Corgi Insurance

Corgi is building an AI financial infrastructure company

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
• Comfortable on a cold call within your first week
• Thrives in high-speed, high-accountability roles
• Strong organization and follow-through
• Authorized to work in the US

Bonus, not required:

• Competitive background (athletics, military, debate, sales contests)
• Any prior cold outbound (SDR, door-to-door, fundraising, recruiting)
• Curiosity about trucking, logistics, or insurance

What you'll do

• Make outbound calls and book meetings with fleet owners, dispatchers, safety directors, and platform partners
• Research target accounts before you dial. Know the fleet size, the equipment, the lanes, and the loss history before you pick up the phone
• Keep the CRM updated daily. Activity, notes, next steps, all of it
• Hand qualified meetings to the AE clean, with context the AE can actually use
• Help accounts from deal close through onboarding and first bind
• Clear blockers fast during onboarding
• Spot upsell opportunities and surface them
• Be in-office 5 to 6 days a week on the AE path

Your first week

• Get certified on our product, our appetite, and how trucking insurance actually works so you can hold a real conversation with a fleet owner
• Build your target account list and your call cadence
• Get to 100+ outbound dials and 30+ emails a day
• Book your first qualified meetings for an AE

Why you should join

Ground-floor opportunity. You're joining a new line of business inside a well-funded carrier. Your output shows up in the P&L immediately.

Impact and speed. Fast environment. Direct feedback. Your contributions have immediate effects on the company's success.

Growth potential. Hit your numbers and move up fast: AE, AM, and Ops opportunities. We promote rather than hire whenever we can, and we will likely have many new roles coming in the near future.

Compensation

• $60K to $80K base, determined by experience and performance
• $130K+ OTE
• Health, dental, vision

Interview process

1. Screening call
2. Work trial (live cold calls)
3. Onsite with the team
4. Decision