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.
The normal moves don't work because you're solving the wrong problem
You’ve shipped the AI features. You’ve run the strategy sessions. The effort is real. It’s not working because you’re solving a post-PMF problem when you have a pre-PMF problem.
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.
A lens drawn from Carlota Perez
A lens drawn from economic historian Carlota Perez’s work on how technology changes in waves — not all at once. The current information age has already produced five technology systems (personal computers, web, mobile, SaaS/cloud, tech-enabled services); GenAI is the sixth. Each time a new system ascends, companies fit for the prior one find themselves post-PMF in the old system and pre-PMF in the new one simultaneously — which is a recognizable condition, not an unprecedented one.