A four-week diagnostic for B2B tech CEOs running $30M–$60M companies. Built to tell you what's actually wrong before you spend another quarter on the wrong fix.
Every function sees a different piece of the picture. Each piece is true; none of them add up to the whole. You're tired of meetings where everyone is right about their part and the problem keeps getting worse.
You're probably hearing some version of these:
Different surface symptoms. Usually the same underlying drift: what you're building, what you're selling, and how you actually run the business are no longer one thing. The longer they stay drifted, the more expensive every other fix gets.
Three places commercial dysfunction tends to live. Most companies have soft spots in all three. The question isn't which one is broken — it's which one is currently in the way.
Most CEOs will read these and feel pulled to one. Your team is probably pointing you at one. Both are starting points, not answers.
The work is figuring out which one is actually binding — and why the diagnosis has been pointing somewhere else.
A performance-analytics product the company believed was category-defining. Leadership-level conversations generated enthusiasm and intros to sales. Sales couldn't close any of them. The team called it a sales-execution problem.
The same diagnostic shape I've run inside B2B tech commercial leadership for fifteen years — at $100M, $150M, and $2B.
The work is structured to answer one question: where is the binding constraint on your commercial system, and what needs to change to release it.
A four-week engagement, built for B2B tech CEOs at $30M–$60M companies sitting with a commercial system that isn't producing the results it should.
The implementation stays with you and your senior team. That's the only level at which change like this actually sticks.
Your CRO can tell you what's wrong with sales. Your CPO can tell you what's wrong with product. Neither of them is structurally positioned to tell you whether the problem you're trying to solve is the actual problem — that requires seeing across functions, which their seats don't. That's what an outside diagnostic exists to do.
This is the same diagnostic work I've done from inside commercial leadership roles at B2B tech companies for fifteen years — at $100M, at $150M, at $2B, across bootstrapped, venture-backed, and public contexts. The four-week structure is what's different from the internal version, not the analysis. The compression works because the process exists; the productized engagement is the external version of work I've already run multiple times.
You send me what already exists — board decks, pipeline data, last two QBRs, org chart, recent strategy docs. I read all of it. Sixty-minute kickoff to confirm what you think the problem is and what the leadership team thinks the problem is. Often those two answers are already different. That's information.
Alongside, a short anonymous survey goes out to a cross-section of your organization — 25 to 50 people across functions and levels, sampled to cover the parts of the business where the symptoms are showing up. I can run a finite number of interviews. The survey covers ground the interviews can't reach.
Structured 1:1s with eight to ten people across your organization. Forty-five minutes each. Your leadership team. One level down. And — critically — a cross-section of the people doing the actual work: a few sellers, a few in operations or customer success, a few product managers. Same core questions, different vantage points.
The survey runs in parallel. By end of week, I have the depth and the breadth on the same questions from different vantage points.
The leadership team will tell me what the strategy is. The people doing the work will tell me what actually happens when the strategy meets reality. The gap between those two stories is most of the diagnostic.
I take the symptom map and the survey data together and pressure-test the most likely underlying mechanisms — where product strategy, commercial story, and operating reality have drifted, where they're misaligned by design, and where they're misaligned by neglect. Targeted follow-up interviews with two or three people from the original interview group whose answers raised hypotheses I want to test. By end of week two, I have a working diagnostic.
Two working sessions this week, both 60–90 minutes.
The first is the diagnostic pressure test. I bring you the working diagnostic. Not a presentation — a session designed to either land it or break it. If you break it, the diagnostic was wrong and we rebuild it before going further. If it holds, we move to the second session.
The second is the plan-to-fix-it session. With the diagnostic settled, we work through what to do about it together — so that what gets written in Week 4 reflects your read of the constraints, the politics, and what's actually movable inside your business.
I deliver the written diagnostic and the plan to fix it. Final working session to walk through the plan with you and confirm ownership of the first three moves. I'm available for thirty days after delivery for follow-up questions as you start to execute. After that, you own it.
Most CEOs decide at the end of Week 3 whether to extend with the leadership working session. See below.
Twelve to twenty pages. Names the mechanism, not just the symptoms. Specific enough that your CFO and your CRO read the same document and arrive at the same understanding of the problem. Honest about what's hard to fix and what's structural. Written so it's board-readable as-is — no separate executive summary required.
What to fix, in what order, with what owner, on what timeline. Built around the constraint that you can't do everything at once. Honest about what your existing team can execute and what would require closing a capability gap — and specific about the tradeoffs of the three ways to close it: hire, restructure, or partner.
Take it to the board, use it as the input for a leadership team conversation, or extend the engagement with the leadership working session below.
Most CEOs who buy the diagnostic eventually need a structured way to put it in front of their leadership team. You can run that yourself — some CEOs do, and they do it well. Or you can extend the engagement with a working session I run.
What it is: pre-work conversations with each of your leadership team members (45 minutes each), followed by a single three-hour facilitated working session with the full team, followed by a short written summary of where the team aligned, where it didn't, and the open questions you need to resolve.
What it isn't: a promise that your leadership team will leave aligned. Alignment is your job as the CEO. What I can promise is that the conversation will be more honest, more structured, and more diagnostic-anchored than it would be if you ran it yourself — because I'm the outside party who built the diagnostic and I'm not carrying any of the team's history.
It typically runs in the two weeks after the diagnostic delivers. You decide whether to add it at the end of Week 3 of the core engagement, once you've seen what the diagnostic is shaping up to look like.
Flat fees. The diagnostic work scales with company complexity; the diagnostic price reflects that. The workshop price is flat because the work content is roughly the same across the target range.
Both numbers are sized to be CEO-discretionary. You can make the call inside a week — small enough you don't need to run it past your board, large enough that everyone on your team treats the work seriously once it starts.
These are introductory prices. The product is new and the price will move up as the product matures. If you're one of the first buyers, you get the introductory price and disproportionate attention from me on whether the engagement worked — the first three engagements will reshape this page and the methodology, and the first buyers will see that work directly.
You're a B2B tech CEO. Roughly $30M–$60M in revenue. You're past product-market fit. You're growing — but the curve is flatter than it should be, or your forecast is missing in ways you can't fully explain.
You suspect the problem isn't a single function. You suspect it's something between functions, and you're tired of getting siloed answers from people who only see their part of the picture.
No pitch. We talk about what's going on, I tell you whether this is the right shape of engagement for the problem you're describing, and either we book it or I tell you what would actually help and who's better positioned to do it.