About the role
About Corgi
Corgi is a full-stack insurance carrier. We're the first AI-native company to underwrite and issue policies while selling direct to the customer. That lets us price risk better and move faster than anyone in the market. We've raised over $108M, and we're launching a new line of business to take the company to its next level.
The $40B+ trucking insurance market is still being underwritten by people with paper files and 1990s rating engines. We're going to fix that.
About the role
We're standing up a trucking insurance carrier and taking it from zero to $1B in written premium by the end of the year. The directors running this line need a Chief of Staff who can sit at the intersection of sales, engineering, and operations and run with whatever the business needs.
We want a seasoned operator or former founder. Someone who's been through a zero-to-one before and can execute against any problem put in front of them. We work hard, we work long, and we hold each other to a high standard.
In year one, expect to help build a division from scratch to $1B in premium: standing up rev ops, owning compliance, assisting operations, hiring and training the team, supporting underwriting, and helping to ship new products and initiatives.
Team
You'll work directly with the two executives leading this division:
Brianna Lynch began her career at EY before leading FP&A and Corporate Development at HarbourVest Partners. She then joined Affiliated Managers Group, a $880 billion asset manager based in MA, where she worked across M&A and Investor Relations acquiring and advising private equity, hedge fund, and venture capital firms. After traveling through Europe and advising startups, she joined Corgi in 2025 as Head of Finance and leading M&A efforts with Drew. Most recently, Brianna and Drew are helping launch the Company’s trucking insurance business and looking to expand their team.
Drew Bregman previously founded a behavioral assessment company that helps the NSA and U.S. military identify talent. Before that, he co-founded Corgi's M&A team, as well as the sales division at Corgi's subsidiary Beagle (40% MoM growth), and earlier built transportation management software as an engineer at a large freight brokerage.
