CW Strategies
Strategy and implementation, from the same person.
I'm Derek Simmons. I build AI-native products and systems for journalism organizations and small businesses — and I've spent 30 years in media learning what actually works.
Most consultants tell you what you should do, then drop the ball in your lap. You still have to find the person who can build it. I'm the other kind: the strategy and the working product come from the same chair. If you've seen something I built and want one of your own, that's the whole pitch.
Shipped
Real products, in the world, working.
PAPJ — papj.org
The platform for the Public Alliance of Professional Journalists: the site, a 13-step credentialing flow, and the Press Box — an AI agent that teaches journalism standards to the public. Designed, built, and operated for a 501(c)(3).
Coach D
A basketball training platform with an AI coach, with paying clients.
Option D
A model-agnostic coaching SDK — one methodology that runs on nine different AI providers with zero dependencies.
lightning/bug
A film made entirely from a terminal. The proof that the production pipeline works end to end.
claudewill.io
A publishing practice built with AI: essays, songs, a film, and the tools behind them, made by one person working with Claude. You're looking at the portfolio piece.
How it works
Fractional, full-service, finished.
Engagements run from a one-time build to a monthly retainer. Strategy, product, and the technical work are one engagement, not three vendors. When I don't have the hands for something, I know the people who do.
The record: 30 years in media — the AP, the Los Angeles Times, and the Star Tribune, where I was its first Chief Creative Officer. Four Pulitzer-winning teams. More than $20 million in documented revenue over eight years (2017–2024). CW Strategies LLC handles the paperwork.