Account Executive

Corgi Insurance

Corgi is building an AI financial infrastructure company

Account Executive $90K - $230K • Philadelphia, PA, US Job type Full-time Role Sales Experience 1+ years Visa US citizen/visa only

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About the role

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.

Transportation insurance is still being underwritten by people with paper files and 1990s rating engines. We're going to fix that.

About the role

We're building a national transportation insurance business. We need an Account Executive who can close mid-market fleet owners across the country, and stay close through onboarding, the first claim, and the first renewal.

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 own the relationship from there.

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 transportation 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.

Daniel Hausman, VP, Trucking Program, leads the transportation program this division is building.

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 of transportation insurance: coverage, filings, and fleet operations

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. Work 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, and find the expansion opportunities.

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, transportation, freight, fleet management, or adjacent infrastructure

You've personally closed meaningful deals and can walk us through how

Comfortable with technical conversations across coverage and operations

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 transportation insurance sales experience

Existing relationships with mid-market fleets, dispatchers, safety directors, or fleet operations leads

Experience selling at an insurance carrier, MGA, or transportation-focused brokerage or agency

Compensation

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

Equity

Health, dental, vision

About the interview

Screening call

Work trial

Onsite with the team

Decision

About Corgi Insurance

Corgi is a full-stack insurance carrier building better, faster insurance products for startups. We’re not a broker, so we underwrite and issue policies directly, with fewer handoffs and less friction. Cutting out intermediaries lets us tailor coverage to how companies actually operate and price risk more efficiently.