As companies grow from startup to enterprise scale, security programs must evolve dramatically to match increasing risk exposure and operational complexity. This session reveals Cloudflare’s security transformation journey across four growth stages, highlighting the critical pivot points that drove strategic changes — from major VPN attacks that accelerated our zero trust adoption to phishing campaigns that mandated FIDO2 implementation. Learn how we identified security breaking points during rapid scaling, explore the five key principles that guided our evolution, and leave with practical strategies for anticipating and responding to security challenges at each stage.