Led the behavioral testing behind California’s new AI assistant, AskCA
I designed the instrument: simulated residents, ordinary and adversarial, questioned AskCA, and AI judges scored every answer against its own instructions. Our method checks that AskCA answers from legitimate government sources and gives residents accurate answers. It’s part of the trust and safety framework ODI built with USDR and Stanford RegLab.
Quoted in Governor Newsom’s AskCA launch, September 2026: “Trust in a tool like this comes from testing it that rigorously, not from hoping it works.” Read the release → Also: ODI, “Lessons from the fire,” Sep 2026 →
Architecting a much loved retailer’s high-volume voice commerce agent
A voice commerce agent, and one of the most complex I’ve worked on. Its callers are loyal and particular, so the conversation has to flex the way a good salesperson does and still feel natural. I scope it, design and prototype the conversations, and build the structured tests that show it behaves before callers meet it.
Built a quoting engine to speed up a specialty insurance agency
Cole is a small agency writing specialized insurance. I built the custom software that does the routine work: a submission comes in, its coverage is checked, it is priced from the agency’s own rates, and the application is filled and queued for a person to approve. AI working for an everyday business.
Launching with the agency soon. I also trained their team to use AI day to day.
Building and shipping Otto, an AI agent for car shoppers
Every question clients pay me to answer — what the assistant says, when it stays quiet, what it will and won’t sell — I answer on my own product first.
Turned a library of tech books into an AI that cites its answers
Senior Director of Product Design · delivered O’Reilly Answers
Rebuilt the product experience as ARR doubled past $200M
Director of Product UX · Arbor design system
Found the performance problem upstream of the AI
Resolution 18% → 33% against a 30% goal
Let people without code build Alexa skills
Alexa Blueprints · active skills up 2000%
Built the UI library that became AWS’s Cloudscape design system
40+ service teams · Cloudscape
Wrote the product vision for Cortana
Bing · Tellme · Cortana
Designed voice systems before most people had talked to one
VP of Design through SpeechCycle’s exit · 1000% higher revenue per project at Intervoice
Field notes on making AI work for real. The first posts are in the works.
Your AI isn’t performing
Diagnostics, strategy, retainers and training, through Redpoint. Starts with a free hour.
You need something built
Agents, internal tools and integrations, scoped in weeks, not quarters.
