Founding Engineer, Transportation

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.

• Embedded distribution. Design APIs that integrate Corgi into TMS platforms, ELD providers, load boards, factoring companies, and compliance services, enabling partners to offer quotes, bind coverage, and retrieve insurance documents within their products.

• AI underwriting. Turn FMCSA and DOT data, loss runs, MVRs, and other submission documents into structured information and useful underwriting decisions, with clear controls for human review.

• Partner workflows. Build the portals and tools that brokers, MGAs, and other distribution partners use to submit business, manage quotes, bind policies, and service accounts.

• Transportation data. Build pipelines for telematics, ELD, dashcam, and third-party data that help our underwriting and pricing teams understand risk.

• Production quality. Own reliability, security, observability, and performance. Build systems whose decisions can be understood and whose failures can be diagnosed.

• The engineering team. Help recruit and develop engineers, establish technical standards, and create a culture of fast execution and clear accountability.

What we’re looking for

• Experience shipping consequential software. You have 5+ years building production systems in a high-growth startup or technically demanding environment.

• Ownership from idea through production. You’ve taken an ambiguous problem through product definition, schema design, API contracts, implementation, deployment, and ongoing operation.

• Strong technical judgment. You can make foundational decisions without overengineering, move quickly through reversible choices, and recognize the decisions that deserve more care.

• Comfort across the stack. You can build a React workflow, a Node service, and a Python data pipeline-and follow a problem across those boundaries.

• Practical AI experience. You’ve used LLMs, document extraction, or other AI capabilities in production. You understand evaluations, failure modes, latency, cost, and when a human needs to remain in the loop.

• Product and commercial instinct. You understand how engineering decisions affect conversion, underwriting quality, operating costs, and the experience of the people using your software.

• High agency and clear communication. You identify problems, propose a path forward, and take responsibility for the result. You work directly with users and make tradeoffs explicit.

Bonus

• Prior founding engineer, staff engineer, or technical lead experience
• Experience in insurance, fintech, logistics, or transportation
• Experience building underwriting, pricing, claims, or policy administration systems
• Experience with embedded products and external APIs used by multiple partners
• Familiarity with FMCSA, DOT, telematics, or commercial auto data
• Experience helping recruit and build an engineering team

Compensation and location

• Industry-competitive salary and equity
• Health, dental, and vision benefits
• Based in Boston, in office 5-6 days per week

Interview process

• Screening call
• Technical work trial
• Onsite with the team
• Decision