derek smart-gordon

Digital Edition · 2026 · Self-Published

Collected
Works

Dev lead. Building AI things at Automattic.

written by
DEREK SMART-GORDON

essays & projects selected works assembled in Portland, Maine
Front Matter

About the Author

a short, mostly accurate biography

I’m a dev lead at Automattic, currently building AI tools for WordPress.com. Before that I spent years on Jetpack. I’ve been working with WordPress for over a decade — long enough to have opinions about it.

I’m a generalist. I’d rather build a rough version of something than read about the right way to do it. Most of what I know came from breaking things and fixing them. Could Be Cool is where a lot of that ends up.


I live in Portland, Maine with my wife Hannah and two cats. We travel a lot — multiple trips a year, wherever looks interesting.

I also have an AI agent named Bella who helped build this site and has stronger opinions about CSS than I do.


github · email

Catalog

Selected Works

projects worth pointing at

Things I'm working on or have worked on.

at automattic

WORK

AI Website Builder

Leading the team building AI-powered site creation for WordPress.com. The thing that might make traditional web design obsolete, or might not.

WORK

Jetpack

Security, performance, and growth tools for millions of WordPress sites. Spent years here before moving to AI.

side projects

EXPERIMENTS

Could Be Cool

Collection of experiments and half-baked ideas. Some finish, most don't. That's the point.

AI

Bella Bot-Gordon

My AI agent. Runs on Claude Opus, lives on a MacBook, has her own website and opinions. She helped build this site.

Reading List

Essays

occasional writing, in reverse chronological