Engineering leadership hiring is getting brutal in the AI era

ivan_bezdomny · x · 2026-07-28

A startup-operator thread says engineering leadership hiring is increasingly broken in the AI era: companies are either asking leaders to rescue a dying org that has already lost its strongest people, or to turn an overvalued AI startup into a real engineering organization. In both cases, the pay is often only comparable to a Google Staff Engineer, while the expected upside is “fix everything.”

The quoted post from Gergely Orosz frames the broader trend: CTO/Head of Engineering/VPE roles at startups and mid-sized companies are getting harder to fill, and even after hiring, these leaders often burn out and leave within months to take a break.

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