You Can’t Automate a Process You Don’t Have | CJ Przybyl, Co-Founder and CEO of Reserv

In the inaugural episode of "Context Window: AI, Insurance & The Humans Behind It,” we sit down with CJ Przybyl, co-founder and CEO of Reserv and adjunct professor at UChicago Booth, to cut through the generative AI hype.

As a second-time Insurtech founder who has rapidly scaled Reserv to serve over 100+ clients, from tech-native MGAs to Fortune 500 carriers, CJ reveals the reality of building an AI-native third-party administrator.

Discover why replacing humans was never the goal, and how his team is using AI to execute thousands of practical, operational upgrades that are actually transforming the insurance claims industry.

00:00 - The Cold Open: You Can't Automate What You Don't Have

01:40 - CJ’s Origin Story: From Motorola Flip Phones to Insurtech

18:50 - The Reality of Entrepreneurship vs. Investment Banking

26:20 - Catching the Car: Onboarding 90 People in 60 Days

41:20 - Lead Bullets vs. Silver Bullets: What Works in the Insurance Business

47:00 - The Strict ROI Trap Holding Legacy Carriers Back

54:10 - The Real AI Disruption: Infrastructure vs. Operations

CJ Przybyl is the Co-Founder and CEO of Reserv, an AI-powered third-party administrator redefining the property and casualty insurance claims industry.

A pioneer and second-time founder in the Insurtech space, CJ leads his team in leveraging human-centered technology and AI orchestration at scale to transform claims handling into a smarter, faster, and more transparent process.

Beyond Reserv, he serves as an adjunct professor of entrepreneurship at the University of Chicago Booth School of Business.

Subscribe to Context Window for more insights from the operators deploying AI inside real insurance companies.

Connect with Kyle Nakatsuji on LinkedIn: https://www.linkedin.com/in/kylenakatsuji/ 

Connect with CJ Przybyl on LinkedIn: https://www.linkedin.com/in/cj-przybyl-9061383/ 

Learn more about Reserv: https://www.reserv.com/

See what Dearborn Labs is building: We don’t just talk about AI in insurance, we build the technology that powers it. Explore our latest projects and partnerships at https://dearbornlabs.com/