Host Kaylee welcomes Derek Brooks, a Des Moines-based technologist and builder, to discuss his winding career across startups, big tech, campaigns, and fintech. Raised in eastern Iowa, Brooks took an intro web class at Cornell College that sparked everything: he launched hobby websites and even monetized early mobile wallpapers. After college, he joined Pioneer (now Corteva) building software for research scientists, but left for more creative work at Red 5 Interactive and then a remote San Francisco startup in 2010—well before remote work was common.
In 2012, a mentor recruited him to the Obama reelection tech team in Chicago. Brooks helped build integrations that unified disparate campaign data and co-built “Call Tool” to manage high-volume voter outreach without duplicate calls. The pressure was intense, culminating in a nerve-wracking election day at massive scale.
Post-campaign, a well-known tech executive offered to fund teams from the tech org before they even had ideas. Brooks and colleagues spent eight months exploring, landing on “contextual commerce” in 2013—one-tap buy buttons embedded across emails, ads, and apps to streamline mobile checkout. Partnership talks with PayPal evolved into an acquisition about two years in. Inside PayPal, their product struggled for a clear home, so Brooks moved to R&D and later Venmo, relishing the impact of consumer-facing software.
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Feeling slowed by big-company integration work, he took a seven-month sabbatical—golfed (snagged a hole-in-one), tinkered, and contracted (including with Roboflow)—then joined a cybersecurity startup. A former leader from PayPal/Venmo recruited him to Rocket, where Brooks now works on wholesale mortgages, modernizing decades-old systems. He’s energized by Rocket’s mission (“help everyone home”) and its diversity.
Brooks uses AI daily (e.g., Claude Code) to ramp up on languages and speed understanding, viewing AI as a great developer—but not yet an engineer with full-system context. His advice: experiment with AI, ship quick proofs of concept, get in over your head, and change course when work stops being fun. He stays in Iowa for community, cost-of-living advantages, and a supportive startup ecosystem—while indulging hobbies like home automation, carpentry, cars, and camping.