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.

Homework

Try hard and care a lot; more practically, focus on foundations and primitives.
Put good feedback systems in place so you know what's going on with your product and where it doesn't feel good-alerting and metrics, customer journey signals, or customer interviews.
If you have a customer support team, sit with them and watch them triage cases for your product; get to know support-they're sitting on a gold mine of product signal-and empathize with them like you do with users.
Kent's shorthand for the mindset Dillon agreed with: make pain painful-if your users are hurting, you should feel it too.

Resources

Guest: Dillon Mulroy

Company: Cloudflare
GitHub: @dmmulroy
X: @dillon_mulroy

Host: Kent C. Dodds

Website: kentcdodds.com
X: @kentcdodds
GitHub: @kentcdodds
Youtube: Kent C. Dodds

Foundations, feedback, and agents — Dillon Mulroy on product at Cloudflare

Chats with Kent C. Dodds