Dillon's path runs from internal insurance tools to Vercel Domains to Cloudflare's agent and dashboard work-always with the same through-line: care about the user, get real feedback, and invest in primitives so delighters don't collapse under bad foundations. This episode covers metrics and paging as a product habit, learning from customer escalations, scoping small when AI speeds up coding, and building cross-functional relationships (support, sales, finance) as part of engineering judgment.

You'll hear practical parallels with episodes on delighters and onboarding tension, plus why reviewing agent-written code still matters for system intuition when things break at 2 a.m.

Watch this episode on YouTube