Account Executive

Corgi Insurance Inc.; San Francisco (CA); On-site; USD 190,000 - 230,000; Full time

Benefits offered by this job

Equity

Health insurance

Dental insurance

Vision insurance

Job summary

Corgi Insurance Inc. in San Francisco is building a trucking insurance carrier and seeks an Account Executive to close mid-market fleet deals nationwide. You will run discovery, partner with underwriting on quotes, navigate broker dynamics, and drive binding through onboarding and renewal.

You will work with an SDR team to fill your calendar, manage a tight CRM, and hit substantial quota. The role offers OTE $190k–$230k with base salary and uncapped commissions, plus equity and benefits.

Qualifications

• 3–5 years of B2B sales, preferably in commercial insurance.
• Experience closing mid-market deals in trucking or fleet sectors.
• Comfortable with technical conversations on coverage forms and rating factors.
• Excellent written and verbal communication; high ownership.
• Authorized to work in the US.

Responsibilities

• Pipeline management from SDR to binding, with accurate forecasting.
• Discovery and underwriting collaboration to build winning quotes.
• Negotiate terms, close the deal, and bind the policy.
• Own accounts through onboarding, first claim, and renewal.
• Provide cross-functional feedback to product, underwriting, and SDRs.

Skills

B2B sales

Commercial insurance

Trucking insurance

Strong communication

Authorized to work in the US

Tools

CRM software

Quote tooling

Job description

# Account ExecutiveBusiness: CorgiDepartment: Sales & MarketingLocation: San Francisco, CAWorkplace: On-siteEmployment: Full-timePay: $90K – $230KExperience: 1+ years**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. 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*** Screening call* Work trial* Onsite with the team* Decision## Apply for This RoleDrag a file here or browsePDF or Word document, up to 4 MB.Work authorizationAre you legally authorized to work in the United States?Visa sponsorshipWill you now or in the future need visa sponsorship to work in the United States?Learn how we handle your information in our privacy notice.