I work with software company CEOs whose product-market fit isn’t coming together - whether they built something that worked and the ground shifted, or they’re trying to get to fit for the first time. I’ve navigated five technology shifts across 30 years. GenAI is the sixth, not the first.
Engineering, product, executive - three genuinely different disciplines, each in its full depth. Chief architect. VP Product. CPO. CPTO: both at once. CEO. Four exits. Multiple turnarounds. Across companies from scrappy early-stage to acquisition-ready.
Most advisors see one slice - technical, product, or business. Three disciplines in full depth makes it possible to hold all of them simultaneously, without losing resolution when the conversation moves between them.
Sometimes that’s as a thinking partner - privately, on your side of the table, no stake in the answer. Sometimes the situation calls for stepping inside and leading product or engineering directly. The common thread is product-market fit: finding it, losing it, re-finding it.
Your last PMF is now what's in the way
Your last PMF — the pricing model, the architecture, the go-to-market motion — was built from a series of correct choices, each optimized over years. The problem isn’t that you built something broken; it’s that you built something that worked so precisely for the last regime that it’s now the thing in the way. Pre-PMF again doesn’t mean starting over — it means finding where the current PMF ends and the next one begins, while everything you built is still running.
The normal moves don't work because you're solving the wrong problem
You’ve shipped the AI features and run the strategy sessions — the effort is real, but it’s not moving because you’re applying post-PMF solutions to a pre-PMF problem. Post-PMF problems respond to execution; pre-PMF problems require clarity first — what does the market want now, what does the product need to become. Every cycle spent executing instead of finding clarity, GenAI startups gain ground — they’re pre-PMF too, they just started there, and they’re not carrying what you’re carrying.
What losing PMF looks like when you still have it
Product market fit doesn’t announce its departure — the metrics still look right, the team is shipping, the board meeting was fine, and yet privately there’s a feeling that something has subtly shifted. That feeling is a leading indicator; the churn and growth slowdown come later, and by the time they’re visible the departure already happened. AI shifted the ground under something that was working — that’s not failure, it’s the condition, and what you’re feeling is the beginning of being pre-PMF again while the company still looks post-PMF from the outside.