Chief of Staff, Trucking Insurance

Chief Of Staff For Trucking Insurance Division

Corgi is a full-stack insurance carrier. We are 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. The directors running this line need a Chief Of Staff who can sit at the intersection of sales, engineering, and operations and run with whatever the business needs.

We want a seasoned operator or former founder. Someone who's been through a zero-to-one before and can execute against any problem put in front of them. We work hard, we work long, and we hold each other to a high standard.

In year one, expect to help build a division from scratch to $1B in premium: standing up rev ops, owning compliance, assisting operations, hiring and training the team, supporting underwriting, and helping to ship new products and initiatives.

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, a $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

• Learn the ins and outs of trucking-specific regulatory filings (FMCSA, MCS-90, state DOT, BMC-91X)
• Get the RRG operationally live — claims TPA workflow and bind authority workflow
• Finalize the operational side of broker and aggregator partnerships (commission structures, data feeds, appointment paper)
• Break down our policy forms, endorsements, and rating plans into customer-facing and producer-facing material
• Stand up the systems to track deal flow from quote to bind, and ramp the team on how trucking insurance actually works
• Help the team leads recruit and build the early bench across sales, engineering, and operations

Your First 60 Days

• Stand up and launch our Boston office
• Run the cadence between underwriting, claims, regulatory, sales, engineering, and finance so the division operates as one system instead of six functions
• Coordinate new product launches and the associated rate, rule, and form filings
• Build the weekly metrics pack the executive team and board will use to track the line
• Ship the first round of AI tooling for producers — submission triage, FMCSA pull-and-score, and quote generation — and measure its impact on time-to-bind

What You'll Do

• Cross-functional execution. Sit between sales, underwriting, claims, finance, and product. Unblock people, push decisions to closure, and clean up the loose ends across complex projects.
• Underwriting support. Partner with the underwriting team on workflow, data, and reporting. You won't underwrite, but you'll make sure they can write profitably and quickly.
• Sales operations. Build the sales engine from the ground up: pipeline, CRM, producer onboarding, quote-to-bind workflow, comp plans, territory design, and the reporting that tells us what's working.
• New products and initiatives. Scope, ship, and hand off new products as we scale.
• Operating cadence. Weekly metrics, planning, headcount, division-level reporting up to the executive team and board.
• Hiring. Run requisitions across the division. Sourcing, closing, onboarding, and ramping people fast.

What We're Looking For

• 5+ years operating at a high-growth startup, or you've founded and run something yourself
• You've built sales, operations, or compliance functions from zero.
• You can read a state filing, architect a CRM workflow, and review a comp plan before lunch
• Strong written communication.
• High agency, high ownership

Bonus

• Trucking, commercial auto, or P&C insurance experience
• Familiarity with DOT and FMCSA filings, MCS-90 endorsements, RRG/captive operations, or surplus lines work
• Scaled a division or business unit through hypergrowth
• Prior Chief of Staff, BizOps, or founding-team experience

Compensation

• All-in compensation: $125,000 – $180,000, with base and bonus flexible
• Equity
• Health, dental, vision

Interview Process

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