Cloudflare CEO Matthew Prince explains that despite strong revenue growth and cash flow, the company laid off over 20% of its workforce due to structural changes driven by AI.

He argues AI will primarily replace “measurer” roles such as middle management, operations, marketing analytics, and parts of finance, by enabling continuous, highly granular auditing and performance measurement. Cloudflare is reorganizing around fewer managers with more direct reports, more automation in support functions, and a focus on hiring “builders and sellers,” including highly qualified, AI-native interns expected to transition to full-time roles.