Senior Software Engineer, Trucking Insurance

About Corgi

At Corgi, we're building an AI-native insurance carrier. We underwrite and issue policies while selling direct to the customer, which lets us price risk better and move faster than anyone in the market. We've raised over $260M and we're launching a trucking insurance carrier from the ground.

The $40B+ trucking insurance market is still being underwritten by people with paper files and 1990s rating engines. We're going to fix that with engineering.

About the role

The trucking line is being built from scratch on top of Corgi's carrier infrastructure. That means we need a senior engineer who can set technical direction on the systems that actually decide whether we can write $1B in premium this year: the quote-to-bind pipeline, the embedded partnership APIs that plug us into TMS and ELD platforms, the AI underwriting layer that pulls FMCSA data and scores submissions in seconds, and the document workflows that turn loss runs and MVRs into structured data.

You'll own meaningful parts of this stack end to end.

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.

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. He knows the trucking stack from the carrier side, the broker side, and the underwriting side, and will be in the code with you when it matters.

You will

Set direction on the critical systems that quote, bind, issue, and service a trucking policy
Design and build the embedded partnership APIs that plug Corgi into TMS platforms, ELD providers, load boards, factoring companies, and compliance services so quotes and COIs issue inside their products
Build the AI underwriting layer: FMCSA and DOT data ingestion, document extraction from loss runs and MVRs, risk scoring, and the human-in-the-loop tools our underwriters actually live in
Ship the producer and broker portal that handles submissions, quotes, binds, endorsements, and renewals
Build the telematics ingestion pipeline that turns ELD and dashcam data into underwriting signal and lower premiums for safer fleets
Improve the reliability and performance of our internal tooling for underwriters, claims, and operations
Help recruit and ramp the next wave of engineers as we scale the division
Contribute to Corgi's engineering culture as we grow

How to be successful in this role

You have 5+ years building production systems at a high-growth startup or technically demanding environment
You've owned services end to end, including the schema design, the API contract, the deployment, the on-call, and the deprecation
You're comfortable working across the stack. You can ship a React workflow, a Node service, and a Python data pipeline in the same week without asking permission
You've worked with modern AI tooling in production: LLM calls in critical paths, structured extraction from messy documents, RAG systems, evals, the works. You know where the technology helps and where it breaks
You think clearly about tradeoffs and have good product sense. You can tell the difference between a problem worth automating and one worth not solving yet
High agency, high ownership, low drama

Bonus

Prior insurance, insurtech, fintech, or logistics engineering experience
Experience integrating with platform APIs at scale (payments, identity, embedded finance, embedded insurance)
Experience building underwriting, claims, or pricing systems
Familiarity with FMCSA, DOT, telematics, or commercial auto data sources
Prior founding engineer, staff, or technical lead experience

Compensation

Industry competitive salary and equity
Health, dental, vision
In-office in Boston, 5 to 6 days a week. We do not hire for fully remote engineering on this line.

Interview process

Screening call
Technical work trial
Onsite with the team
Decision