# Jake Dunlap

Jake Dunlap advises companies on revenue operations and go-to-market execution, including sales forecasting, software-stack decisions, AI productivity, and commercial leadership.

- Profile: https://b2binfluencer.marketing/creators/jake-dunlap/
- LinkedIn: https://www.linkedin.com/in/jakedunlap
- LinkedIn followers: 91,553
- YouTube: https://www.youtube.com/channel/UC3iZTOnj-KC1qOBdUmpOagw
- Topics: artificial-intelligence, leadership, sales, revenue-operations, go-to-market-strategy, sales-forecasting
- Based on 11 dated posts, latest 2026-10-05

## Summary

Jake Dunlap is most useful for practical revenue operations and go-to-market execution advice.

- Best for: A mid-market private equity firm or revenue operations engagement with portfolio companies.
- Not for: A consumer packaged-goods brand seeking fixed sponsorship, impressions, or product placement.
- Check first: Confirm audience demographics, engagement, and whether they offer consulting or sponsorship work.

### Takeaways

- A $1.5M forecast miss two days before a board meeting needs buffer.
- Tool sprawl persists because nobody is paid to shrink the stack.
- AI saved time matters when turned into customer conversations, pipeline, or output.

## Main ideas

- **Revenue problems usually trace back to who is paid to fix them**: Dunlap looks past the immediate complaint to ask who benefits from the current arrangement. On tool sprawl, they argue the accumulation is rational: the VP of Sales is measured on hitting the number, marketing on sourced pipeline, customer success on retention, and none of them on cost. Each can request a tool that helps their own metric, so tools pile up. Teams use roughly 30% of what they already own, Dunlap adds, and the gap widens because platforms ship new capability every quarter and no one's job is to find it. Their rule: no new tool gets approved without first answering what it eliminates or what AI replaces. The reason that question goes unasked, they say, is that nobody's compensation depends on the answer. The proposed fix is a standing function rather than an audit, like the shared operator bench: someone owns the problem continuously, not just once. In the AI post, Dunlap says role productivity is the outcome executives push back on hardest.
- **One commercial leader should not carry an entire growth thesis**: Dunlap compares a private equity portfolio's dependence on a single VP of Sales or CRO to customer concentration, a risk no firm would leave untested. The failure is slow and expensive: four to six months to fill the seat, another year before anyone admits the hire is not working, then the same search again — 18 to 24 months of lost growth, landing just when a raise or exit was planned. Dunlap sees a structural, repeatable failure mode in every portfolio company, but treats it as an operating decision rather than a portfolio-level risk. Their proposed hedge is a shared bench of senior go-to-market operators deployed when a gap opens. This is not the Value Creation team, they stress, but hands-on people in the business who provide continuity through each phase of growth. When someone leaves, capacity is reassigned rather than rebuilt from zero.
- **A forecast needs room to be wrong**: Dunlap describes a CRO who learned two days before a board meeting that the quarter would miss by $1.5M, and whose team spent a night rebuilding the forecast from scratch. Their diagnosis is not an unrealistic forecast but a process with no buffer: every number runs in a straight line, with no allowance for a slow week, a product delay, or reps out on leave. Nobody finds out until panic is the only option. Dunlap calls this a design failure, not laziness or deceit, directing the fix away from blame and toward structure. They recommend replacing month-to-month forecasts with a rolling 90-day model and spending at least 20% of the current month fixing the next two, so a team tracking behind plan learns it on day one instead of 48 hours before a board meeting.
- **AI earns its keep through what the saved hours produce**: Dunlap pushes back on the demand that every AI workflow prove an attributable revenue number, noting that no one asked Salesforce to justify itself before replacing Excel or NetSuite before replacing spreadsheets. They tie each workflow to one of six outcomes: pipeline, sales cycle, average selling price, win rate, net revenue retention, and role productivity. Executives readily accept the first five. Role productivity is where the questioning starts, but Dunlap argues the value is real: if an account executive spends eight hours a week on research, CRM updates, call prep, follow-up, and admin, and AI cuts that to three, those five hours have economic value. The company must then answer what it does with the recovered time: more customer conversations, more accounts managed, more pipeline, more deal advancement, or avoiding the headcount growth that would otherwise come with scaling. That, Dunlap argues, is the real opportunity: changing how much output a company gets from each person it employs.

## Work to read

- [PE firms model every risk except the commercial hire](https://www.linkedin.com/posts/jakedunlap_pe-firms-model-every-risk-in-a-portfolio-activity-7510670866167332867-czUB)
- [Tool sprawl persists because nobody is paid to shrink it](https://www.linkedin.com/posts/jakedunlap_youll-never-fix-tool-sprawl-until-someones-activity-7511395100317450240-jruL)
- [A $1.5M miss two days before the board meeting](https://www.linkedin.com/posts/jakedunlap_i-recently-spoke-to-a-cro-who-found-out-his-activity-7511031443633029120-bm2V)
- [Productivity is ROI—if you turn capacity into growth](https://www.linkedin.com/posts/jakedunlap_stop-saying-productivity-gains-arent-real-activity-7511757314425630720-c7BF)

## Partnerships

Jake Dunlap's posts describe client work rather than a published sponsorship or media-partnership programme. Their work includes an ongoing revenue-stack function for clients, a shared bench of senior go-to-market operators that a portfolio can deploy across companies, and AI workflow builds tied to six named outcomes: pipeline, sales cycle, ASP, win rate, NRR, and role productivity. For buyers, this means consulting and operating work scoped around a specific gap, not a fixed sponsorship package. Ask directly about pricing, team composition, reporting expectations, and whether a sponsorship or media partnership is available.

## Alternatives

- Justin Rowe: Choose Rowe over Jake Dunlap when the portfolio company's commercial problem is paid demand generation that looks healthy on paper but is not producing qualified pipeline. Rowe works the measurement gap directly: LinkedIn optimises toward the events it can see, so a program trained on form fills gets good at finding people likely to fill in a form, not people likely to buy. Cost per lead falls while lead quality quietly declines. The fix Rowe describes is sending CRM lifecycle events — MQL, SQL, opportunity, closed won — back to the platform so the algorithm can see the deal. If a portfolio company is spending on LinkedIn and the operating partner cannot answer whether the right accounts are paying attention, that is Rowe's problem, not Dunlap's.
- Hassan Mahmood: Choose Mahmood when the portfolio's commercial pain sits in annual sales planning rather than commercial leadership continuity. Mahmood describes the October-to-Q3 cycle in concrete terms: territories exported from one tool, pipeline pulled from the CRM, a comp file from finance with rep names that do not match either, six weeks of reconciling files by hand, and a plan locked because the team ran out of time rather than because anyone proved it was right. The failure mode — a rep given a number their territory cannot support, a quota gap or capacity shortfall discovered in Q3 — is a planning-model problem. Mahmood's offer is a thinking layer across territory, quota, headcount, comp and forecast, with every number showing its math, sitting on top of platforms like Pigment, Anaplan and Varicent rather than replacing them. That is the right purchase when the operating partner wants scenario answers in an afternoon and traceable assumptions behind each number.
- Matt Green: Choose Green when the portfolio's risk is retention and expansion rather than new-logo leadership. Green's renewal-season argument is specific about who is actually in the room: most champions have defended a budget line about once in their career, while procurement does it every quarter, so vendors are sending someone who went jogging once against a marathon runner. The remedy is a defense kit sent a month before it is needed — the usage story in three sentences a human can say from memory, one defensible peer benchmark or none at all, and pre-written answers to what it costs all in, what breaks if the line is cut, and what the cheaper alternative is — framed with "No ask here." Green's second line of work turns five customer interviews into 90-second stories built from characters, circumstances, conflict, choices and consequences, so reps can answer "I'm not sure my CFO will go for this" with a story rather than a case study. That is the better engagement when net revenue retention is the number the fund is watching.

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AI-assisted summary of public posts. Audience demographics are not available. Engagement appears only where we checked recent posts. Method: https://b2binfluencer.marketing/methodology/