ยท 4 min read
Case study: a founding CTO replaced without losing an engineer.
One engagement, told in numbers. B2B software, Series A, 28 engineers. Details are shifted enough that the company cannot be recognised; the shape and the orders of magnitude are real.
The starting point
The founding CTO had written the first version of everything and hired the first twenty people. Past 25 engineers the org stalled: no structure survived contact with him, every decision routed through one calendar, and two team leads had quietly left in a year. The board wanted a new CTO. The founder knew it, which made it worse, not better, because everyone was being polite about it.
What the engagement looked like
An 8-month bridge at 3 days a week. The first month was the diagnosis plus the one conversation nobody had dared to have: what role the founder actually wanted. The answer, once the title was off the table, was the architecture, not the org. That reframed the search from a replacement into a completion.
- The founder moved to chief architect with a written scope: the platform's technical direction, no direct reports.
- The org got 3 team leads with real mandates while the seat was held, so the incoming CTO would inherit a structure rather than a queue.
- The search ran alongside: a written profile the board and the founder both signed, 14 candidates, 5 to the panel, 1 hire, signed in month 5, started in month 6.
- Months 6 to 8 were the overlap: the new CTO ran the org while the bridge shrank to a day a week and then to zero.
The numbers
| At the start | At handover, month 8 | |
|---|---|---|
| Engineers | 28 | 29 |
| Regretted departures during the transition | 0 | |
| Team leads with a real mandate | 0 | 3 |
| Time to a signed CTO | 5 months | |
| The founder | CTO, everything routed through him | Chief architect, still in the building |
Why it worked
Because the transition was run as a project with an end state, not as a vigil. An empty or wobbling CTO seat leaks senior engineers within a quarter; what kept them was visible structure and a search that moved. And because the founder conversation happened in week 2 instead of month 6. The most expensive version of this story is the one where everyone stays polite until the best engineers have already decided.
Anonymised by design: sector, sizes and timings are shifted, the structure of what happened is not. References, including for this engagement, on the intro call.
Related: signs your CTO isn't the right CTO for the next stage.