Cloudflare CEO Prince lays off more than 20 percent of workforce despite record revenue, saying AI is replacing 'measurers' but not builders or sellers

THE DECODER · May 22, 2026

AI Summary

•Cloudflare cut more than 20 percent of its workforce while posting record revenue and growing at over 30 percent. CEO Matthew Prince says this move—a public company growing fast while cutting staff—has no comparable case in US business history and predicts it will become the norm within a year.
•Prince divides company roles into three categories: builders (product development), sellers (closing deals), and measurers (oversight functions like middle management, internal audit, and compliance). The vast majority of layoffs targeted measurers, whom Prince argues AI can now replace with 'tireless, independent, efficient' precision, while builders and sellers remain safe because engineers become more productive with AI and humans still prefer buying from humans.
•Financial pressures underlie the narrative: Cloudflare's Q1 FY2026 revenue grew 34 percent to $639.8 million but the company posted a $62 million operating loss in the same quarter, with gross margin dropping from 75.9 to 71.2 percent. Headcount surged 40 percent in two years (from 3,682 at end of 2023 to 5,156 at end of 2025), and the company itself acknowledged this rapid growth strained management and operations.

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