### Patrick Koeller

### CTO

**Technical co-founder** and proven engineering leader with a track record of scaling startups to successful exits, including building Print Syndicate to $40M in annual revenue and orchestrating ApartmentJet's acquisition by Expedia Group. He has consistently built high-performing engineering teams from inception through scale, led complex technical integrations post-acquisition, and architected enterprise-grade systems for organizations including the Department of Homeland Security. He combines 14+ years of leadership and technical expertise with deep GenAI and cloud infrastructure knowledge to build When's AI-powered platform that transforms complex insurance decisions into seamless digital experiences while ensuring security and scalability.

Stories  
  
Jan 1, 2026  
  
**The Story of When: Two neighbors' mission to fill America's Healthcare Gap.**  
  
  
  
Patrick Koeller](/content/explore/blog/when-founders-story/index.html)

Insight  
  
Apr 7, 2025  
  
**COBRA’s Mid-Life Crisis Hits at 39**  
  
  
  
Patrick Koeller](/content/explore/blog/cobras-mid-life-crisis-hits/index.html)

Insight  
  
Mar 17, 2025  
  
**The True Cost of Offboarding: A Look Beyond the Last Paycheck**  
  
  
  
Patrick Koeller](/content/explore/blog/breaking-down-information-silos-with-the-right-digital-toolkit/index.html)

Insight  
  
Oct 20, 2024  
  
**Picking Insurance Plans with When**  
  
  
  
Patrick Koeller](/content/explore/blog/picking-insurance-plans-with-when/index.html)