May 22, 2026

Why AI Is Hitting the Middle of the Org Chart First

Cloudflare laid off more than 20% of its workforce despite strong business performance. The reason wasn't financials — it was AI.

Via WSJ

Cloudflare's CEO on why his company laid off 20% of its workforce despite strong performance. His framework is useful: builders, sellers, and measurers. AI is most disruptive to the third group — the internal functions that track, report, audit, and manage. Worth reading if you're thinking about where AI actually changes headcount, and where it doesn't.

Read it at WSJ →


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Twenty years in. Still doing the work.

The best way to reach me is a short note.

By submitting, you agree to our terms of service.