About the role
About Corgi
At Corgi, we're building the first fully automated insurance carrier, and we're hiring early-career sales reps who can sell water to a pond. If you're willing to work harder than you've ever worked before and you want to do sales, in-person, and around the clock, this is your opportunity to join the ground floor of a $100B+ company.
We just 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 you on the phones doing it with us.
We don't care about titles or traditional roles. We just want the best.
This is a ground-floor sales role where you'll learn outbound, talk to fleet owners and dispatchers every day, and move fast. Hit your numbers and you're an AE in 2 to 6 months.
In-office in Boston, 5 to 6 days a week. Not remote. Not hybrid. In the building.
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.
What we're looking for
- Hunger over experience
- Confident communicator
