Founding Engineer, Transportation

About the role

About Corgi

Corgi is building an AI-native insurance carrier. We underwrite and issue our own policies, giving us control over the technology, pricing, and customer experience. We’ve raised over $260M and are building a transportation division spanning trucking, business auto, and future transportation insurance products.

Transportation insurance runs on fragmented systems, manual underwriting, and disconnected data. We’re building the infrastructure to change that: faster decisions, better risk selection, and insurance that fits directly into the platforms transportation businesses already use.

About the role

We’re hiring a Founding Engineer to help build Corgi’s transportation division and own the technology that powers it.

You’ll work directly with the division’s leadership to turn business priorities into products, make foundational architecture decisions, and ship production software. Building on Corgi’s existing carrier infrastructure, you’ll connect distribution, underwriting, pricing, and operations into systems that can support a billion-dollar premium business.

Your scope will include the quote-to-bind pipeline, embedded distribution APIs, AI underwriting tools, partner portals, and the data infrastructure behind risk selection. You’ll decide what to build first, what to reuse, and where the division needs its own capabilities.

This is a hands-on role with substantial technical and product ownership. The systems you build—and the engineers you help recruit—will shape how the division operates as it scales.

Who you’ll work with

You’ll work directly with the two executives leading the division, alongside Corgi’s engineering team:

Brianna Lynch began her career at EY before working in FP&A and Corporate Development at HarbourVest Partners. She later joined Affiliated Managers Group, an $880 billion asset manager, where she worked across M&A and Investor Relations, acquiring and advising private equity, hedge fund, and venture capital firms. She joined Corgi in 2025 as Head of Finance and led M&A efforts alongside Drew. She brings the financial, operational, and underwriting perspective to what we build.

Drew Bregman founded a behavioral assessment company that helps the NSA and U.S. military identify talent. At Corgi, he co-founded the M&A team and helped build the sales division at its subsidiary Beagle, which achieved 40% month-over-month growth. Earlier, he built transportation management software as an engineer at a large freight brokerage. He understands transportation from the software, distribution, and insurance sides—and will be in the code with you when it matters.

What you’ll own

- Technical direction. Define the division’s architecture and engineering priorities, working with Corgi’s core engineering team to build on shared infrastructure and create new capabilities where needed.

- The policy lifecycle. Build the systems that quote, bind, issue, and service trucking and business auto policies, including endorsements, renewals, and cancellations.