Corgi Insurance

Corgi is building an AI financial infrastructure company

About Corgi

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.

About the role

We're standing up a trucking insurance carrier and taking it from zero to $1B in written premium by the end of the year. We need an Account Executive who can close mid-market fleet owners across the country. Auto liability, cargo, per-load. Fleets running 20 to 200 power units are the sweet spot.

You'll work hand-in-hand with an SDR team that keeps your calendar full. Your job is to run discovery, partner with underwriting on the quote, navigate the broker and agent dynamics where they exist, get to bind, and stay close through onboarding, the first claim, and the first renewal.

We work hard, we work long, and we hold each other to a high standard. Hit your numbers consistently and there's a clear path to Enterprise AE.

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. 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.

Your first 30 days

• Close a deal
• Get certified on our product, forms, rates, and appetite so you can hold a real conversation with a fleet owner, dispatcher, or safety director
• Master the fundamentals: loss runs, MCS-90, DOT and FMCSA basics, equipment types, lane and radius analysis
• Build the working rhythm with your SDRs. Sit with them, listen to their dials, sharpen their qualification
• Sit with underwriting, claims, and ops to understand the full quote-to-bind workflow and what we can move on versus what we can't
• Start running discovery calls and getting quotes into market

Your first 60 days

• Hit your first full month of quota
• Build a pipeline that's 3x your monthly quota with clean stages, accurate forecast, and named next steps
• Develop your discovery and quote presentation motion. Find your patterns.
• Surface the win/loss themes back to product, underwriting, and the SDR team so we sharpen the appetite and the targeting
• Build a renewal and expansion playbook for the accounts you've already bound

What you'll do

• Pipeline management. Take qualified meetings from SDRs and work them end to end. Discovery, quote, negotiation, bind. Run a tight CRM, a clean forecast, and an honest pipeline.
• Discovery and underwriting partnership. Pull the loss runs, fleet info, equipment, lanes, drivers, and prior carriers. Partner with underwriters to build a quote that wins and that we can stand behind.
• Closing. Negotiate price, coverage, terms, and effective date. Get the policy bound.
• Account ownership. Stay close through onboarding, the first claim, and the first renewal. Find the expansion (cargo, per-load, additional units, additional entities).
• Cross-functional feedback. Tell product, underwriting, and SDRs what's winning, what's losing, and what we need to change to win more.

What we're looking for

• 3 to 5 years selling B2B, ideally in commercial insurance, trucking, freight, fleet management, or adjacent infrastructure
• You've personally closed deals in the $50k to $500k ACV range and can walk us through how
• Comfortable with technical conversations: coverage forms, rating factors, loss runs, endorsements, MCS-90
• Strong written and verbal communication. You write like an operator, not a brochure
• High agency, high ownership, low drama
• Authorized to work in the US

Bonus

• Prior commercial trucking insurance sales (auto liability, cargo, motor truck cargo, physical damage)
• Existing relationships with mid-market fleets, dispatchers, safety directors, or fleet operations leads
• Experience selling at an insurance carrier, MGA, or trucking-focused brokerage
• Familiarity with DOT and FMCSA filings, MCS-90 endorsements, RRG or captive operations, surplus lines
• Prior producer or commercial lines role at a trucking-focused agency

Compensation

• On-target earnings: $190,000 to $230,000, with competitive base and uncapped commission tied to bound premium
• Equity
• Health, dental, vision

Interview process

1. Screening call
2. Work trial
3. Onsite with the team
4. Decision