About
I’m an operator-grade peer to CEOs of post-PMF software companies when the work cuts across more than one seat at the table - when the standard functional moves keep widening the gap rather than closing it. The problem isn’t function-shaped. There’s no seat at the table exactly shaped for it.
Across CEO, CPTO, CPO, and CTO seats over six platform shifts - PC era, web, mobile, SaaS/cloud, tech-enabled services, and now GenAI - I’ve watched the same shape arrive: the company that should be moving but isn’t. The standard moves keep widening the gap. The work needed isn’t a hire and isn’t a turnaround; it’s cross-cutting work that no single function can carry alone.
The work itself: I diagnose the actual shape - rarely a single-seat-shaped gap, even when the surface conversation makes it look that way - then embed alongside the CEO for a bounded window, and transition into the right permanent structure on the other side. The diagnostic pulls the problem out of single-function framing and reads it across multiple layers at once: business model, operating model, product model, human-systems, all pulled through by the customer needs that are under real strain or unmet.
What makes the work hard isn’t only the technical and operational dimension - it’s the human-systems read underneath: what’s actually happening between people in the leadership team, not just what’s on the whiteboard. When I come in alongside the CEO, what changes isn’t only what gets decided, but how the relational architecture of the company reroutes: who decisions go to, who the team looks to for direction, what signals route to whom. Get that read wrong, and the engagement falls apart under stress. Get it right, and you’ve unlocked the next level.
Four exits - Rhithm/Securly, Food on the Table/Scripps, FiveRuns/Workstreamer, Sapling/Macmillan. Work featured in The Lean Startup (Eric Ries) and Running Lean (Ash Maurya).
I’m also building at the substrate level - DXOS, plugin-bramble, regeneration patterns the GenAI shift is making possible. The work keeps my read of what’s next current, beyond any single seat. The engagement work and the substrate work are expressions of the same active inquiry.
Engagements are bounded, mission-defined, with capability transfer on the back end.
If that’s where you are, I’m easy to find.