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.
How Founders Move Past Their Carrying Limit
The tangle here is in post-PMF software companies (post-fit through Series B, or service companies) where the founders are the right people, but the leadership capacity to reach the next stage outruns what they can carry alone. The usual moves - hiring a level too low, the founder absorbing more, a fractional CXO who never fully lands - haven’t closed the gap. The work: I diagnose the actual shape (sometimes a single founder needing an operator-grade peer alongside, sometimes co-founder dynamics needing a rebalance), then embed for a bounded window, and then transition the company into the right permanent structure. I’ve taken two engagements with this pattern through to acquisition exits with the founder team staying.
The Incumbent's Unexpected Unfair Advantage
The tangle here is in post-PMF software companies (post-fit through Series B) where the founders are the right people, but the leadership capacity to reach the next stage outruns what they can carry alone. The usual moves - hiring a level too low, the founder absorbing more, a fractional CXO who never fully lands - haven’t closed the gap. The work: I diagnose the actual shape (sometimes a single founder needing an operator-grade peer alongside, sometimes co-founder dynamics needing a rebalance), then embed for a bounded window, and then transition the company into the right permanent structure. I’ve taken two engagements with this pattern through to acquisition exits with the founder team staying.
The Incumbent's Unexpected Unfair Advantage
The tangle here is in post-PMF software companies (post-fit through Series B) where the founders are the right people, but the leadership capacity to reach the next stage outruns what they can carry alone. The usual moves - hiring a level too low, the founder absorbing more, a fractional CXO who never fully lands - haven’t closed the gap. The work: I diagnose the actual shape (sometimes a single founder needing an operator-grade peer alongside, sometimes co-founder dynamics needing a rebalance), then embed for a bounded window, and then transition the company into the right permanent structure. I’ve taken two engagements with this pattern through to acquisition exits with the founder team staying.