Enterprise Account Executive

Enterprise Account Executive

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. 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 across every category we sell into. Outbound, conferences, warm intros, and the inbound that comes from our marketing engine.
• Complex Deal Management. Run multi-month, multi-stakeholder partnership cycles end to end. Founder, product, legal, compliance, finance, all of it. Negotiate revenue share, exclusivity, SLAs, and the technical scope of the integration.
• Cross-Functional Partnership. Work with engineering and product on integration scoping, with underwriting on appetite and pricing, with legal on partner paper, and with finance on revenue share economics.
• Player-Coach. Train the AEs and BDRs who come on after you. Run weekly deal reviews, build the written playbook, ride along on their calls, and develop the next generation of Corgi sellers.
• Renewals and Expansion. Grow the book inside each partnership. Add product lines, deepen integrations, push more volume.
• Market Intelligence. Tell us what's winning, what's losing, and what we need to change to win more partnerships.

What We're Looking For

• 7+ years selling enterprise B2B, with at least 3 of those spent closing platform or embedded partnerships in fintech, insurtech, embedded insurance, or adjacent infrastructure
• You've personally closed seven-figure ACV deals with named platform partners, and you can walk us through how
• You've mentored or formally managed junior sellers, and you can point to people whose careers you helped build
• Comfortable in a technical conversation. You can talk through an API integration scope, a webhook spec, and a revenue share calculation in the same meeting
• Strong written communication. You write like an operator, not a brochure
• High agency, high ownership, low drama

Bonus

• Existing relationships in trucking adjacent platforms: TMS (McLeod, Truckstop, DAT), ELD and telematics (Motive, Samsara, Geotab), factoring and freight payment, fuel cards, load boards, compliance and safety services, driver qualification
• Prior role at an embedded insurance carrier or platform (Cover Genius, bolttech, Branch, Boost, Vouch, At-Bay, Pie, Newfront, Coverwallet)
• Stood up a partnerships function from zero at a launching carrier, MGA, or insurtech
• Familiarity with DOT and FMCSA filings, MCS-90 endorsements, RRG or captive operations, or surplus lines
• Prior Head of Sales, Director of Partnerships, or founding seller experience

Compensation

• On-target earnings: $300,000 to $500,000, with a competitive base and uncapped commission tied to bound premium across your partnerships
• Equity
• Health, dental, vision

Interview Process

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