The great PM company stage mismatch

Why great product people fail (and how to fix it)

Ten years ago, a CPO asked me in an interview: “Are you a zero-to-one person or do you love optimizing and growing existing products?” I told them the truth: I was zero-to-one, I’d never worked on anything that wasn’t a new product at that point. I got the offer, but not for the role I wanted. I was adamant he’d made a mistake. He hadn’t. I would’ve been bored within weeks.

That question saved both of us from an expensive mismatch.

That CPO understood something most leaders miss: product talent isn’t fungible. A brilliant PM in the wrong habitat will struggle, get frustrated, and leave. The problem isn’t capability. It’s fit.

If your VP of Product isn’t working out despite being talented and credible, you’re probably facing the same mismatch. Three months ago they seemed perfect. Now you’re wondering if you made a hiring mistake.

You probably didn’t. You hired someone excellent for a different stage than the one you’re actually in.

Here’s the pattern nobody tells you: Product leadership comes in three distinct types, and each one thrives in a specific growth phase. Shreyas Doshi nailed this taxonomy in 2021, showing that most PM hiring and performance failures come from type mismatch, not capability. Hire the wrong type for your stage, and even brilliant people will struggle. Hire the right type, and suddenly product execution clicks.

The three PM archetypes (and where they thrive)

Kent Beck figured this out at Facebook in 2016. Successful teams weren’t following one methodology; they were shapeshifting by stage. He called it 3X:

• Explore (finding product-market fit)

• Expand (scaling what works)

• Extract (optimizing mature business).

Each PM archetype maps to one of these stages.

The Visionary

Lives for zero-to-one. They’re pattern-spotters who see connections others miss. They thrive in ambiguity and get bored with process. In the Explore phase (when you’re still hunting for product-market fit), they’re gold. In Extract phase, when you need predictable execution across 20 product lines, they’re already mentally checked out.

The Craftsperson

Obsesses over taste, UX systems, and product integrity. They’re perfect for the Expand phase, when you’ve found something real and need to turn a rough prototype into something customers love at scale. They’ll fight for quality when everyone else wants to ship faster. Bad fit for early-stage chaos or big-company politics.

The Operator

Sales through people and systems. They excel at portfolio trade-offs and dependable execution. Essential for Extract phase, when you’re running a mature business with predictable playbooks. Lethal to Explore if they arrive too early. I’ve watched one turn a five-person startup into a thirty-meeting-per-week process nightmare within a month.

How to diagnose your actual stage

Most companies lie to themselves about which stage they’re in. The pitch deck says “scale” but the metrics say “still exploring.” Here’s how to tell:

You’re in Explore if:

- Cohort retention curves look like cliffs after month three

- You’re still debating who your real customer is

- Net Revenue Retention (NRR) is below 100% or you haven’t monetized yet

- Most growth is paid, not organic

You’re in Expand if:

- Retention curves flatten by month 3-4

- NRR is above 110% in your target segment

- The product works but support load is crushing you

- You’re bottlenecked by execution, not customer interest

You’re in Extract if:

- The business is predictable enough to hold you accountable to annual plans

- Gross margins are climbing steadily

- Revenue per employee exceeds $200k

- You’re optimizing more than you’re inventing

The costly transition most teams miss

Half your PMs won’t survive stage transitions. That’s not failure. That’s evolution.

The Visionary who found product-market fit becomes the bottleneck preventing scale. The Operator who brought discipline to chaos will stifle the next 0→1 bet. Plan for this.

Real example: Stripe in 2025 runs core payments in Extract mode (reliability, margins, enterprise features) while exploring agentic commerce with OpenAI in pure Explore mode. Different teams. Different scorecards. Different PM types. Same company. Most organizations can’t hold both ideas at once.

What to do when you have the wrong PM for your stage

If you’re in Explore and your PM wants process:

You need to make a change or carve out a parallel track. Every week in the wrong configuration burns cash and morale.

If you’re in Expand and your PM can’t scale through others:

Coach them hard on delegation and systems-building. If they don’t evolve in 90 days, help them find a role that fits.

If you’re in Extract and your PM is bored:

Create a separate Explore track for new bets, or accept they’ll leave. Forcing a Visionary to optimize spreadsheets ends badly for everyone.

The one question that cuts through confusion

Ask yourself: “What failure mode keeps me up at night?”

- “We’ll never find something people desperately want.” You need a Visionary

- “We’ll collapse under our own growth.” You need a Craftsperson

- “We’ll lose discipline and margin.” You need an Operator

Match the PM type to the fear that’s real. Everything else is noise and will end in tears, yours and theirs.

This Ain’t Easy

Most B2B companies never navigate these transitions cleanly. They burn cash in Explore on a product twelve customers kind-of want. They hit Expand and hire their way to chaos. They reach Extract and “innovate” themselves into margin erosion.

The ones that survive change the people and the philosophy on purpose. Know which stage you’re in, not the one you’re pitching to investors. Hire for where you actually are, not where you wish you were.

When great product people fail, it’s almost never about talent. It’s about habitat. Fix the match, and suddenly everyone looks brilliant again.