The founding-CEO search, deconstructed

Recruiting a founding CEO into a company that already exists is a strange sell. The candidate is not starting something — they are inheriting a validated thesis, a working v1, and a board that has opinions. The people who thrive in that setup are not always the people who look best in a founder interview.

Source against the wedge, not the sector

We do not look for "a fintech CEO." We look for someone who has personally sold the specific thing the venture needs to sell in its first eighteen months. For Northwind Pay that meant someone who had closed treasury teams at mid-market importers; the sector experience came second.

"We are not hiring for the company the venture becomes. We are hiring for the eighteen months in front of it."

Test with paid work, not case studies

Every shortlisted candidate runs a two-week paid engagement inside the venture before either side commits. They take real customer calls, rewrite the pitch, and present what they would change. It is expensive and it has saved us from two hires that would have taken a year to unwind.

It also flips the power dynamic in a useful way. By the end of the engagement the candidate knows exactly what they are inheriting, which makes the equity conversation an informed one rather than a leap of faith.

Close on ownership and clarity

The two objections that kill offers are always the same: "am I a real founder here?" and "what happens when we disagree with the studio?" We answer both in writing before the offer goes out — founder-level equity, a defined board structure, and an explicit list of the decisions the CEO owns outright.