Enterprise Account Executive

About Corgi

Corgi is a full-stack insurance carrier. We're an AI-native company that underwrites and issues 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. 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.

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, appetite, and embedded API so you can speak credibly to any platform's product, legal, or compliance team

Build the target partner list across all categories: TMS and fleet management, dispatch and back-office systems, factoring and freight payment, fuel cards, load boards and freight matching, ELD and telematics, compliance and safety, driver qualification and training

Stand up the partnership playbook: outbound motion, qualification framework, pitch deck, commercial term sheet, and the data room legal will need

Open first conversations with the top 25 partners across categories, with named champions identified at each

Sit with underwriting, product, and engineering to nail down what we can promise on integration timelines, revenue share economics, and SLAs

Your first 60 days

Move the top 10 partners into active commercial diligence

Close the first few partnerships and ship the first embedded integration into market

Build the partner enablement layer: onboarding, certification, revenue reporting, joint marketing, and partner success cadence

Help recruit and onboard the next AE or two underneath you, and start the formal training cadence (weekly deal reviews, ride-alongs, written playbooks)

Feed partner intelligence back to product, underwriting, and engineering so we sharpen the integration and the appetite

What you'll do

Partnership pipeline. Own the partner top of funnel