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
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
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
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.
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.
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 →
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.
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.
The agenda is the structure. The next section is the live deal pipeline — the 15-minute “Discuss Deals” block runs against this view.
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.
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.
After the deals: what owners committed to last meeting and whether it got done.
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.
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.
To-do’s are the outputs. The O&O list is the input — what gets discovered, discussed, and decided next.
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.
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.
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.
Define is the queue. Discuss is the working session. The next section is where the leadership team's active conversation lives.
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).
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.
Discuss leads to decision. The next section holds items the team has talked through and now needs to approve.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Source material captured. Narrative built. Strategy defined. Brand & website launched. Tradeshow materials produced. TIA executed.
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.
All four plays in motion. 12-deal annual cadence.
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.
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.
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.
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.
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.
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.
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.
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.
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."
"They led me straight into a big warm kiss instead of a hard damaging punch."
"You don't know what you don't know. It was really great to have someone in the corner that knew."
"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."
"I wanted them to really be in good hands when we made this transition."
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Below the goal: the math that has to work for the goal to make sense.
The pipeline math. Activity volumes, conversion rates, and the input-output relationship that produces the 3-Year Target.
The full chain. Working backwards from the 3-year target. Some operators are still TBD and need leadership input — flagged below.
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.
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.
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.
And below the math: the scoreboard. What we measure weekly.
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.
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.
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.
Updated bi-weekly · Tuesday cadence. Watch metrics highlighted in ember.
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.
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.
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.
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).
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.
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.
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:
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.
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.
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.
For the sales force. 11 stages from first contact to alumni referral. Three audiences moving through one engine.
The marketing and sales actions that move a record from one stage to the next. Every Spread carries a numbered, audience-tagged play list.
Three audiences move through the same 11 stages: Sellers, COIs, Buyers. Pace and messaging diverge; pipeline structure is shared.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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. |
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
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.
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.
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."
| 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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| Post-TIA · Sellers cohort | 12 contacts (TBD) | — | Wally |
| Post-TIA · Buyers cohort | 6 contacts (TBD) | — | Mike |
| Post-TIA · COIs cohort | 35 contacts (TBD) | — | Wally |
Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.
Three checks for whether Stage 01's Stage Play actually addresses what the prospect is experiencing.
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.
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.
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.
Themselves. Not telling anyone yet. Maybe casually asking a trusted peer if they've heard the name.
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.
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.
| 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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| 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 |
Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.
Three checks for whether Stage 02's execution actually addresses what the prospect is experiencing.
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.
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
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.
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.
Disappearing for six months after the first call. Repeated "are you ready yet?" follow-ups. Pressure tactics. Treating their not-yet as a no.
| 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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| 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 |
Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.
Three checks for whether Stage 03's Stage Play actually addresses what the prospect is experiencing.
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.
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
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.
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.
An inflated valuation they'll later be embarrassed about. Hiding the deal-killers until they surface in diligence. Pretending issues don't exist.
| 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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| Active deal · in-market | Confidential | $26M weighted | Mike |
Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.
Three checks for whether Stage 04's Stage Play actually addresses what the prospect is experiencing.
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.
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
Mike or Wally weekly. Their CFO heavily. A small inner circle. Still not employees.
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.
A CIM that doesn't sound like their business. Boilerplate. Errors. A buyer list that includes companies they'd never sell to.
| 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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| TBD | — | — | — |
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.
Three checks for whether Stage 05's Stage Play actually addresses what the prospect is experiencing.
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.
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
Almost no one. Maybe a partner. The circle of knowledge is the smallest it'll ever be.
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.
Going dark for two weeks. A buyer name surfacing in their network unexpectedly. Sloppiness with the blind teaser. Anything that breaks the confidentiality compact.
| 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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| TBD | — | — | — |
Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.
Three checks for whether Stage 06's Stage Play actually addresses what the prospect is experiencing.
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.
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
Buyers, in carefully managed settings. Mike after every meeting. Spouse and partner about cultural fit. Still not employees.
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.
Letting the highest-price bidder dominate the conversation. Skipping the debrief. Not asking enough about what happens to their team post-close.
| 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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| TBD | — | — | — |
Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.
Three checks for whether Stage 07's Stage Play actually addresses what the prospect is experiencing.
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.
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
Mike, intensively. Their attorney. Their CPA. Spouse, every night.
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.
Walking them through one LOI at a time without comparison. Letting them anchor to the highest headline number. Rushing the exclusivity decision.
| 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 |
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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 |
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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 |
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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.
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In Progress | TBD |
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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.
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In Progress | TBD |
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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.
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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.
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In Progress | Mike leads negotiation · Wally on seller emotional management |
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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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| TBD | — | — | — |
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.
Three checks for whether Stage 08's Stage Play actually addresses what the prospect is experiencing.
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).
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
Three legal teams. A CFO. An accountant. Mike daily. Spouse nightly. Still not employees.
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.
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.
| 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 |
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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 |
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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 |
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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.
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In Progress | Mike runs diligence coordination · Wally manages seller fatigue |
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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.
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In Progress | Mike runs diligence coordination · Wally manages seller fatigue |
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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.
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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.
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In Progress | Mike runs diligence coordination · Wally manages seller fatigue |
| Company | Contact | Note | Rep |
|---|---|---|---|
| TBD | — | — | — |
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.
Three checks for whether Stage 09's Stage Play actually addresses what the prospect is experiencing.
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).
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.
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.
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).
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.
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.
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
Finally, employees. Top customers. Vendors. Their wife or husband, in a way that's now different.
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.
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.
| 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 |
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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 |
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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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| TBD | — | — | — |
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.
Three checks for whether Stage 10's Stage Play actually addresses what the prospect is experiencing.
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.
From entry to exit trigger. The visual to keep in mind before working any deal in this stage.
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.
Peers. Former employees. Industry friends. The network they spent decades building.
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.
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.
| 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 |
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"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 |
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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.
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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.
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In Progress | Wally owns alumni relationship cadence · Mike on industry-specific re-engagement |
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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.
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In Progress | Wally owns alumni relationship cadence · Mike on industry-specific re-engagement |
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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 |
| Company | Contact | Note | Rep |
|---|---|---|---|
| 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 |
Each play feeds this stage with qualified records. Click any play to jump to its audience tab and full play detail.
Three checks for whether Stage 11's Stage Play actually addresses what the prospect is experiencing.
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.
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.
The audience for the Sellers play. Not one population — four tiers, defined below, each with its own cadence.
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.
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 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.
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.
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.
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 |
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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?
From strategy through to running campaigns. Each sub-tab is one step in how a salesperson would actually use this play.
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.
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.
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.
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.
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."
"For any business owner that has never done a sale, you really don't know anything about it. You just don't."
"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."
"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.'"
"Somebody that wasn't going to just try to sell me something, but somebody that actually had lived it and breathed it."
"Having somebody on your team really allowed us to sleep at night. He was looking after our best interests."
"For us, it was all about being able to trust the person representing us. And Mike and Black Belt have the utmost integrity."
"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."
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.
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.
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.
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?
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.
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.
"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.
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.
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.
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.
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.
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.
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.
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.
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 Pipeline | Engaged Early / Engaged Ready |
| TIA Attendees (replied) | Engaged Early |
| TIA Attendees (no reply) | Cold Targeted (still cold) |
| Past Clients | Engaged Not Ready · alumni as advocates |
| Past TIA Shows | Cold Targeted |
| Engaged contacts | Engaged Early |
| LinkedIn network | Cold Targeted |
| Friends & Family | Engaged 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.
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.
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.
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."
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."
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."
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."
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.
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.
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.
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.
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.
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.
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.
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.
How the early conversations are structured. Each artifact below is a Play step in the Pipeline with full ownership and exit criteria.
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?
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.
A working list of channels we know work for Cold Targeted reach. Refined as Mike and Wally report back from the field.
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.
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.
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.
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.
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.
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.
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.
The COIs who aren't currently active referrers but should be on the radar — relationships worth maintaining at low touch for the long game.
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.
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.
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.
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.
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.
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.
| Reply rate · 4-week sequence | Target TBD |
| Conversion Cold Targeted → Engaged Early | Target TBD |
| Fit calls booked / cohort | Target TBD |
| Cycle time · first touch to first reply | ≤ 14 days |
| List exhaustion · % opted-out + % unresponsive after 4 weeks | Target TBD |
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.
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).
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.
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.
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 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Transitions happen on signal, not calendar. HubSpot workflows watch for these signals and reassign lifecycle stage automatically.
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.
CTAs escalate with engagement. The wrong ask at the wrong stage is more damaging than no ask at all.
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 |
|---|---|---|---|---|---|
| ● | ● | ● | ● | Primary across all tiers. Sequenced for Cold Targeted and Engaged Early; manual for Engaged Ready; quarterly for Engaged Not Ready. | |
| ● | ● | ● | · | 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 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.
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.
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.
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.
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.
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."
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."
Last: how we know it's working. Budget, KPIs, and the alumni proof that grounds every claim.
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 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 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.
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.
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.
"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."
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.
The COI play has two parallel outcomes. Both feed the seller play directly.
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).
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.
Build sequencing recommendation: lock down COI play structure within the next 30 days. It's the highest-leverage source of seller pipeline.
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.
Ex-Scopelitis (the largest transportation law firm). Left during COVID when clients were operating entirely on Zoom. Within a month, 300 of his clients followed him to Helmrich Law. Met at Howden night at TIA. Wally on the May 12 call: "He has brought deals to M&A firms that have just shipped the bed, where he's really looking, he was looking to partner with an M&A firm, so this is just, it's perfect." Already referring.
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.
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.
Name note: Cottingham (attorney) is not Cottingham & Butler (insurance broker). Two different organizations. Caught on the May 12 call. Worth disambiguating in HubSpot.
Big insurance broker. Meeting agreed but pushed to June when Mike is back from Italy.
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).
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.
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.
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.
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?"
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.
From strategy through to running campaigns. The COI engine that feeds Sellers, mapped end-to-end.
Now that we know who they are, what they actually said — alumni and active partners in their own words.
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.
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."
"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."
"It was so one-on-one with Black Belt and we felt very comfortable with him and also just in the process."
"I would absolutely advocate that you consider Black Belt. In fact, not even just consider them, just go with them."
"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."
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.
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.
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.
COIs we have identified but never had a real conversation with. Sourced from TIA attendee lists, industry events, profile-match research.
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.
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.
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 |
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.
The journey gives us the when. The narrative below gives us the how — what we say at each tier.
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 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 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?"
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?"
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:
That's the story. Now: how it plays out in an actual COI conversation.
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.
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.
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.
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."
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.
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."
These artifacts live as Play steps across the Pipeline. They're what Wally and Mike use when a COI conversation moves past first interest.
Now: where COIs actually gather, and where partnerships get made.
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.
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.
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.
The plays are the actions. Below: the campaigns and assets running right now to support the COI motion.
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.
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.
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 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.
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).
The pre-show email campaign also surfaced COI candidates before the show even started. Highest-priority follow-ups going into the floor:
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.
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.
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.
The "if we only had time for 5 conversations" list. Walk the floor with intention, not impressions.
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.
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..."
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.
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.
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: 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 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.
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:
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.
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.
Each stage has one ask. Multiple asks per touch is the fastest way to make a busy professional ignore the next email.
Designed to make COIs excited, not reluctant. Year-1 share is deliberately generous. Year-2 keeps relationships warm without creating perpetual obligations.
Paid on every successfully closed deal sourced through the COI's introduction.
Calculated on Next Mile's earned success fee at close.
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-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.
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.
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 |
|---|---|---|---|---|
| ● | ● | ● | Primary across all tiers. Quarterly drip for Targeted, monthly for In Conversation/Engaged. | |
| ● | ● | ● | 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. |
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.
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.
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.
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.
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."
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.
"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.
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.
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.
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.
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.
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.
Buyers don't pay us. The seller does. But cultivating the buyer side produces two outcomes that make the seller play work.
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.
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.
Build sequencing recommendation: Buyers comes after Sellers and COIs. Can largely run on quarterly comparables and deal flow rhythm once content engine is live.
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.
Buyers is the leanest of the three sales plays. Foundational structure is in place; messaging, conversation, and network detail are on the editorial roadmap.
Who they are is clear. What they say about Next Mile — and what they want from a seller relationship — is below.
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.
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.
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.
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.
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.
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.
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.
Their cadence shapes how we speak to them. The narrative is below.
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.
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.
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.
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.
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.
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.
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.
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.
Live artifacts in the Pipeline. Mike runs the intake; structured filters live in the buyer database.
Where buyers actually gather is below.
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.
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.
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.
The plays are scoped. Below: what's currently running on the buyer side — sparse today, by design.
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.
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.
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 |
|---|---|---|---|---|
| ● | ● | ● | 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. |
| ● | ● | · | 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. |
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.
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.
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.
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.
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.
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.
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.
The measurement framework for buyers — the leading indicators that tell us the engine is healthy.
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.
Buyers measured by what they produce upstream — comparables, demand signals, buyer-side validation that makes Seller positioning sharper.
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.
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.
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.
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.
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.
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.
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.
"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."
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.
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.
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.
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.
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.
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.
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).
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
All three are deferred to Phase 3, scoped separately after cutover.
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.
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).
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."
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.
"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."
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).
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).
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.
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.
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.
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.
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.
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.
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).
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.
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.
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.
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 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/
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.
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.
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."
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."
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.
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.
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."
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."
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.
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).
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).
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..."
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.
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).
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.
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).
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.
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.
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).
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.
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.
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.
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.
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).
"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."
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).
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).
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" |
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.
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) |
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.
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.
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.
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
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.
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.
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
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.
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.
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.
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:
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:
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
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.
Facts about the T&L business · persistent, transaction-independent
| Property | Type | Values |
|---|---|---|
| Company Type | Dropdown | Seller, Buyer |
| Asset Type | Dropdown | Asset-Based, Asset-Lite, Non-Asset |
| EBITDA Adj | Number | Currency |
| Annual Revenue | Number | Native field |
Facts about the person · role in the relationship, not the transaction
| Property | Type | Values |
|---|---|---|
| Contact Role | Dropdown | Seller, COI, Buyer, Alumni |
| Lead Status | Dropdown | Native field — reconfigured (see below) |
| COI Category | Dropdown | Insurance, Finance, Legal, Staffing, Data/Compliance, Freight Tech, TMS |
| COI Tier | Dropdown | 1, 2, 3, 4, 5 |
| Referral Count | Number | Integer |
Facts about the transaction · specific to one engagement, can repeat per company
| Property | Type | Values / Notes |
|---|---|---|
| NDA Status | Dropdown | Not Sent, Sent — Awaiting Signature, Signed |
| CIM Status | Dropdown | Not Started, In Review, Approved |
| LOI Signed Date | Date | Triggers Exclusivity Expiry calculation |
| Exclusivity Expiry | Date | Auto-calculated: LOI Signed Date + 60 days |
| Deal Amount | Number | Native field |
| Close Date | Date | Native field |
| Lead Source | Dropdown | Native field |
| Pipeline Stage | Dropdown | Native field — 8 stages |
Pre-deal qualification · lives on contact record
| Status | Description |
|---|---|
| Cold | In the database, never contacted. Sourced from ZoomInfo, LinkedIn, or TIA. No outreach has gone out yet. |
| Contacted | Outreach sent, no reply yet. Wally has made at least one touch — email, call, or LinkedIn. |
| Engagement | Replied or responded. A real conversation has started. Wally is working toward a fit call. |
| Education | Had a fit call, confirmed interest, but timing isn’t right yet. In nurture. Wally checks in quarterly. |
| Pre-Market | Wants to sell but isn’t ready. Actively working with Mike’s portal — sending monthly TMS data, tracking toward a sellable multiple. Long-term hold. |
| Disqualified | Not a fit, opted out, or unresponsive after all touches. Archived. No further outreach. |
Active transactions only · deal created when contact reaches Engagement and fit call confirms readiness
| Stage | Probability | Exit Criteria |
|---|---|---|
| Evaluation | 25% | Engagement agreement signed |
| Preparation | 40% | CIM Status = Approved, buyer list curated |
| Market Engagement | 50% | Qualified buyer confirmed, NDA signed, intro Zoom scheduled |
| Connected | 65% | Multiple IOIs received, field narrowed |
| LOI | 80% | LOI signed, exclusivity executed |
| Diligence | 90% | Wire transferred, PA executed |
| Transition | 100% | 90-day review complete, recommendation letter signed |
Closed Won — Deal complete · contact Contact Role updates to Alumni
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.
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.
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.
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.
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.
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.
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.