6 March 2026 · 5 min read
Hiring your first AI lead
The most expensive hiring mistake I watch scaleups make is hiring a researcher when they needed an operator.
A research background signals depth on model behaviour. It signals nothing about whether someone can sequence a roadmap, say no to a founder, negotiate with a data protection officer, or ship something small on time.
For a first AI hire in a company under 300 people, weight judgement under ambiguity above everything. Can they tell you which of your use cases should not be built? Can they explain a failure mode to a non-technical board? Have they ever turned something off?
Ask candidates for a system they retired and why. The answers are far more revealing than the ones about systems they launched.
Jess Jeetley advises founders, scaleups and enterprise boards on AI strategy and AI governance. Book a session or take the ISO 42001 course.