You Can't Automate a Process You Don't Have

In the inaugural episode of Context Window, Kyle Nakatsuji sits 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 100+ clients — from tech-native MGAs to Fortune 500 carriers — CJ reveals the reality of building an AI-native third-party administrator. The conversation centers on a deceptively simple idea: you can't automate a process you don't actually have. Rather than replacing humans, his team uses AI to execute thousands of practical, operational upgrades that are actually transforming insurance claims.

In this episode:

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

Connect with CJ Przybyl on LinkedIn and learn more about Reserv at reserv.com. Listen on Spotify, Apple Podcasts, or watch on YouTube.