John Pullen · Diagnostics for B2B technology CEOs

The number is missing. Or it's hitting and you can't explain how. Either way, your leadership team can't agree on why.

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.

30 min · no pitchor email john@johnpullen.co directly

The pattern

Every leader has a theory. Every theory exonerates the leader telling it. You're tired of running meetings where nobody's wrong while the problem keeps getting worse.

You're probably hearing some version of these:

  • The acquisition was supposed to unlock cross-sell. A year in, the motion still hasn't shown up.
  • Sales is selling things the company can't actually deliver. Or the company is delivering things sales can't sell.
  • The product roadmap and the GTM motion are both real and both serious, and they're moving on different tracks.
  • Revenue is growing and you still can't predict next quarter inside ten percent.
  • There's a lot of commercial activity. You're not sure there's a commercial strategy underneath it.

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.


What this is

A four-week structured diagnostic.

You bring what you're seeing — the symptoms, the friction, the parts of the business that aren't behaving the way they used to. I run a process that surfaces what's actually causing it. You leave with a written diagnostic naming where the problem lives and a plan for how to fix it.

The diagnostic and the working session are my work. Driving what comes next is yours.

This isn't strategy consulting. It isn't a fractional role. It isn't a sales audit. It's the diagnostic that tells you which of those — or which other thing entirely — you actually need.

The problem might be strategy. It might be leadership. It might be sales execution. It might be product. Until you know which, you can't solve it. Most of the expensive mistakes companies make at your stage come from being decisive about the wrong answer.


How the engagement runs
inputs
synthesis
test + deliver
Pre-work
Inputs
Week 1
Symptom map
Week 2
Working diagnostic
Week 3
Pressure test
Week 4
Delivery
60-min kickoff
Document review
Survey deploys
8–10 interviews
Cross-functional, multi-level
Pressure-test mechanisms
Targeted follow-ups
Diagnostic pressure-test session
Plan-to-fix-it session
Written diagnostic
Plan to fix it
Final walkthrough
Delivery
survey runs in parallel
25–50 people · cross-functional
Pre-work

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.

Week 1 — Symptom map

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.

Week 2 — Working 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.

Week 3 — Pressure test

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.

Week 4 — Delivery

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.

After Week 4 (optional)

Most CEOs decide at the end of Week 3 whether to extend with the leadership working session. See the section below.


What you walk away with
A written diagnostic

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.

A plan to fix it

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.

A diagnostic you can use however you want

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.


The optional leadership working session

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.


What this costs

Four-week diagnostic
Companies $30M–$45M in revenue
$40,000
Companies $45M–$60M in revenue
$50,000
Leadership working session
Optional · decide after Week 3
$20,000

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.


Who this is for

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.

Who this isn't for
  • You already know what's wrong and you need execution support. That's a different engagement.
  • You're pre-product-market fit. Nothing has stabilized enough to drift yet. Come back when it has.
  • You want a recommendation that confirms the answer you already have. The point of a real diagnostic is that the answer can surprise you. If you don't want that, this engagement is a waste. (yes, really)
  • You're below $25M. The diagnostic still works at that stage but the price doesn't. The work for you is different.

Why me

Fourteen years operating at the seam where this drift happens — between commercial strategy, product strategy, and operating reality. Most recently leading commercial transformation at Criteo, a public $2B ad tech platform. Before that, running a $100M post-sales P&L through a product pivot at VDX, a PE-backed ad tech company — work that required translating what product was building into what operations could deliver and what commercial could sell. Before that, rebuilding the commercial model at Skai, a PE-backed enterprise software company, from zero to $1M+ enterprise contracts in six months — after diagnosing that the “sales problem” was actually a product-market translation problem.

The pattern across all three: the problem wasn't a function. It was the drift between what the company was building, what it was selling, and how it actually delivered. Your industry knowledge is the input that makes the diagnostic work — what I bring is the pattern recognition for naming where the drift lives. Name it accurately and most of the downstream fixes start working.

If you want to see how I think about this work before booking a call, the LinkedIn series on commercial dysfunction is the entry point, and the Strategic Problem Definition framework is the methodology in long form. Neither is the engagement — they're how I think about the work underneath it.


Next step

A 30-minute call to see if this fits. 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.

30 min · no pitchor email john@johnpullen.co directly