Introduction
Josh Hollander is joined on this episode of the Insurtech Leadership Podcast by Danil Kolesnikov, founding engineer at Shepherd. Danil was the company's first hire back in 2021, and he has helped build Shepherd from an early stage bet into one of the fastest growing insurtechs in the construction space.
The conversation covers what convinced Danil to join a pre revenue startup, why Shepherd chose to build its own policy admin system instead of buying one off the shelf, and how the company thinks about hiring, culture, and technical debt as it scales. Danil also shares a bold prediction for how AI will reshape mid market underwriting over the next several years.
This is a candid look inside the engineering decisions and leadership lessons behind one of insurtech's most talked about construction MGAs.
Guest Bio
Danil Kolesnikov is the founding engineer at Shepherd, a construction focused MGA that insures general liability, umbrella liability, and workers compensation across the excess and primary markets, and has recently expanded into property with a builders risk offering. Before joining Shepherd as its first hire, Danil worked on experimentation frameworks at Fanatics. He holds a Bachelor of Science from San Jose State University.
Key Topics
Why Danil bet on Shepherd early. Danil explains what drew him to join as Shepherd's first hire, pointing to the strength of the founding team and the lessons he carried over from working with data and experimentation at Fanatics.
The build versus buy decision on policy admin systems. Shepherd evaluated every policy admin system on the market and was unsatisfied, especially given vendors charging two to three percent of the entire premium book. The team decided to build in house instead.
Winner takes best, not winner takes all. Shepherd is selective about which construction risks it insures. Danil explains why that selectivity, combined with how complex and hazardous construction risk is, made a bespoke underwriting platform worth the investment.
Hiring for ambiguity and culture. Danil talks about screening for comfort with ambiguity, the company's Cross the Aisle core value, and why Shepherd's in person, five day a week culture built empathy between engineering and underwriting from day one.
Where AI is actually delivering value in insurance. Danil shares where he has seen AI fall short of the hype, such as replacing OCR for parsing loss runs, and where it genuinely shines, including generative use cases like referral documents.
A bold prediction for underwriting's future. Danil predicts AI will fully underwrite most mid market, five figure premium deals within the next several years, while high touch human relationships remain essential for larger accounts.
Notable Quotes
"We are not in the business of winner takes all. We are in the business of winner takes best."
"The only thing that is constant is people. It's very hard to change the early team, and the early team will shape the next team."
"You can't know exactly where you're going and the exact coordinates, but as long as directionally you're correct, you will be good."
"I would go as far as to say AI will actually replace the underwriter end to end. The broker will call the AI."
Resources
Guest Shepherd: https://www.shepherdinsurance.com Danil Kolesnikov on LinkedIn: https://www.linkedin.com/in/danilkolesnikov/
Host and Organization Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/ Horton International (USA): https://www.horton-usa.com/ Insurtech Leadership Podcast: https://www.linkedin.com/showcase/insurtech-leadership-show
Subscribe and Review
If you enjoyed this episode, subscribe on your favorite platform and leave a review. The Insurtech Leadership Podcast is available on YouTube, Apple Podcasts, and Spotify.