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Founding Engineer @ Corgi x Trucking

Business
Trucking
Department
Engineering
Location
Boston, MA · San Francisco, CA
Workplace
On-site
Employment
Full-time
Pay
$125K – $180K
Experience
3+ years

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 & 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
ForbesAs covered in Forbes, May 2025.
The Economic TimesAs covered in The Economic Times, Jul 2025.
Insurance BusinessAs covered in Insurance Business, Jan 2026.
The Wall Street JournalAs covered in The Wall Street Journal, Sep 2025.
Inc.As covered in Inc., Sep 2025.
ForbesAs covered in Forbes, May 2025.
Insurance BusinessAs covered in Insurance Business, Jan 2026.
Inc.As covered in Inc., Sep 2025.
The Economic TimesAs covered in The Economic Times, Jul 2025.
The Wall Street JournalAs covered in The Wall Street Journal, Sep 2025.
Corgi

Coverage may be underwritten by affiliated or partner insurers, including Corgi Insurance Company, Inc., a property and casualty insurance carrier (NAIC #17989).

Certain coverages may be underwritten by risk retention groups, which are state-chartered insurance companies that provide liability coverage to their members pursuant to the Liability Risk Retention Act (15 U.S.C. § 3901 et seq.).

Corgi Insurance Services, Inc. is a licensed insurance producer (CA License #6012791) and acts as program administrator, not as the insurer.

Certain coverages may be available through partner insurers that are admitted in the applicable state and rated A- (Excellent) or better by AM Best. Availability varies by state, line of business, and risk characteristics. Not all coverages are available through every insurer.

Coverage is subject to underwriting approval. Availability varies by jurisdiction, and not all products are available in all states. Limits, retentions, and terms shown on this page are illustrative and may differ from your actual policy. Review your complete policy packet, including declarations, policy forms, endorsements, and accompanying disclosures, for the issuing insurer, coverage terms, conditions, limitations, exclusions, and applicable notices. Your policy documents govern coverage. See our Disclaimers page for full licensing and insurer information.

Securities products and services are offered through ANOS Capital, LLC, a registered broker-dealer and member of FINRA and SIPC, registered with the MSRB, and a subsidiary of Corgi Insurance Services Inc. Corgi Insurance Services Inc. is not a registered broker-dealer or investment adviser. Insurance products are offered through Corgi Insurance Services, Inc. and are not securities.

Corgi ETFs are distributed by Paralel Distributors LLC, which is not affiliated with ANOS Capital. Investing involves risk, including loss of principal. Options involve risk and are not suitable for all investors. For the Options Disclosure Document, contact info@anoscap.com.

Testimonials and customer figures relate to Corgi's insurance services only. Check ANOS Capital on BrokerCheck.