About the role
About Corgi
At Corgi, we're building the first AI-native insurance carrier. We underwrite and issue policies while selling direct to the customer, which lets us price risk better and move faster than anyone in the market. We've raised over $108M and we're launching a trucking insurance carrier from zero.
The $40B+ trucking insurance market is still being underwritten by people with paper files and 1990s rating engines. We're going to fix that, and we need a designer and writer who can get our product, our marketing site, and our customer-facing to the next level.
About the role
This is a hybrid creative role. Half product designer, half marketer, all owner. You'll ship the UI for the workflows our producers and customers actually use, you'll write the blog and the policy explainers, and you'll build the collateral our AEs hand to embedded partners when they walk into a pitch.
You'll be the design and marketing function for this line of business in its first year. That means you don't get to specialize. It also means you get to ship more in one quarter at Corgi than you would in two years anywhere else.
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, an $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.
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. He cares a lot about design and will be in Figma reviewing work with you.
