Senior Software Engineer, Trucking Insurance
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 $260M and we're launching a trucking insurance carrier from the ground.
The $40B+ trucking insurance market is still being underwritten by people with paper files and 1990s rating engines. We're going to fix that with engineering.
About the role
The trucking line is being built from scratch on top of Corgi's carrier infrastructure. That means we need a senior engineer who can set technical direction on the systems that actually decide whether we can write $1B in premium this year: the quote-to-bind pipeline, the embedded partnership APIs that plug us into TMS and ELD platforms, the AI underwriting layer that pulls FMCSA data and scores submissions in seconds, and the document workflows that turn loss runs and MVRs into structured data.
You'll own meaningful parts of this stack end to end.
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 knows the trucking stack from the carrier side, the broker side, and the underwriting side, and will be in the code with you when it matters.
