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.
We're standing up a trucking insurance carrier and taking it from zero to $1B in written premium by the end of the year. A big share of that premium will come through embedded partnerships: TMS platforms, ELD providers, load boards, factoring companies, fuel cards, compliance services, and driver qualification platforms that plug Corgi's quote, bind, and COI APIs directly into their products.
We need an Enterprise Account Executive who can land those partnerships. Each one is an eight or nine figure book of business and a multi-stakeholder sale (founder, product, legal, finance, compliance). We need someone who's done that before.
You'll also be the most senior seller in the room. As we hire AEs underneath you, you'll be training the team on trucking insurance, on how to run a partnership cycle, on how to read a loss run and a revenue share term sheet. The directors running this line need someone who can hit quota and develop the people behind them.
We work hard, we work long, and we hold each other to a high standard.
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. 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.
Corgi is building an AI financial infrastructure company
Salary
$100,000 - $180,000
Location
Boston, MA, US
Experience
6+ years
Total raised
$108.0M
Last stage
Series A
Investors
No applications, no recruiter spam. Just the intro.
A few questions to make sure this role is the right shape for you. Two minutes.
I write the intro, send it to the founder, and handle the back-and-forth.
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.