Derek Featherstone

Accessibility × AI Strategist & Builder

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From the inside.

I write about accessibility and inclusive design from inside the work, while it's happening. Most days that means the lab, testing what AI actually does and doesn't do for accessibility: over 5,000 AI-generated modals graded so far, every new model run through the modal test. The results land here first, before they're public — along with what never makes the write-up: what surprised me, what broke, what I'm still chewing on.

If you design, this letter is for the version of you that wants to be genuinely good at this — the kind of good that changes what you do on Monday, not just what you can cite. If you lead — a design team, a design system, an accessibility practice — it's for making the work stick past your own reach; a lot of what I write gets forwarded to teams, and that's by design.

I've been at this 27 years: founded Simply Accessible, led product accessibility across 130+ products at Salesforce, and I'm still in it every day. I don't write about anything I haven't done.

Read a few before you decide

  • I made AI build the same modal 2,340 times. Here's what I learned.
  • When roles collapse, so does judgement.
  • What I learned from office hours conversations

Replies steer the work — tell me what to test next, and I'll probably test it. When I have something worth sending, I send it. I'll also tell you when I'm running a new course, workshop, or cohort. If it's not for you, unsubscribe any time.

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Inclusive, by design.

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© 2026 Derek Featherstone