Matters to Buyers" — pieces a COI can send their client verbatim.
  • Deal Structure category: "Understanding Earnouts" · "How to Evaluate Multiple Offers" · "Purchase Agreement Terms" — high relevance for advising attorneys and wealth managers.
  • Quarterly forwardable: Quarterly market reports the COI can send under their own framing. Co-brandable for top In Conversation contacts.
Engaged

Engaged

GOAL: Multiple referrals per year. Hall-of-fame relationship.

SOURCE: In Conversation graduates (first referral sent)

CONTINUING
Email · monthly
Same as In Conversation + co-branded
All 5 library categories · permission-granted assets they put their name on
REAL-TIME
Email / call
Status updates
Within 48 hours of any stage change on their referral
QUARTERLY
LinkedIn
Hall of fame
Named recognition post · public thank-you when their referral closes
ANNUAL
Direct mail + gift
Industry report
Printed annual report · Engaged only · plus annual gift (TBD protocol)
CONTINUING
Direct line
Elevated access
Mike + Wally direct · co-host client events · priority on new mandates
Recognition + relationship · no paid display
Public recognitionHall of fame LinkedIn posts (with permission) · case-study tags.
Co-brandable assetsLibrary pieces with permission to add their logo · sent to their clients under joint framing.
No display retargetingDirect relationship beats programmatic at Engaged. Spend goes elsewhere.
Exit triggers
→ Elite (TBD)Multiple referrals/yr · even higher access
→ Engaged continuingDefault · most stay Engaged indefinitely
→ In Conversation18+ months no new referrals · reactivate
Library titles available for Engaged co-branding
  • Co-brandable categories: Industry-Specific Insights and Deal Structure & Terms travel best with COI co-branding (less Next Mile-specific framing). Real Client Stories stay Next Mile-branded but the COI gets credit when their referral becomes a story.
  • Quarterly forwardable: Annual industry report (printed, mailed) is the headline Engaged asset.
  • Exclusive previews: Engaged COIs see new library content before public publish · gives them first-mover advantage with their clients.

Last: how we know the COI play is working. The leading indicators that tell us a referral is on its way before it shows up in pipeline.

Section 9
What it costs, how we measure

Budget & KPIs.

The economics of the COI play — referral economics already set (20% Y1 / 10% Y2), and the leading indicators that signal referral momentum before pipeline impact.

Measurement framework

Leading indicators first.

Pipeline impact from COIs is a lagging metric — by the time a COI referral closes a deal, the COI relationship has been live for months. The leading indicators tell us whether the engine is healthy before the lagging numbers do.

  • COIs in ConversationNumber of COIs we've had at least one structured 30-min conversation with. Health: growing each quarter.
  • Engaged COIsCOIs who have either referred or signaled intent to refer. Health: at least 5 by EOY 2026 per Wally's Q2 goal.
  • Referrals receivedActual seller introductions sourced from COIs. Health: at least 3 per quarter once the engine is mature.
  • Referral → deal conversionOf referred sellers, how many advance to Stage 04 Evaluation. Health: meaningfully higher than cold outbound — that's the point of the play.
  • Referral economics20% Year 1 / 10% Year 2 of net success fee. Locked in March; not negotiable per relationship.
Targets pending Specific quarterly targets for each indicator are pending baseline data from the first two quarters of active COI work (Q2 and Q3 2026). Until then, the framework is in place and the directional health language above describes how we read the early signals.
Buyers · Build · Next 60 days

Buyers.

Strategic & financial T&L acquirers · 300+ database
3
Audience tiers
Known Database · Met at TIA · Engaged on Current Deal
300+
Strategic & financial
buyer database
2x
Content reuse
same content closes Sellers
The Single Most Important Message

"Buyers are not the customer. They are the market we deliver to."

The buyer play has two outcomes. One: when we bring a deal to market, the right buyer raises a hand quickly. Two: the deal-flow content we send to buyers doubles as comparables for sellers and COIs. This is the highest-leverage content investment in the engine. Build once, distribute everywhere.

Audience · Strategic & Financial Buyers

Buyers · the demand side.

Buyers don't close deals directly. They generate demand and comparables that energize Sellers and COIs. Three tiers (Known Database · Met at TIA · Engaged on Current Deal), 300+ relationships in Mike's system, scoped for Phase 3 activation. This is the leanest of the three audience plays today — the foundation is real, the build-out is sequenced after Sellers and COIs mature.

Section 1
Who they are

300+ buyers, three tiers.

The Buyer audience is Mike's decades-of-operating asset: relationships with strategic acquirers (PE firms, family offices, strategic-investor corp dev) and financial buyers across the T&L vertical. The database lives in Mike's homegrown system and is being migrated to HubSpot in Phase 3.

Two Outcomes

What buyers give us.

Buyers don't pay us. The seller does. But cultivating the buyer side produces two outcomes that make the seller play work.

Outcome 1 · Demand.

When we bring a deal to market, the right buyers raise their hand fast. Speed of buyer response shortens diligence, increases tension across competing buyers, and gives the seller more leverage on price and terms.

A 300+ database with tagged preferences (mode, size, geography) is the dial-up. The cadence keeps buyers warm so we don't have to call cold when we have something to sell.

Outcome 2 · Comparables.

The deal flow content we send to buyers doubles as comparable evidence for sellers and COIs. "Coming to market" previews and "recently closed" deal sheets are the same artifacts that energize the other plays.

Build once, distribute everywhere. Highest content ROI in the engine.

Status

Where the play stands today.

Build sequencing recommendation: Buyers comes after Sellers and COIs. Can largely run on quarterly comparables and deal flow rhythm once content engine is live.

01
Database Established300+ strategic & financial T&L buyers
✓ Established
02
Database Health AuditCurrency check, tagging by mode/size/geo, refresh project
Open · gating
03
Known Database CadenceMonthly market color, "coming to market," "recently closed"
Define
04
Met at TIA OnboardingTIA-met buyers · profile capture · "great to meet you" sequence
Drafted
05
Buyer Profile Capture FormWhat are they looking for · size · mode · geo
TBD
06
"Coming to Market" MechanismHow we tease confidentially · NDA gate
Concept
07
Buyer Roundtables / WebinarsQuarterly virtual format
TBD
08
Content Production CadenceMonthly market color · monthly deal sheets · sector trends
Define
Database Health · Open Decision

Is the 300+ database current and tagged?

Open question flagged in the playbook input: is the buyer database current and properly tagged, or does it need a refresh project before the cadence kicks off? Worth confirming with Mike before any scaled outreach to Known Database.

○ Define
Buyer Database Health Audit
Confirm database currency: how recently were contacts validated? Are profile preferences (mode, size, geo) tagged? Is contact attribution (champion vs. firm) clean? If audit reveals significant decay, recommend a one-time refresh project (similar to ZoomInfo validation) before scaled cadence begins.
Owner: Mike + Ciara · Trigger: before Known Database cadence launch
What's Inside

The Buyers play in operational order.

Buyers is the leanest of the three sales plays. Foundational structure is in place; messaging, conversation, and network detail are on the editorial roadmap.

01
OverviewTwo outcomes, status, database health (300+ buyer decision pending)
✓ Complete
02
Triggers & AudienceThree buyer tiers
Partial · tier structure present, deeper personas pending
03
Messages & NarrativeBuyer-side narrative, opening hooks for the strategic / financial distinction
Awaiting · editorial roadmap
04
ConversationIntro Zoom arc, mandate alignment, cultural-fit filter, IOI request
✓ Complete
05
Network & COIsWhere strategic and financial buyers source (PE conferences, syndication networks, banker networks)
Awaiting · editorial roadmap
06
Campaigns & AssetsSequencing, CTAs by stage, channel mix, LinkedIn for buyers, programmatic, content needs (buyer angle), dual-purpose multiplier, campaign flow
✓ Complete
07
Budget & VOCBuyer-side voice of customer, budget allocation for Buyers
Awaiting · no VOC or Budget content yet

Who they are is clear. What they say about Next Mile — and what they want from a seller relationship — is below.

Section 2
What we heard them say

Voice of the buyer.

Verbatim from buyer-side voices about what makes a seller engagement worth pursuing — and what kills it before LOI. Less mature than Seller VOC; the buyer-side voice will deepen as Phase 3 activates.

Awaiting · Editorial roadmap

Budget & VOC is on the way.

Voice of the Customer from the buyer side (what buyers say about the Next Mile process, deal quality, fit alignment), plus the budget allocation for Buyers specifically. Currently no VOC interviews from the buyer side have been logged; Budget hasn't been split by play. Both are on the editorial roadmap.

Now: where buyers are in their own journey when a deal becomes interesting to them.

Section 3
Where they are in their journey

Buyer-side cadence.

Buyers don't have a single linear journey the way Sellers do — they have always-on acquisition mandates and discrete deal evaluation moments. Our cadence has to match: monthly market color when nothing is in motion; deal-specific intensity when a fit emerges.

Three Tiers

Where every buyer lands.

Buyer tiers track database membership and active engagement, not deal-readiness. Tier matters less than match: a Known Database buyer who matches an active deal jumps to Engaged on Current Deal immediately.

Known Database
Database
Known Database

Next Mile's database of 300+ strategic and financial T&L buyers, built over years. Tagged by mode preference (asset, asset-lite, warehousing), size band, and geography. Health audit recommended before scaled cadence kicks off.

GOAL: Stay current on T&L deal flow. Be ready when something fits.
Met at TIA
TIA-met
Met at TIA

Buyers we engaged with at the show but who weren't already in the database. New names, fresh signal. Onboard, capture profile, then merge into Known Database monthly rhythm.

GOAL: Profile capture. Add to Known Database.
Engaged on Current Deal
Engaged · live deal
Engaged on Current Deal

Buyers who have responded to outreach on a specific deal, attended a meeting, or expressed interest in a current opportunity. Move to the head of the line on new opportunities. No automation: Mike, Wally, or assigned principal handles directly.

GOAL: Sign NDA. Review CIM. Submit IOI.

Their cadence shapes how we speak to them. The narrative is below.

Section 4
What we say to them

Comparables, not pitches.

Buyers don't need to be sold on Next Mile. They need a steady stream of qualified deal flow and the comparables that help them sharpen their own mandates. The narrative is about being a reliable source of intelligence and selective opportunity.

Awaiting · Editorial roadmap

Messages & Narrative is on the way.

The buyer-side narrative. How Next Mile positions itself to strategic acquirers (operator track record, T&L specialization) vs. financial buyers (deal economics, exit alignment). Opening hooks for each tier. Today this lives in Mike's and Wally's instinct on a per-buyer basis; pulling it forward into a named place is on the editorial roadmap.

The narrative is informational. The conversation is transactional. Below: how it plays out.

Section 5
How the conversation goes

Deal-led, not relationship-led.

Buyer conversations are episodic — they happen when a specific deal triggers them. The structure is: confirm fit against the buyer's mandate in 5 minutes, then provide the artifact (teaser, CIM, financial summary) that lets them decide on next steps.

How the Buyer Conversation Goes

A fit filter, not a courtship.

Mike runs buyer conversations to qualify whether they belong in the database, not to convince them to join it. The questions surface mandate alignment, past-deal patterns, and the cultural-fit filter that protects sellers from buyers who rip companies apart. The new-buyer questionnaire (from Mike's system) feeds the structured filter side.

01
Intro Zoom · 15-min strategic fit · Stage 06 Market Engagement

The first real buyer conversation. Mike runs it. The hook: "Tell me about the last 2 or 3 deals you've done. What worked, what didn't." Past-deal pattern matching reveals more than any questionnaire about who they really are.

02
Mandate alignment · Stage 06

What sizes, what modes, what geographies, what structures. Mike's system captures this as filters on the buyer record. Specific exclusions matter: "California" came up on the Feb 18 system walk-through as a hard-no for one buyer. Those exclusions get recorded.

03
Cultural-fit filter · the protection layer

Mike on the Feb 18 walkthrough: "We want to make certain that they are the type of buyer we're interested in, not just a pure financial buyer. They're not into ripping companies apart, blowing employees up, that kind of stuff." This is the filter. It's subjective, it's slow, and it's what makes the database trustworthy.

04
New Buyer Questionnaire · structured intake

Mike's buyer questionnaire formalizes the filter inputs. Captures the explicit criteria; the cultural-fit filter still lives in the conversation, not the form. Together: structured data + operator judgment.

Where buyers actually gather is below.

Section 6
Where they hang out

Industry conferences · deal-flow newsletters.

Buyers are professional acquirers. They attend industry M&A conferences, subscribe to deal-flow newsletters, and rely on a small set of trusted advisor relationships for proprietary deal flow. Earning a place in that small set is the long game.

Awaiting · Editorial roadmap

Network & COIs is on the way.

Where strategic and financial buyers source their deal flow: PE industry conferences, T&L specialist banker networks, syndication channels, LP introductions. Today this content sits inside Mike's relationships and Kevin Nadeau / 10 Street-style named conversations. Pulling it forward into a named place is on the editorial roadmap.

See: COIs → for the COI engine that feeds Sellers (and could feed Buyers).

The named motions we'll run to reach buyers are below.

Section 7
The plays we run

Named Buyer motions · awaiting Phase 3 activation.

Below are the named motions the Buyer play will run, organized by what they feed. Buyer play activation is sequenced for Phase 3 (Fall 2026); the plays below are scoped today but content build-out follows database migration and the call analysis loop. Each card expands into the same 8-element format as Cold Outbound when ready.

Standalone · Buyer database engagement
Pending · Phase 3

Known Database · Monthly Color

300+ database · monthly market color & deal-flow update
Pending · Phase 3

Met at TIA · Onboarding

New buyer contacts captured at TIA · 3-touch onboarding into Known Database cadence
Feeds Sellers · Stage 06 Market Engagement & Stage 07 Connected
Pending · Phase 3

Engaged-on-Current-Deal

Deal-specific buyer outreach when a seller is in Market Engagement · NDA, teaser, CIM
Cross-feeds COIs
Pending · Phase 3

Buyer-side Referral Capture

Buyers who decline a deal but refer to a peer · feeds back into the seller pipeline as warm signal
Why these are placeholders · why Phase 3 Buyer play activation depends on (a) database migration into HubSpot (300+ contacts from Mike's system into properly-segmented HubSpot records), (b) the call-analysis loop from Sellers and COIs producing the buyer-side voice we use, and (c) Sellers and COIs reaching enough operational maturity that Buyer outreach has artifacts to send. Today the foundation is real (database exists, tiers defined, cadence framework in place); the named motions activate in Phase 3.

The plays are scoped. Below: what's currently running on the buyer side — sparse today, by design.

Section 8
What's running right now

Campaigns & assets today.

The buyer-side executional layer today is intentionally minimal — Phase 3 activation hasn't begun. What exists is the foundation (database, tier framework, cadence cards). What's running is light: the post-TIA new-buyer capture and Mike's ongoing deal-specific outreach for active sellers.

Sequencing

The rhythm per tier.

Buyers want signal, not nurture. The cadence is dense with substance: market color, deal flow, sector insight. Generic content ages out fast in this audience.

Known Database
Monthly market color & deal flow
12 substantive touches per year
  • "Coming to market" preview (high-level teaser)
  • "Recently closed" comparable (anonymized where required)
  • Sector trend or insight (LTL, brokerage, warehousing, drayage, last-mile)
  • Quarterly buyer roundtable invitation (virtual)
Met at TIA
Onboarding · then merge into Known Database
3 onboarding touches · then Known Database monthly
  • Touch 1: "Great to meet you at TIA" personal note
  • Touch 2: Profile capture (size, mode, geography)
  • Touch 3: First market update
  • Then: merge into Known Database monthly rhythm
Engaged on Current Deal
Active deal-specific · no automation
As frequent as the deal demands
  • Mike, Wally, or assigned principal handles directly
  • NDA execution · CIM review · IOI submission
  • Q&A coordination, management presentation scheduling
  • No marketing-automated content during active engagement
Calls to Action by Stage

What we ask a buyer to do.

Awareness · Known Database
Stay current on T&L deal flow.
Profile capture · Met at TIA
Tell us what you're looking for so we can match.
Active engagement · Engaged on Current Deal
Sign NDA. Review CIM. Submit IOI.
Channel Mix

Where we reach a buyer.

Email is primary. LinkedIn for awareness. Phone for active deals. Virtual roundtables and TIA-class in-person events for relationship density.

Channel Known Database Met at TIA Engaged on Current Deal Use case
Email Primary across all tiers. Monthly market color for Known Database; onboarding sequence for Met at TIA; deal-specific for Engaged on Current Deal.
1:1 phone · Engaged on Current Deal deal-specific. Mike or assigned principal direct.
LinkedIn · Awareness. Buyer firms post their own deal activity; engagement keeps us in their feed.
Quarterly buyer roundtables · Virtual format. Sector insight + comparables. Sponsor-style without being a webinar.
TIA & industry events In-person relationship density. Met at TIA emerges from these. Engaged on Current Deal gets dinner if a live deal is in the room.
LinkedIn for Buyers

A different posture than for sellers.

Buyer firms post their own deal activity, sector commentary, and team announcements. The play here is engagement and visibility, not direct outreach. Mike and Wally are visible to buyers as a credible counterpart, not as a vendor pitching them.

Buyer-facing LinkedIn moves.

Goal is firm-level recognition: when our deal lands in their inbox, they recognize the names. Lighter content frequency than seller side; higher quality threshold.

  • Firm-page post engagementComment on buyer firm announcements, sector posts, and acquisition news. Light, professional, not promotional.
  • Sector commentaryMike or Wally posts on T&L sector trends as an operator. Buyers see thoughtful industry voice, not a sales pitch.
  • "Coming to market" teasers (anonymized)Carefully framed teasers about new mandates without violating confidentiality. Drives buyer-side inbound.
  • Sales Navigator for Met at TIA onboardingFind LinkedIn profiles of TIA-met buyers; connect post-event with a personalized note referencing the conversation.
  • Buyer firm trackingSaved searches monitor when known buyer firms post acquisition activity (positive signal for outreach about future mandates).
  • No direct askNothing from Mike or Wally on LinkedIn ever asks a buyer for a meeting. The ask happens via email or phone, never on LinkedIn.
Programmatic for Buyers

Deal flow visibility, not brand reach.

Programmatic on the buyer side is purely about deal-flow visibility. The audience is finite and known (the 300+ database, plus profile-match expansion). Spend goes to keeping Next Mile's deal flow content in the field of view of named buyer firms.

How programmatic earns its place on the buyer side.

Use programmatic for surround-sound on buyer firms during active deal cycles, and to keep "what just sold" content surfacing for warm Known Database buyers between monthly emails.

  • Buyer firm IP-targetingIP-targeted display on the office locations of named buyer firms. Lightweight reach; high recognition value.
  • "Coming to market" amplificationBoost organic teaser posts to LinkedIn matched audiences of M&A leadership at buyer firms.
  • Engaged on Current Deal surround soundDuring active Engaged on Current Deal deal cycles, IP-targeted display on the buyer firm reinforces our presence between principal calls.
  • Recently closed comparablesProgrammatic distribution of "recently closed" comparable content to the 300+ database. Same content reaches Sellers and COIs: the dual-purpose play.
  • Sector-specific creativeDifferent creative for asset, asset-lite, warehousing, last-mile audiences. The buyer firm pursuing brokerage doesn't want to see warehousing content.
  • No retargeting on cold buyersBuyer firms not in the 300+ database don't get paid retargeting. Spend is gated to known and warming audiences only.
Content Needs · Buyer Angle

Industry-Specific Insights carries this play.

John's Industry-Specific Insights category is built for the buyer audience. Six titles cover capacity, customer concentration, asset vs. asset-lite, carrier networks, freight market conditions, insurance/nuclear verdicts. Same library content also goes to Sellers (Engaged Early/Engaged Not Ready) and COIs (In Conversation/Engaged). Build once, distribute everywhere.

Industry-Specific Insights · 6 titles
"How Capacity Fluctuations Impact Transportation Valuations" · "Why Customer Concentration Matters to Buyers" · "Asset-Based vs. Non-Asset: What Buyers Really Care About" · "The Hidden Value in Your Carrier Network" · "How Current Freight Market Conditions Affect Exit Timing" · "Insurance Costs and Nuclear Verdicts: What It Means for Your Valuation"
Source: John · Exit Readiness Library
"Recently closed" deal sheets
Anonymized where required. Buyer type, rationale, multiple, structure. Not in John's library; built per deal. Same artifact buyers want is what sellers and COIs want.
Recurring · monthly · cross-play
"Coming to market" previews
Teasers (high-level, NDA-gated for full detail). Not library content; per-mandate. Drives buyer-side inbound; signals deal momentum to sellers and COIs.
Per-deal cadence
Quarterly buyer roundtable
Virtual 30–45 min event. Pulls one Industry-Specific Insight title from the library + 2–3 recent comparables. Sponsor-style without being a webinar pitch.
Quarterly · principal-led
Buyer profile capture form
Met at TIA onboarding tool. What are they looking for: mode, size, geography, structural preferences. Feeds the 300+ database. Not content per se; operational artifact.
Build once · always-on
The Dual-Purpose Multiplier

Same content. Three audiences.

The "what just sold" and "coming to market" content is the same artifact distributed to all three plays. This is why the buyer play earns its place in the build sequence even though it doesn't close deals directly.

Asset Known Database–Engaged on Current Deal Buyers Cold Targeted–Engaged Not Ready Sellers Targeted–Engaged COIs
"Recently closed" deal sheet Deal flow signal Comparables · "this is what's possible" Forwardable proof to clients
"Coming to market" preview Inbound capture Validation · the firm has motion Conversation starter with clients
Sector trend piece Strategic context Macro framing for owner conversations Educational forward to clients
Monthly market color Currency "Where we are" reference Recurring touchpoint with proof

Production cadence implication: the playbook input estimates 60–75 content units per year across all four plays, with a substantial portion sourced from the dual-purpose content built here. If production capacity can't hit that, the plays should be re-tiered to fit available bandwidth.

Campaign Flow · Buyers

Industry-Specific Insights carries this play.

Buyers want signal, not nurture. John's Industry-Specific Insights category is built for this audience. Same library content also goes to Sellers (Engaged Early/Engaged Not Ready) and COIs (In Conversation/Engaged). Build once, distribute everywhere. "Coming to market" content is per-mandate, not library.

Known Database

Known Database

GOAL: Stay current. Be ready when something fits.

SOURCE: 300+ database (health audit gating · open question)

M1
Email · monthly
Coming to market
High-level teaser preview · NDA-gated detail
M2
Email · monthly
Recently closed
Anonymized deal sheet · multiples + structure
M3
Email · monthly
Sector trend
"Asset-Based vs. Non-Asset: What Buyers Really Care About"
QUARTERLY
Event
Buyer roundtable
Virtual · 30-45 min · sector + comparables
M5
Email · monthly
Capacity insight
"How Capacity Fluctuations Impact Transportation Valuations"
M6
Email · monthly
Market color
"How Current Freight Market Conditions Affect Exit Timing"
Running in parallel · programmatic layer
Buyer firm IP-targetingNamed buyer firm office locations · high recognition value.
"Coming to market" amplificationLinkedIn matched audiences of M&A leadership at buyer firms.
Sector-specific creativeAsset / asset-lite / warehousing / last-mile creative split.
Exit triggers
→ Engaged on Current DealActive deal match
→ ArchiveDecay flagged in health audit
Library titles for buyer-side cadence
  • Industry-Specific Insights (primary): "How Capacity Fluctuations Impact Transportation Valuations" · "Asset-Based vs. Non-Asset: What Buyers Really Care About" · "The Hidden Value in Your Carrier Network" · "How Current Freight Market Conditions Affect Exit Timing"
  • Coming-to-market mechanism: Anonymized teasers (no library content) · NDA-gated for full detail. The library doesn't carry deal-flow content; that's bespoke per mandate.
  • Comparables (recurring): Same artifacts that flow to Sellers and COIs · deal sheets, multiples, structure.
  • Quarterly roundtables: Pull a sector trend from the library + 2-3 recent comparables · 30-45 min virtual.
Met at TIA

Met at TIA

GOAL: Profile capture. Add to Known Database.

SOURCE: TIA show floor · industry events · referrals

WK 1
Email · Touch 1
"Great to meet you"
Personal note · refs the conversation, not the pitch
WK 2–3
Email + form
Profile capture
Size · mode · geography · structural prefs
CTA: Complete profile
WK 4
Email · Touch 3
First market update
Sized to their captured profile · sector trend + comparable
MERGE
→ Known Database monthly
Now in Known Database rhythm
Profile-tagged · sector-targeted · added to 300+ database
Running in parallel
Sales Navigator post-event connectConnection note refs the conversation · Mike or Wally directly.
HubSpot record creationProfile capture → Known Database tagging → buyer database integration.
Cross-tagged Cold Targeted/Engaged EarlyIf they're also a potential seller (rare but possible at TIA).
Exit triggers
→ Known DatabaseProfile captured · move into monthly rhythm
→ Engaged on Current DealActive deal interest at the event itself
→ ArchiveNo response after 3 touches
Engaged on Current Deal

Engaged on Current Deal

GOAL: Sign NDA. Review CIM. Submit IOI.

SOURCE: Known Database active match · Met at TIA live deal · inbound on coming-to-market

STAGE 1
NDA
Confidentiality
Mike or principal issues NDA · quick turnaround
STAGE 2
CIM
CIM review
7-14 day review · centralized Q&A coordination
STAGE 3
Mgmt
Mgmt presentation
Prep dinner night before · role-play questions
STAGE 4
IOI
Indication of interest
Price + structure · compared against other IOIs
STAGE 5
LOI
LOI & diligence
"Abnormal ask" guard · data room access
STAGE 6
Close
Closing
Handoff to integration
Programmatic surround during active deal
IP-targeted display on buyer firmReinforces our presence between principal calls.
LinkedIn matched on deal teamReinforces "credible counterpart" framing.
No content marketing during Engaged on Current DealJust deal-specific comms · nurture pauses.
Exit triggers
→ Known Database celebrationDeal closes (won)
→ Known DatabaseDeal lost (didn't choose them)
→ Known Database or removeWalked away from the process

The measurement framework for buyers — the leading indicators that tell us the engine is healthy.

Section 9
What it costs, how we measure

Budget & KPIs.

The buyer play doesn't close deals directly — it generates demand and comparables. The measurement reflects that: throughput of buyer-side engagement, quality of comparables surfaced, conversion of buyer interest into seller-side deal activity.

Measurement framework

Demand generation, not deal closure.

Buyers measured by what they produce upstream — comparables, demand signals, buyer-side validation that makes Seller positioning sharper.

  • Database depthNumber of buyers in HubSpot, segmented by mandate (strategic vs. financial), size band, geography, and mode preference. Target: 300+ migrated and segmented by end of Phase 3.
  • Active buyer mandatesBuyers we know are actively looking right now, with mandate criteria documented. Health: at least 30 active mandates feeding any given Seller deal.
  • Monthly engagementOpen / click / reply rates on the monthly market color email. Target: 25%+ open, 5%+ reply.
  • Deal-specific response rateWhen we surface a Seller deal to matched buyers, how many engage? Health: at least 5 qualified buyer engagements per deal in Market Engagement.
  • Comparables producedRecent deal data (anonymized) we can share with Sellers in Stage 04 Evaluation. Target: 1 fresh comparable per Seller deal closed.
Targets pending Phase 3 Specific targets are pending Phase 3 activation (Fall 2026). The framework above is the structure we'll measure against once Mike's database is in HubSpot and the buyer-side campaigns are deployed.
The Record

The decisions log.

Detailed write-ups for resolved decisions and active programs. As Obstacles & Opportunities resolve in The Meeting tab, their full context lands here as institutional memory: the math, the rationale, and the criteria for revisiting. Anyone joining the team should be able to read this section and understand why we made every consequential call.

The institutional memory.

Twenty cards across five sections. A holds the decisions log. B holds the brand assets in production. C holds the call-by-call source material from the analysis loop. D holds the side-by-side matrices. E preserves content that lived in earlier versions of the playbook but was deliberately cut. Each card is referenced by name from somewhere else in the playbook; this is where the full context lives.

A

Decisions Log

Resolved Obstacles & Opportunities that became firm decisions, plus active programs in flight that will land here when they reach decision state. Each card carries the math, the rationale, and the criteria for revisiting.

Appendix A · Resolved Mar 16, 2026
✓ Solved

COI Referral Fee Structure.

The economics that make COIs excited about referring, not reluctant. Resolved on the Mar 16, 2026 design call between Mike, Wally, John, and Dan. Year-1 share is deliberately generous; Year-2 keeps relationships warm without creating perpetual obligations.

Year 1

20% of Next Mile success fee.

Paid on every successfully closed deal that originated from the COI's qualifying introduction. Calculated on Next Mile's earned success fee at close, not on enterprise value or other gross proxies.

Year 2 · 6-month window

10% of Next Mile success fee.

Applies only to deals that close within 6 months of the qualifying introduction being recorded. After 6 months, the introduction is considered closed and no further referral fee applies.

Portal Exception

Subscription track.

If the seller engages on the subscription/portal track (Track B) rather than the M&A track (Track A), referral economics adjust. Portal-only relationships do not generate the standard COI fee. If the relationship later converts to a full M&A engagement within the 6-month window, full COI economics apply on the M&A success fee at close.

Qualification Rules

What counts as a referral.

  • Introduction made by the COI directly (warm, named) to a member of the Next Mile team
  • Recorded in HubSpot with COI as the source attribution at the moment of contact creation
  • Seller progresses through Stage 02 Education or beyond before referral attribution is finalized
  • Referral agreement executed by the COI before the first introduction is acted on
Wally's Framing

"I want COIs to feel excited about the ability of what we can do for their clients, and the fact that they can make 20% of the fee could be significant."

Wally Brauer · Managing Partner · COI Program design call · Mar 16, 2026
Open Sub-Item

Gifting protocol.

Concept agreed Mar 30, 2026: handwritten thank-you note plus a small personalized gift for every COI introduction. Specific item, budget, and fulfillment owner are still TBD. Define before the first COI referral comes in. Owner: TBD.

Appendix A · Resolved Mar 16, 2026
✓ Solved

Subscription & M&A Fee Schedule.

Two-track fee model. Track A is the headline sell-side advisory engagement. Track B is the optional subscription/portal that keeps Stage 02 Education relationships warm without forcing premature commitment.

Track A · M&A Success Fee

Greater of, at close.

  • 1% of TTM revenue, or
  • 3.5% of EV up to $30M + 2% of EV above $30M

Whichever produces the higher Next Mile fee at close. Lehman Scale (Double) under discussion as alternative structure for certain deal profiles. No large upfront retainer, no LOI-stage fees, success-aligned at close.

Track B · Subscription & Portal

Three monthly tiers.

  • $500/mo · Portal Growth Program · entry-tier educational access
  • $1,000/mo · Mid-tier consulting access
  • $4,000/mo · Full consulting + portal access

Designed for owners who are early-stage, exploring, or not yet ready to engage on full M&A. Provides a relationship structure during Stage 02 Education without requiring an exclusivity agreement.

$20M–$150M+
Target Deal Size Band
~$40M
3-Year Avg Deal Size Goal
12 / yr
3-Year Closed-Deal Target
Appendix A · Resolved
✓ Solved

Geographic Focus.

Decision: no geographic restriction. Next Mile serves T&L sellers across North America. The Southeast was raised as a possible focus; conclusion was that artificial geographic constraints would limit pipeline without a corresponding gain in service quality.

Rationale

Why no restriction.

  • T&L is a national industry with national buyer pools; geographic boundaries don't track to buyer behavior
  • Mike and Wally have national operating relationships from prior careers; constraining to one region forfeits that
  • The 300+ buyer database is national-scale; matching is sector-specific, not geography-specific
  • Southeast pipeline can still be a focused activation area without becoming an exclusive operating zone
Appendix B · Resolved
✓ Solved

CRM & Hosting Decision.

Two infrastructure decisions resolved together. CRM stack consolidates around HubSpot. Website hosting stays on WordPress in the near term, with HubSpot CMS recommended for v2.

CRM

HubSpot Marketing Pro + Sales build.

HubSpot Marketing Pro is the campaign and contact management platform. WhatConverts integrated for call tracking. Mike's homegrown CRM is being retired into HubSpot.

Second Mile (Sara Wolfe Vaughan) delivered the HubSpot Marketing Pro setup and the TIA email campaigns. Spoke Marketing (Ciara Brewer) is now building the HubSpot Sales Hub — mapping the 10-stage Buyer Journey to Sales pipeline stages with custom properties for source attribution, COI referrer tracking, and deal-stage progression (per Phase 2 Build SOW, Apr 30, 2026).

Website & CMS

WordPress now. HubSpot CMS for v2.

Option A · WordPress: current platform. Stays in place through 2026 to avoid disrupting active campaigns. Lower switching cost in the short term.

Option B · HubSpot CMS: recommended migration target for v2. Native CRM integration, attribution continuity, and unified content + automation reduce platform fragmentation. Migration trigger: Q1 2027 or earlier if WordPress maintenance burden exceeds capacity.

Appendix A · Resolved
✓ Solved

Foundation Step 01 · Alignment & ICP.

The first foundation step in the Revenue Execution System build. Defined the ICP (Hero's Journey · Chapter 1), the COI categories, and the leadership alignment that everything downstream depends on.

What was decided

Six anchor decisions.

  • Hero's Journey narrative framework (Story on Purpose) · the foundation everything downstream built on · Setup / Proof / Invitation structure carrying every play
  • ICP: founder-led T&L · $20M–$150M+ revenue · owner 55+ · ethically driven
  • Sectors: asset-heavy carriers, asset-lite brokers, warehousing operators
  • Geographic scope: North America, no exclusion (Southeast watched, not enforced)
  • COI categories: 5 tiers, 36 vendors mapped (see COIs tab)
  • Operating cadence: bi-weekly Tuesday meeting, document is the living agenda

This foundation is the basis for every subsequent play, every campaign, and every Buyer Journey stage definition. When something downstream doesn't track, we revisit Foundation 01.

Active Initiative · Spoke Marketing Build
Project Underway

HubSpot Sales Hub Build.

Ciara Brewer / Spoke Marketing is the active sales-side build partner, replacing Sara / Second Mile for this scope. Sara delivered the Marketing Hub setup and TIA email campaigns; Ciara now leads the HubSpot Sales Hub stand-up per the May 26, 2026 quote (Reference 20260526-064400744). Build window: 6 weeks from kickoff May 27 through full system live Jun 30, 2026.

Why this matters

Stage data is the dashboard.

Until the HubSpot Sales Hub is live, every "X accounts in Stage Y" number in this document reads TBD. The Buyer Journey board, the pipeline summary, and the play-level pipelines all depend on accurate stage data.

Once live, the board becomes a real-time operational view, not a reporting artifact.

Partner transition · Sara → Ciara

Marketing built. Sales next.

Sara Wolfe Vaughan / Second Mile delivered the foundation: HubSpot Marketing Pro setup, segments, templates, and the full 9-segment TIA email campaign before, during, and after the show. That work is complete.

Ciara Brewer / Spoke Marketing takes the build forward into Sales Hub: 10-stage pipeline, custom properties, post-TIA contact triage (53 contacts), Mike's CRM migration, and Wally + Mike training as the system goes live.

Stage-to-System Mapping Call

The next checkpoint.

Open item: schedule Stage-to-System Mapping Call (Mike + Ciara + Dan) to walk through each of the 10 Buyer Journey stages and confirm the HubSpot field structure, custom properties, automation triggers, and attribution model. Embedded in the Phase 2 Build kickoff per Spoke Marketing SOW. Until this call lands, the build is partially blocked on shared definitions.

Active Decision · For next meeting
Decision Pending

Spoke Marketing · HubSpot Sales Pro Set Up.

The May 26, 2026 quote in front of leadership for HubSpot Sales Hub stand-up and the first two months of active support. Reference 20260526-064400744. Prepared by Ciara Brewer, Spoke Marketing. Target kickoff: May 27, 2026. Full system live: Jun 30, 2026.

Investment summary

$15,000 all-in for 60 days.

  • HubSpot Sales Hub Implementation · Growth: $14,000 (one-time)
  • HubSpot Training & Support · Active: $3,000/mo × 2 = $6,000
  • One-time subtotal: $20,000
  • Strategic Partner Discount (25%): —$5,000
  • Total: $15,000

Payment schedule: $7,500 due on receipt · $7,500 due Jun 30, 2026. ACH preferred.

Assumption: Sales Pro upgrade required. Pro-dependent line items below are marked with an asterisk (*) and build immediately upon upgrade confirmation.

Why Spoke · Why now

Two different jobs. Two different specialists.

Second Mile (Sara Wolfe Vaughan) delivered the HubSpot Marketing Hub setup and the full 9-segment TIA campaign. That was their lane — marketing automation is their specialty, and the work is done.

Spoke Marketing (Ciara Brewer) leads on the CRM and Sales Hub side. Different specialty, different scope. The handoff is a vendor change by design, not a replacement.

Why the Training & Support is included

System + people, together.

A pure Build-and-leave engagement risks leaving Mike and Wally with a system they don’t operate in. Two months of Active Training & Support keeps Ciara in the seat with both of them through cutover and into steady state.

Includes 4 training sessions + 30-min weekly office hours for the first 60 days, covering 2 Sales Pro seats.

Scope · What gets built

Six categories · Pro items marked.

Lead pipeline: Lead status configuration (Cold, Contacted, Engaged, Qualified, Portal, Disqualified) · visual lead pipeline board as a second workspace separate from the deal pipeline* · contact list views by lead status for daily queue management · automated lead scoring* (behavior-based triggers advance contacts through stages automatically) · portal contacts identified and tagged from existing database.

Deal pipeline: 10-stage deal pipeline (Engagement through Alumni with close probabilities) · active deal records created from CRM field map and Dan’s stage notes · lead-to-deal handoff* (qualified contact triggers deal record creation at Stage 1 automatically).

CRM configuration: Custom contact properties (Contact Type, COI Tier, EBITDA Adj, CIM Status, LOI Signed Date, Exclusivity Expiry, NDA Sent, NDA Signed, Referral Count) · company and contact object setup (T&L business at company level, owner at contact level) · up to 3 custom record layouts configured per user role.

Database segmentation: Lead routing workflows (inbound form routing and stage-advance task triggers) · bounce cleanup and email deduplication pass.

Sales tools: 4 email templates (Seller outreach, COI outreach, follow-up, break-up) · automated sequences* (Seller 1A 4-touch cold cadence, COI 2A quarterly drip, form auto-response, break-up sequence) · playbooks* (stage-level task checklists per pipeline stage covering pre-call research, discovery questions, go/no-go, and objection handling) · document library with link tracking (COI one-pager, Next Mile one-pager, RES overview) · built-in calling with automatic call logging*.

Reporting and dashboards: Basic pipeline report (stages, weighted value, lead source) · full dashboard suite* (Wally’s daily activity dashboard, Mike’s pipeline dashboard, lead source attribution scoreboard).

Training and onboarding: 2 Sales Pro seats · 4 training sessions · 30-minute weekly office hours for the first 60 days.

Mike-first 6-week schedule

The new build cadence.

  • Wk 1 (May 27): Pre-kickoff gates (SOW, Sales Pro approval, field map & active deals to Ciara, TIA list + campaign map). Mike’s foundation built in parallel: custom properties, 10-stage deal pipeline, up to 3 record layouts, active deals imported, lead status configured, bounce cleanup. Mike training 1 (deal board).
  • Wk 2 (Jun 2) · ♦ Mike cutover sign-off: 4 email templates, document library + link tracking, lead routing workflows, contact list views, portal contacts tagged. Pro items: visual lead pipeline board*, lead-to-deal handoff*. Mike training 2 (daily workflow) · Wally training 1 (contact entry).
  • Wks 3 – 4 (Jun 9 – Jun 16) · ♦ Wally operational: Database segmentation, company + contact object setup, basic pipeline report. Pro items: automated sequences*, lead scoring*, playbooks*. Wally training 2 (sequences*) · both training 4 (playbooks*).
  • Wks 5 – 6 (Jun 23 – Jun 30) · ♦ Full system live: Full dashboard suite* (Wally’s daily activity, Mike’s pipeline, lead source attribution). Steady state begins.
  • Through Week 6 and beyond: 30-min weekly office hours for both Mike + Wally across the full 60 days.
Out of scope · Phase 3

What this quote does not cover.

  • Buyer campaign activation (3A / 3B / 3C sequences)
  • Landing pages
  • Portal ↔ HubSpot integration

All three are deferred to Phase 3, scoped separately after cutover.

Notes from the quote

Working assumptions.

  • Two rounds of revisions per deliverable included. Additional revisions billed at $200/hr.
  • 30-day acceptance window after each deliverable.
  • Termination: 30-day notice from either party, work-to-date billed on exit.
  • Quote expires: Aug 24, 2026.
B

Brand Assets

Named collateral pieces produced and in production for the firm. Each one referenced from a play within the playbook; this is where the asset itself lives or is scoped.

Collateral · Used at TIA Apr 15
Live Asset

TIA Handout · The T&L Owner's Journey.

Customer-facing two-pager distributed at TIA Booth #218 (Apr 15). Frames the 5-stage T&L ownership lifecycle and 6 mindset triggers that open the exit window. Doubles as a conversation starter for COIs and as the seller-facing positioning piece. Pairs with the free Exit Readiness Scorecard (3-min self-assessment).

5 Stages of Ownership

Where the owner is on the map.

  • 01 Launch & Traction: "Prove it works. Build the machine." Owner is the business.
  • 02 Growth: "How big can we get?" Leadership team forms.
  • 03 Maturity: "Is this still fun? What's next for me?" Risk/reward shifts.
  • 04 Peak Value: "The business runs without me. Now what?" Maximum valuation. Owners who exit here leave the least on the table.
  • 05 Active Process: "Don't screw this up." 12-24 months to close.
6 Mindset Triggers

What opens the exit window.

  • The Growth Ceiling (need capital or strategic partner)
  • The Burnout & Fatigue ("I just want a real vacation")
  • The Succession Gap (next generation can't or won't take over)
  • The Partner Dynamic (forced liquidity event)
  • The Peer Exit ("what is mine worth?")
  • The Industry Event (TIA itself often is one)
How it feeds the engine

Where this shows up.

The 5-stage frame and 6 triggers are conceptual content reused across Sellers (Cold Targeted intro and Engaged Early nurture) and COIs ("how to spot the right client"). The Exit Readiness Scorecard QR routes to the same diagnostic that lives inside the Portal as the readiness assessment. Mapped to John's library titles "Is Your Transportation Business Ready to Sell?" and "Timeline: Planning Your Exit 12-24 Months Out."

Collateral · COI Program
Live Asset

COI One-Pager · Partner With Us.

Customer-facing two-pager built at Wally's request via John (Manus). The COI-side proof point: who Next Mile is, why this partnership works, how to spot the right client, the handoff script. Used in Targeted drip and post-conversation follow-up; co-brandable for Engaged COIs.

Headline numbers

Why a COI trusts us.

  • 90+ successful exits
  • 90+ years combined T&L experience
  • $20M+ revenue sweet spot
  • 100% sell-side only
Why the partnership works

Four reasons for the COI.

  • You become the trusted advisor
  • Co-branded content for your clients (Exit Library + Scorecard under their brand)
  • No disruption to your relationship — we work quietly alongside
  • 20% referral compensation on closed transactions
How to spot the right client · 4 questions

The qualifier.

  • "How long have you been working with this owner?" → 5+ years, direct owner relationship
  • "Do you talk to the owner directly, or mostly to their team?" → direct access, owner trusts them
  • "Has the owner ever mentioned what's next for the business?" → succession, fatigue, growth ceiling, partner tension
  • "Is the business running without the owner needing to be there daily?" → Stage 4 / Peak Value signal
The handoff script

"I know a couple of guys at Next Mile M&A who work exclusively with T&L owners — no pitch, no pressure. They just love sharing stories from the industry and talking through what owners are thinking about. Would your client be open to a quick Zoom call? It's genuinely just a conversation."

COI One-Pager · Handoff Script
How it feeds the engine

Where this shows up.

This is the headline collateral for COIs tab. Lives in HubSpot's document library (per Spoke Marketing SOW Phase 2 Build) so Wally can attach it directly to outreach with link tracking. Used in Targeted drip, follow-up after first conversation, and as a co-brandable asset for Engaged COIs (with permission).

Appendix · Brand Asset Inventory · From Calibration
Reference

Brand Assets Identified · From the Calibration.

Seven collateral pieces surfaced as gaps during the Phase 1 calibration. Listed by priority based on what would most unblock the active playbook. Each is referenced by one or more O&O entries (#24 and #26 specifically).

BA1 · HIGHEST PRIORITY

Blind Seller Teaser (one-pager).

Why: Single biggest tactical gap from the COI calls. Wally surfaced the need twice on Call-03 (Tenstreet). What it is: One-page anonymous summary — industry standard, mode, revenue band, GP%, customer concentration, geography. Built from the SIM but heavily redacted. Owner: TBD (John for content, Natalie Nicole for template). Lives in: HubSpot document library + COIs · Campaigns & Assets. Cross-ref: O&O #26.

BA2

Mid-Length Operator Pitch (2–3 min).

Why: Mike's full bio ran 6 min on Tenstreet, ~3 min on Armstrong. Playbook has the 30-Second Conversation and the full biography — nothing in between. Owner: Mike (draft) + Wally (review). Lives in: Sellers + COIs · Messages & Narrative. Cross-ref: O&O #24.

BA3

The Wally Exit Story · Canonical Version.

Why: Already operating as peer-credibility unlock. Belongs documented in three formats. Full version (~7 min): what Wally told Chad on Call-02 (Apr 17, min 10:54–18:06). Structural fragment (~90 sec): what Wally invoked on Call-06 with Travis (Apr 3, min 30:46). Single-sentence positioning: "as a previous transportation owner that I am" — the recognition phrase. Owner: Wally. Lives in: Sellers · Messages & Narrative. Cross-ref: O&O #24.

BA4

The "Live Valuation Revision" Story.

Why: Captures the analytics value proposition concretely. What it is: Anonymized case study — Q1 trend data revised EV from $20.5M to $27.7M in 90 seconds on a live call. Demonstrates proprietary analytics in action. Owner: Mike (data) + Natalie Nicole / John (format). Lives in: Pitch deck, website case studies, Sellers · Campaigns & Assets. Cross-ref: O&O #24.

BA5

The 30-Second Conversation · Confirm or Refine.

Why: Already in playbook (per Vol. 1 No. 1). Calibration data suggests Mike rarely delivered it in the 30-second form — the operator biography ran long. Worth pressure-testing whether the canonical version is real or aspirational. Owner: Mike + Wally (test). Lives in: COIs · Messages & Narrative.

BA6

The COI Directionality Visual.

Why: If O&O #25 lands as a decision, team needs a clean visual distinguishing sell-side / buy-side / bidirectional COIs. Owner: Natalie Nicole (design). Lives in: COIs · Overview. Cross-ref: O&O #25.

BA7

Tenstreet Handoff Protocol · Documented.

Why: Kevin laid out a clear referral mechanic on Call-03: ping Kevin → Teams to Tim Crawford → intro to Tim + Shannon Wheeler → Kevin steps back. Gold for PE-backed strategic acquirer COI patterns generally — not just Tenstreet-specific. Owner: Wally (relationship owner). Lives in: COIs · Conversation (handoff patterns).

Appendix B · Long-form Article · May 26, 2026
Live Asset

The Top Ways Transportation M&A Deals Get Blown Up.

Anchored in Mike’s process. The four places transportation M&A deals consistently fall apart: financial errors that compound under a multiple, operational data that TMS systems can’t present, problems that arrive without warning (legal, customer, time), and the seller’s own state of mind after an LOI lands. Closes with a real case study: a seller with growing gross profit concentration that would have been a buyer’s renegotiation lever — surfaced from day one, presented monthly, so when the buyer raised it in diligence the basis for renegotiating collapsed. Deal closed on the terms agreed.

The Four Failure Points

Financial · Operational · External · Mental.

Financial errors & variances. Trailing 12-month EBITDA moves every month. Add-backs roll off; a $250K personal premium aging out of the window at a 5x multiple costs $1.25M of valuation. Data built for accounting purposes, not for buyers.

The operational data TMS can’t tell a buyer. Naming conventions create false diversification. Revenue growth from length-of-haul or rate spikes that don’t reflect underlying productivity. Gross profit concentration that grows while in the process.

Where Deals Renegotiate

Problems that arrive without warning.

Legal & safety exposure. A mid-process lawsuit or safety event can collapse a deal or force escrow/earnout renegotiation. Disclosure timing creates trust problems beyond the specific issue.

Customer instability. A top customer entering distress or being acquired mid-process changes the buyer’s view of the business entirely.

Time compounding. 6–9+ month diligence cycles mean any of the above can emerge, develop, or compound. A deal that would close cleanly at month four can look different at month eight.

The Seller’s State of Mind

The number in your head after the LOI.

Once a number is on a document, it becomes the reference point. Legitimate diligence findings that move the valuation produce reactions that aren’t rational. Second-guessing on positive momentum mid-process. Running the business at full capacity while running the transaction. Wally on seller emotions: “They are going to have emotions. For us to tell them they’re not is just not truthful. Different people have different types of emotions for different types of reasons. But they’re all real from that seller’s perspective.”

The Closing Argument

Remove the leverage before it’s used.

The sellers who close on the terms they were offered went to market with clean data, an honest risk picture, and people who had been through it. The case study: gross profit concentration identified before market, documented, presented to every buyer from the start, sent monthly. Buyer surfaces it in diligence — the response is the report from day one. Basis for renegotiation collapses. Deal closes on agreed terms.

Use: nurture spine for the next campaign cycle. Engaged-not-ready sellers, COIs (attorneys/insurance/finance), cold targeted list. Anchor of broader content sequence; next piece in the library is on seller fatigue.

URL: nextmilema.com/the-top-ways-transportation-ma-deals-get-blown-up/

C

Call Summaries

Source material from the recorded-call analysis loop. Each card captures one call: who, when, what worked, what surfaced, what feeds back into the playbook. Phase 1 calibration delivered five summaries — three Seller calls and two COI calls.

Appendix · Call Summary · Apr 2, 2026
Reference

Call 01 · UTS · Bruce Parsons.

Seller call. ~60 minutes. Stage Evaluation → Preparation. Mike + Wally on Next Mile side. Substantial soft-side / culture-fit conversation. Bruce came in with prior M&A scarring (3 transactions + 1 acqhire, "Texas was a mess"). The conversation went further than the framing suggested — this was not a meet-and-greet, it was deep evaluation.

Seller Profile

Culture-first founder.

LTL / asset-based trucking. "I am nobody from nowhere. The bigger we get, the smaller I feel." Father worked too hard, didn't leave money — Bruce values balance for his team. Motivation: protect what he built, not headcount growth. Has acquired and integrated three companies + one acqhire (Charlotte, Chicago, Texas). Sees acquisition as a sports-team metaphor: "You got your starters, you got your second string."

What Worked

Soft-side framing resonated.

Mike's and Wally's emphasis on personalities, cultures, skill sets, care — landed with Bruce. His responses were lengthy, personal, emotionally grounded. Wes's AI-narrative functioning as objection pre-empt for "M&A has gone poorly before."

Data Quality Flag

Multiple UTS-Bruce transcript files exist in Drive (7 visible in May 22 screenshots). Whether these are duplicates from the rebrand naming change (Black Belt TC → Next Mile M&A) or distinct sessions is unresolved. Full Call-01 analysis may be incomplete pending resolution.

Appendix · Call Summary · Apr 17, 2026
Reference

Call 02 · Freight Logistics · Chad & Jeff.

Seller call. ~65 minutes. Stage Education → Evaluation. Mike + Wally + Ron on Next Mile side. Chad has a competing LOI from Dynamic Connections (via Copper Run intro). This call is the live "alternative-to-single-buyer" pitch in action. Wally's full exit story (~7 min from min 10:54) was the central trust-builder.

Seller Profile

Lifestyle / baton-handoff.

Non-asset, multi-modal niche. ~$7M revenue, $1.9M GP, 33% margin, $825K owner draws. No TMS system. 5 employees including Chad (60) + Jeff (60, 40% owner, 23-year partnership starting in high school). Customers since 1990 still active. Motivation: "We don't want to keep working the rest of our lives. We don't really have a succession planned."

What Worked

Wally's exit story + live comparable.

Wally's full exit narrative landed. Mike's reference to the current Denver seller with 8 interested buyers landed as proof of buyer-database depth. The "no TMS" structural issue handled gracefully — Mike: "We have sold some companies that could not generate TMS data."

Active Buyer Context

Dynamic Connections (DTS, Toronto) presented an unsigned LOI March 19. Steve Frankhill (PE guy, Internal PE backing out of Chicago) + Greg Dark are the buyer-side principals. Mike knows the company well — "they took a look at one of our current sellers." The Denver-based current Next Mile seller has 8 interested buyers from TIA — potential alternative for Chad if FL fits any of them.

Appendix · Call Summary · May 12, 2026
Reference

Call 03 · Tenstreet · Kevin Nadeau.

COI call. ~53 minutes. First documented end-to-end execution of the TIA → post-show 20-min commit motion. Kevin volunteered a referral mid-call (the hardware-based transportation tech opportunity) after the 20% fee disclosure landed. Bidirectional relationship — Tenstreet itself is an acquirer (~2 deals/year).

COI Profile

Operator-vendor + strategic acquirer.

Tenstreet: largest ATS in transportation (~5,000 trucking clients), 20 years old, PE-backed (Providence Equity), ~500K monthly active drivers on Driver Pulse mobile app. Kevin: 30 years industry, founder of True Load Time (exited to Tenstreet 4 years ago), now senior leadership + strategy / partnerships / M&A scouting. Decision chain above Kevin: Tim Crawford (CEO/co-founder), Brian Riddle (co-founder, tech), Shannon Wheeler (in-house counsel).

What Worked

Operator credibility + disclosure timing.

Mike's full operator pitch (6 min from min 31:11) landed because Kevin is also an exited founder-operator. 20% fee disclosure timing (min 38:20) was post-rapport — Kevin received it as bonus, not lead. Portal as long-game retention message landed unexpectedly clearly on a COI: "Even if the company owners aren't interested in selling next month..."

Tenstreet Handoff Protocol

Kevin defined the routing mechanic on the call: ping Kevin with vertical / general fit → Kevin pings Tim Crawford via Teams → if interested, intro to Tim + Shannon Wheeler → Kevin steps back. This is gold for PE-backed strategic acquirer COI patterns generally — not just Tenstreet-specific.

Live Referral

At call min 44:05, Kevin volunteered: serial entrepreneur contact, hardware-based transportation tech, ~8-figure ARR, looking to exit to free up capital for new AI venture. Tenstreet passed because they're software-only. Verbal referral, no paperwork — live test case for verbal-first attribution policy (see O&O #28).

Appendix · Call Summary · Apr 21, 2026
Reference · Partial Data

Call 04 · Armstrong & Associates · Evan Armstrong.

COI call. ~12 minutes (truncated). Mike's Zoom connection dropped twice from bandwidth issues. Ron carried the substantive pitch from min 11:14. Call ended with Mike trying to reach Evan by cell phone — substantive partnership conversation likely happened off-recording. Data quality is thin; most findings flagged as needing follow-up.

COI Profile

Market-research authority + buy-side advisor.

Armstrong & Associates: industry-standard market research (top freight broker list, top warehousing list, top lists for Logistics Management magazine, Air Cargo World). ~4,000 company profiles. ~4,000 buy-side outreaches last year. Self-described: "Most of what we do is on the buy side." Currently working 4 active buy-side deals (2 in freight brokerage). Source of intro: Todd (last name unknown — open ID).

What Worked

Ron's process pitch carried when Mike dropped.

Bidirectional complementarity landed fast (min 4:30): "Most of what we do is on the buy side, so it's good to be working with you guys." Ron's pitch (min 11:14) on TMS integration, automated SIMs, vetted financials — first non-Mike credibility carry on a recorded call. Different brand voice than Mike's biography, but it worked.

TIA Sentiment Flag

Evan at min 2:16: "I haven't gone for a few years. I used to speak there and then I just got tired of drinking beer with freight brokers. So I decided not to go. We have three events of our own. So those tend to be more fruitful." One COI disengaged from TIA. One data point. Worth tracking against future COI conversations — if 2–3 more say similar things, TIA channel thesis needs revisiting.

Open Items From This Call

Did the cell-phone follow-up complete? Was 20% fee disclosed? Was bidirectional buy-side / sell-side fit explicitly surfaced? Who is Todd (the introducer)? Without these answers, the relationship status is ambiguous between Tier 2A (first contact) and Tier 2B (engaged after first conversation).

Appendix · Call Summary · Apr 3, 2026
Reference

Call 06 · Xtreme Trucking · Travis & Marty.

Seller call. ~47 minutes. Stage 04 Evaluation — live valuation walk-through with real numbers on screen. Mike struck $20.5M EV initially, revised to $27.7M after Travis surfaced Q1 lift data and Mike re-ran the math live in 90 seconds. Travis verbally committed to next step: "So here we go. Yeah. Let's do it." Household-alignment gate still pending — Travis hadn't told his wife at call's end.

Seller Profile

Identity / next-chapter, experienced acquirer.

Refrigerated, asset-based, Wisconsin. 22–25 local trucks + over-the-road. 100 trailers in local pool. Flat-floor reefers, TK thermal pings, Great Dane brand (premium resale spec). Cayman-domiciled captive insurance ($1.8M value). Travis: 41 years old, "I need to have some sort of purpose." Has bought 6 companies — experienced acquirer. Knows earn-outs, employee retention risk, deal structure.

Financials Established On Call

TTM EBITDA $3.4M → $4.2M.

Initial: $3.4M EBITDA × 5–6x multiple = $20.5M EV. Owned net property ~$1M. Captive insurance $1.8M. After Q1 lift: +$450K/month positive trend through Jan–Feb → +$700K floor adjustment → ~$4.2M revised EBITDA → $27.7M EV. Cash at close estimated 70% (favorable risk profile, refrigerated mode). 2-year earn-out typical. Platform-company candidate.

What Worked · The Diagnostic Posture Validated

Travis at min 25:03 explicitly named Mike's pushback as the right posture: "That's why early on in this call, when I kind of pushed back, I'm like, hey, we are doing a lot of things to make changes in our network and our margin improvements. And I think you responded well, every owner says that and thinks the market's going to save them. But we're actually doing some hard stuff out there grinding to fix what we have." This is the cleanest validation of the Doug Hazen 2022 posture — four years apart, same response.

Ron's First Analyst Moment

Min 18:59 — Ron interjected with a technically correct, well-timed question on captive-insurance equity treatment: "On the margin, if he's been pumping sort of equity into the captive, will that come back as a normalized expense? Because someone else could technically have a lower insurance expense going forward if they weren't sort of beefing up their captive equity?" First documented analyst-seat moment on a recorded prospect call. Validates the Mike-Wally-Ron division of labor (O&O #30).

Wally's Household-Alignment Coaching

"How do you think she'll respond, Travis? ... That's why you've been the success you have, brother. Don't ever — Seriously, you're only as good as your wife, so make sure she knows that."

Wally Brauer · min 43:46–44:11 · Apr 3, 2026

Operator-to-operator coaching that a banker M&A advisor cannot deliver. Belongs in the playbook as canonical script for the Stage 04 household-alignment moment (see O&O #22).

D

Matrices & Frameworks

Side-by-side comparison reference. Surfaces the patterns across multiple calls that anchor the framework-level O&O entries (#20 Experienced Acquirer dimension, #21 Motivation archetypes, #25 COI archetype widening, #29 Bidirectional COI tracking).

Appendix · Seller Matrix · Phase 1 Calibration
Reference

Seller Matrix · Side-by-Side.

The three sellers analyzed in Phase 1, compared on financial and qualitative dimensions. Surfaces the patterns that anchor O&O #20 (Experienced Acquirer Dimension) and #21 (Motivation Archetypes). "—" means not on transcript record; "(need)" means partial data, worth chasing.

Dimension Bruce / UTS Chad / Freight Logistics Travis / Xtreme
Age 60 41
Mode LTL / asset-based trucking Multi-modal non-asset (ocean, customs, reverse logistics, e-waste) Refrigerated asset-based + local
Revenue (need) ~$7M Implied $20M+ EV basis
Gross margin (need) 33% (need)
EBITDA (need) ~$825K owner draws (approx) $3.4M → $4.2M revised
Strike EV (none yet on transcript) Competing LOI from DTS (terms undisclosed) $20.5M → $27.7M live revision
Multiple (need) In assessment 5–6x
Acquisition experience 3 transactions + 1 acqhire (as buyer) None 6 acquisitions (as buyer)
Motivation archetype Legacy / Culture-protector Lifestyle / Baton-handoff Identity / Next-chapter
Exit type sought (under exploration) 100% sale, open to second bite Open to both; platform-co candidate
Spouse / co-decider status Co-decision w/ Jeff (40% partner, 23 yrs) Hadn't told wife at call end
Tech / operational stack Custom-built software (Wes / Bruce technology) No TMS — manual ops Standard TMS, sophisticated equipment spec
Stage at call Evaluation → Preparation Education → Evaluation Stage 04 Evaluation — complete analytical, pending household
Stickiest line "I am nobody from nowhere" "Hand the baton off" "I need to have some sort of purpose"
What This Matrix Surfaces

Three sellers, three motivations, three acquisition-experience levels — same engagement-tier framework can't capture all of it. Supports O&O #20 (add Experienced Acquirer dimension) and O&O #21 (document Motivation archetypes). Empty cells ("—" and "(need)") are the work list for the next round of seller intake — the dimensions we don't currently capture but should.

Appendix · COI Matrix · Phase 1 Calibration
Reference

COI Matrix · Side-by-Side.

The two COIs analyzed in Phase 1, compared on archetype and operational dimensions. Surfaces the patterns that anchor O&O #25 (COI Archetype Framework) and #29 (Directional Tracking). Note: only 2 COI calls in calibration set; matrix should expand as more COI calls come in.

Dimension Kevin / Tenstreet Evan / Armstrong
COI archetype Operator-vendor + strategic acquirer + network-density node Market-research authority + buy-side M&A advisor
Canonical category? No (not attorney/CPA/banker/wealth mgr/insurance) No (not attorney/CPA/banker/wealth mgr/insurance)
Source of intro TIA Capital Ideas floor (Apr 15, 2026) Todd (last name unknown — open ID)
Directionality Bidirectional (refers sellers + Tenstreet is an acquirer) Bidirectional (refers sellers + represents buyers via buy-side advisory)
Network density Very high — ~5,000 trucking clients, ~500K monthly active drivers, hosts ~500-client user conference Very high — ~4,000 company profiles, ~4,000 buy-side outreaches/year, industry-standard top-list publisher
Decision authority Limited — routes to Tim Crawford (CEO) + Shannon Wheeler (counsel) Owns the firm
Current acquirer appetite ~2 acquisitions/year, constrained near-term by internal AI focus 4 active buy-side deals (2 in freight brokerage)
20% fee disclosed? Yes (min 38:20, post-rapport) — received as bonus, not lead Not on recording (likely off-call follow-up)
Structured ask asked? No No
Live referral surfaced? Yes (hardware deal, min 44:05) — volunteered No (4 buy-side mandates not surfaced as buyer-database matches)
TIA sentiment Active attendee, met Mike/Wally there Disengaged"tired of drinking beer with freight brokers"
Tier classification 2B trending to 2C (volunteered referral + handoff protocol agreed) 2A (first contact, partnership-fit conversation incomplete due to truncation)
What This Matrix Surfaces

Both COIs analyzed are non-canonical (not in the Mar 16 canonical list) and bidirectional (refer sellers AND represent buyers). This is the data anchoring O&O #25 (widen archetype framework) and O&O #29 (HubSpot directional tracking). Sample size is small — only 2 COI calls — so the framework recommendations are directional, not definitive. Worth expanding the matrix as Phase 2 brings more COI calls in.

E

Cut Field Notes

Content deliberately removed from the main playbook but preserved here as institutional memory. Knowing what we considered and chose not to include is part of the institutional record.

Appendix B · Cut from Vol. 1 No. 1 · May 22, 2026
✂ Cut Content

The TIA Recap field note.

Originally the lead field note on the Overview tab. Replaced in Vol. 1 No. 1 by "Post-TIA Conversion Wave" because the recap content was overtaken by the actual conversion activity it predicted. The 53-contact summary still appears in Stage 01 Who's Here and the Playbook header data. Preserved here in case anyone wants the original framing.

Original eyebrow

The TIA Recap.

Title: "53 contacts, three audiences, one campaign."

The April 15 TIA Capital Ideas Conference in Phoenix is in the rearview. The 9-segment HubSpot campaign ran live across pre-show, at-show, and post-show waves. Post-show load: 53 contacts (12 Sellers, 6 Buyers, 35 COIs) imported into HubSpot, segmented, and queued for follow-up. Wally and Mike have an active queue waiting for them in Week 1 of the Spoke build.

Linked to: The Playbook · Stage 01 Prospecting

Why it was cut

Overtaken by the conversion activity.

By the May 12 leadership call, the post-TIA cohort had produced 5+ named seller conversations in active motion. The story shifted from "53 contacts loaded" to "the flywheel is producing." The replacement field note carries that newer story.

Restoration trigger: if a future issue wants a reset summary of TIA outputs, this framing is the canonical reference.

Appendix B · Cut from Vol. 1 No. 1 · May 22, 2026
✂ Cut Content

The Regulatory Shock field note.

Originally the third field note on the Overview tab. Replaced in Vol. 1 No. 1 by "First COI-Sourced Deal Flow." The regulatory development is still real and worth tracking, but it lives more naturally in the COIs tab (Howden notes) than as a front-of-book headline. Preserved here for the original framing and the reasoning.

Original eyebrow

The Regulatory Shock.

Title: "A Supreme Court ruling redraws the freight broker map."

A substantive development surfaced in the Howden Group meeting: the Supreme Court's recent decision against C.H. Robinson eliminates the preemption defense for freight brokers. The downstream effect could push smaller brokers out of business or into the market. For Next Mile, this is a potential new trigger — owners considering an exit they hadn't been considering eight weeks ago. Worth watching as a new Open Moment in the seller-side framework.

Linked to: COIs · Howden partnership notes

Why it was cut

External-trigger watch, not headline.

By May, the C.H. Robinson decision was 8+ weeks old. The "new" framing read stale. The downstream effect on smaller brokers is real and worth tracking, but as a slow-burn industry tailwind, not a Three Things to Know item. Field Notes work best when they describe something that shifted in the prior two weeks.

Restoration trigger: if a quarterly review wants to recap the macro tailwinds shaping seller pipeline, this is the source.

Reserved
Awaiting resolution

Future archives.

As Define and Discuss items from The Meeting tab resolve, their full context lands here. Likely next archives: Gifting Protocol (once defined), 1-Year Goal Cascade (once leadership session lands), Math Inconsistency Resolution (once 12-deal target is reconciled with 2 LOIs/qtr × 90% close rate), Trademark/Copyright outcome, Mike + Wally Pipeline Update format, Portal & AI strategy decisions, Buyers Database migration plan.

Section F
CRM Build · HubSpot foundation + property architecture

CRM Build.

The HubSpot foundation layer — what’s being built, what’s blocked, and how data is structured. Ciara Brewer (Spoke Marketing, Integrator + Account Director) leads the build. This section captures the latest status, the contact and deal architecture, and the lead status definitions so the leadership team can review what’s in flight without depending on a status meeting.

Appendix F · Status Update · Jun 8, 2026
Active

Foundation Layer · Status email from Ciara.

From Ciara Brewer (Spoke Marketing) to Dan, June 8, 3:11 PM. Confirms foundation layer ships by Wednesday June 11; flags database segmentation as the active block.

By Wednesday, the foundation layer will be fully in:

  • Lead Status stages configured
  • Deal Pipeline built
  • All custom contact properties live
  • Record layouts set up for both users
  • Bounce cleanup done

Blocked: database segmentation — tagging Seller, COI, and Buyer across the existing contacts.

Right now we have a company field that is “Buyer, Seller, or General.” We have 341 companies marked as Buyer or Seller. Does this need to be a contact value as well? Which contacts should be COI?

A few things needed from your side to keep the build on track:

  • Signed SOW + billing address for the deposit
  • Confirmation on the HubSpot quote so the Sales Pro upgrade can be finalized: sequences, the visual lead board, and the automation layer are all dependent on that
  • Al’s pull from Mike’s Access file: once active deal records arrive they can be loaded into the pipeline before Wednesday
  • A window to get Mike on a call for the data download session

Framing for the O&O: the foundation is in and we’re mid-segmentation. Mike can be operational in HubSpot within a week of the SOW being signed and Pro confirmed.

— Ciara Brewer | Integrator + Account Director | 725 Kingsland Avenue Suite 100, No. 8, St. Louis, MO 63130 | M: 773.672.9185

Appendix F · Property Architecture · HubSpot
Reference

Next Mile HubSpot · Property Architecture.

Three objects: Company, Contact, Deal. Each tracks a different layer of the relationship — Company holds persistent business facts, Contact holds role, Deal holds transaction state.

Company object

Facts about the T&L business · persistent, transaction-independent

Property Type Values
Company TypeDropdownSeller, Buyer
Asset TypeDropdownAsset-Based, Asset-Lite, Non-Asset
EBITDA AdjNumberCurrency
Annual RevenueNumberNative field

Contact object

Facts about the person · role in the relationship, not the transaction

Property Type Values
Contact RoleDropdownSeller, COI, Buyer, Alumni
Lead StatusDropdownNative field — reconfigured (see below)
COI CategoryDropdownInsurance, Finance, Legal, Staffing, Data/Compliance, Freight Tech, TMS
COI TierDropdown1, 2, 3, 4, 5
Referral CountNumberInteger

Deal object

Facts about the transaction · specific to one engagement, can repeat per company

Property Type Values / Notes
NDA StatusDropdownNot Sent, Sent — Awaiting Signature, Signed
CIM StatusDropdownNot Started, In Review, Approved
LOI Signed DateDateTriggers Exclusivity Expiry calculation
Exclusivity ExpiryDateAuto-calculated: LOI Signed Date + 60 days
Deal AmountNumberNative field
Close DateDateNative field
Lead SourceDropdownNative field
Pipeline StageDropdownNative field — 8 stages

Contact Lead Status

Pre-deal qualification · lives on contact record

Status Description
ColdIn the database, never contacted. Sourced from ZoomInfo, LinkedIn, or TIA. No outreach has gone out yet.
ContactedOutreach sent, no reply yet. Wally has made at least one touch — email, call, or LinkedIn.
EngagementReplied or responded. A real conversation has started. Wally is working toward a fit call.
EducationHad a fit call, confirmed interest, but timing isn’t right yet. In nurture. Wally checks in quarterly.
Pre-MarketWants to sell but isn’t ready. Actively working with Mike’s portal — sending monthly TMS data, tracking toward a sellable multiple. Long-term hold.
DisqualifiedNot a fit, opted out, or unresponsive after all touches. Archived. No further outreach.

Deal Pipeline

Active transactions only · deal created when contact reaches Engagement and fit call confirms readiness

Stage Probability Exit Criteria
Evaluation25%Engagement agreement signed
Preparation40%CIM Status = Approved, buyer list curated
Market Engagement50%Qualified buyer confirmed, NDA signed, intro Zoom scheduled
Connected65%Multiple IOIs received, field narrowed
LOI80%LOI signed, exclusivity executed
Diligence90%Wire transferred, PA executed
Transition100%90-day review complete, recommendation letter signed

Closed Won — Deal complete · contact Contact Role updates to Alumni

Appendix G

Marketing partners.

The running ledger of marketing & advisory partner engagements. Each row shows who, what scope, what amount, what status, and where in the doc that partner’s work lives. Created in response to Jay’s June 10 ask for a marketing-contracts recap — now a standing reference, updated each cycle.

Brand echo · intentional, not coincidence

Instant Clarity and Constant Clarity appear on the Cover page as framework layers (the 90-Day Revenue Execution Sprint and the ongoing alignment & accountability engagement). They are also the billing names on the Story on Purpose contracts. This is by design — the framework names and the engagement names are the same words because the framework is the engagement.

Story on Purpose
John Knicely + Dan Klein · jointly delivered

The narrative + strategy partnership behind this engine. Three distinct engagements, two complete + one ongoing.

Engagement Period Scope Amount Status
Instant Clarity
90-Day Revenue Execution Sprint
Late 2025 → TIA launch (Apr 2026) Alumni interviews · Hero’s Journey narrative · brand & positioning foundation · ICP & 4-play architecture · Seller tier framework · 11-stage buyer journey · readiness for TIA $24,000 Complete
TIA Show · floor work
Joint travel + COI conversations
April 2026 John + Dan on the floor at TIA Capital Ideas. COI conversations during the show. Live deal-flow signal-capture. $5,000 Complete
Constant Clarity
Ongoing alignment & accountability
Current Bi-weekly Revenue Execution Engine playbook iteration · leadership cadence · ongoing narrative + strategy work · this document $4,500 / month Active

Cross-ref: The narrative work lives in Overview and The Playbook. The bi-weekly cadence runs through The Revenue Meeting. The doc itself is the deliverable.

Spoke Marketing
Ciara Brewer · HubSpot Sales Hub specialist (Sierra delivers)

The CRM stand-up partnership. Phase 2 build of the revenue engine — the Sales Hub layer.

Engagement Period Scope Amount Status
HubSpot Sales Hub stand-up
Phase 2 build · May 26 quote · 6-week cutover
May 27 → Jun 30, 2026 10-stage pipeline build · custom properties · 3 record layouts · email templates · lead routing · Mike-first training · Wally follow-on training · 60-day adoption support $15,000
$7,500 deposit · $7,500 due Jun 30
In Build

Cross-ref: Full SOW + property architecture in Appendix F · CRM Build. Phase 2 timeline in Overview · You Are Here. The Jun 10 invoice ($7,500 deposit) is the one that triggered Jay’s recap ask.

Second Mile
Sara Wolfe Vaughan · HubSpot Marketing Pro specialist

The marketing-layer stand-up partnership. Delivered the HubSpot Marketing Pro setup and the TIA email campaign.

Engagement Period Scope Amount Status
HubSpot Marketing Pro Implementation + Roadmap
Phase 1 · marketing layer build
Mar → Apr 2026 HubSpot Marketing Pro implementation & roadmap engagement · 9-segment TIA email campaign across past clients + TIA attendees + buyers list + LinkedIn + COI tiers · ~3,471 contacts deployed $13,475 Complete

Cross-ref: Vendor transition logged in O&O #32 (Second Mile finished, Spoke begins). Amount confirmed Jun 11.

Natalie Nicole
Independent brand designer

The brand identity partnership. Delivered the Next Mile M&A visual identity and positioning system.

Engagement Period Scope Amount Status
Next Mile M&A brand identity
Phase 1 · brand foundation
Feb → Mar 2026 Brand identity system · positioning · visual language that informs nextmilema.com and all tradeshow materials To verify
Not documented in this playbook
Complete

Honest note: Same as Second Mile — contract amount not currently in this playbook. Confirm and update next cycle.

Running totals (named)
$29,000
Story on Purpose · completed phases
$24K Instant Clarity + $5K TIA show floor work
$13,475
Second Mile · Phase 1 marketing layer
HubSpot Marketing Pro Implementation + Roadmap (complete)
$15,000
Spoke Marketing · Phase 2 build
$7,500 deposit paid · $7,500 due Jun 30
$4,500/mo
Constant Clarity · ongoing
Story on Purpose continued engagement

1 TBD: Natalie Nicole brand identity amount — to confirm and update next cycle.

Completed-phase totals only. Constant Clarity is ongoing at $4,500/month, not added to lump-sum totals.