More CTOs and engineering leaders are quietly leaving as AI reshapes the job

A wave of CTOs, VPs of engineering, and heads of engineering are leaving senior roles or taking extended career breaks, according to analysis from engineering-leadership writer Gergely Orosz, based on conversations with roughly 20 leaders who recently exited.

The pressure centers on unrealistic AI mandates: founders expecting an overnight shift to "AI-native" engineering while cutting costs 20 to 50 percent and shipping more at the same time. One CTO described managing what they called "AI psychosis" after a founder personally shipped a 60,000-line pull request that left the codebase carrying serious tech debt.

Compensation plays a role too. One CTO's 2 percent equity grant turned out to be worthless once investor preference stacks were factored in, meaning only an exit north of $200 million would return anything to common shareholders. A VP of engineering at another startup described watching leadership chase "a ton of AI stuff" that confused customers and hurt retention, while reliability work on the core product got deprioritized.

Smaller teams compound the pressure. Fullstack engineers paired with AI coding tools are reducing headcount for specialized roles and the management layer above them, narrowing what a leadership job even covers day to day. Orosz's interviews touched leaders with ties to Ramp, Stripe, Notion, Honeycomb, ChatPRD, LaunchDarkly, DoorDash, Anthropic, and Bluesky, alongside Bending Spoons' acquisition of Airtable.

For a small team without a dedicated engineering-leadership layer, the read-through isn't the exodus itself, it's what's driving it: AI-native mandates arriving faster than the org design built to support them.