Founding Engineer @ Corgi x Trucking

About Corgi

Insurance is one of the oldest industries in the world and one of the least changed. We're rebuilding it from the inside out. Corgi is an AI-native carrier: we underwrite and issue our own policies and own entire insurance stack end-to-end.

We treat insurance as an engineering problem, because that's what it is. AI isn't a feature we added at the edges; models sit in the critical path of underwriting, document understanding, risk assessment and our entire operations.

Backed to build at scale

Corgi has raised over $260M from leading investors, including TCV, Kindred Ventures, and Y Combinator. We’re well-capitalized to build for the long term and are investing heavily in the technology, talent, and infrastructure needed to redefine insurance.

About the role

We’re building Corgi’s trucking insurance business from scratch, and looking for engineers who want to help redefine how insurance works through technology.

You’ll build the core systems behind the business: quote-to-bind, telematics integrations, ML-powered underwriting, 3rd party data pipelines, document processing, and much more. You’ll work with messy real-world data, solve difficult engineering problems, and build systems where reliability and efficiency matter.

This is an early engineering team, so you’ll have significant ownership. You’ll help shape the architecture, make important technical decisions, and see your work directly impact the business.

What you’ll work on

• Operational systems for quoting, binding, issuing, and servicing trucking policies
• Build scalable, performant APIs
• Build data-heavy pipelines for underwriting models to analyze risk & score risk
• Producer and broker experiences for submissions, quotes, endorsements, and renewals
• Telematics pipelines that turn ELD and dashcam data into valuable signals
• Internal tools for underwriting, claims, and operations

What we’re looking for

• 3–5 years building and shipping production software
• Experience owning systems end-to-end, from data models and APIs through deployment and operations
• Comfortable working across the stack and picking the right tool for the problem
• Experience using modern AI tools in production and an understanding of where they work well — and where they don’t
• Strong product judgment and the ability to turn ambiguous problems into simple, reliable systems
• High ownership, curiosity, and a bias toward shipping

Nice to have, but not required: experience in insurance, fintech, logistics, underwriting, claims, pricing, payments, platform integrations, or telematics.

If you’re early in your career but have built something you’re genuinely proud of, we’d still like to hear from you. We care more about what you’ve built and how you think than the number of years on your resume.

Compensation

• $125K–$180K base, depending on experience
• Up to 30% bonus based on company performance
• Equity
• Health, dental, and vision
• In-office in Boston or San Francisco

Interview Process

• Intro (30 min) — your background, what you've built, and a technical conversation about it
• Technical (1 hr) — implementation, plus a discussion of the choices you made
• System design (1 hr) — how you'd architect a piece of what we're actually building
• AI harness (1 hr) — how you use AI tooling to build a system that ships more than you could by hand