AI Product Manager

About this role

WHAT WE DO

Yesterday's insurance wasn't built for today's risk. We see it in the data and we feel it in the field. Emerging technology can reinvent how risk is priced and managed, faster and smarter, anchored in proven expertise. First-movers will define the next era of commercial risk management, and Shepherd is building it.

Shepherd is a technology-driven Managing General Underwriter (MGU) transforming commercial Property & Casualty insurance for high-hazard industries. Our mission is to make risk frictionless for the builders and operators shaping the physical world, protecting progress from concept through construction and into decades of operation.

We're building the fastest, smartest commercial risk platform, where underwriting expertise, data, and automation work together to deliver:

- Faster decisions

- Smarter, more accurate pricing

- Better risk outcomes

With Shepherd, safety, speed, and quality no longer trade off against one another. They compound. We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services, where technology, underwriting, and partnerships operate in harmony to support the world's most important industries and the progress they make possible.

OUR INVESTORS

In March 2026, Shepherd raised a $42M Series B https://www.linkedin.com/posts/justindlevine29_today-were-announcing-our-42m-series-b-activity-7442200922291630080-z1gw?rcm=ACoAAAkOMEwBRnAAXmdnQcaOJeioCu6VCqR6Gzc&utm_medium=member_desktop&utm_source=share — bringing total funding to over $60M — led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building. Our investors:

- Intact Private Capital https://www.intactfc.com/about-us/intact-ventures, led our Series B round

- Costanoa Ventures https://costanoa.vc/, led our Series A round

- Spark Capital https://www.sparkcapital.com/, led our Seed round

- Susa Ventures https://www.susaventures.com/, lead our Pre-Seed round

- Y Combinator https://www.ycombinator.com/

- And several others

OUR TEAM

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About https://www.shepherdinsurance.com/about page to learn more.

YOU'LL BE SUPPORTING THE NOVA TEAM

Nova is the team building fully autonomous underwriting. A broker wants coverage for a construction project and emails us a pile of documents: an application, years of claims history, a spreadsheet of what's being built and what it costs, payroll records, prior policies, and a note with the real context buried in the third paragraph. No two brokers send the same thing. An underwriter reads all of it, pulls out a few hundred facts, judges how risky the project is, and prices it. Nova does that work end to end, with agents that read the documents, extract and reconcile the facts, chase down what's missing, and hand back a priced account.

We structure the roadmap as an autonomy ladder borrowed from self-driving. L1 is a human doing the job with assistance. L5 is an email arriving and a priced policy coming out with nobody in between. We're in the middle, and progress means expanding the set of accounts the system handles unsupervised.

The business case is straightforward: our long term vision has a single underwriter overseeing roughly 10x the accounts they handle today, with the system doing intake, analysis, and pricing while the person sets strategy and works exceptions. Getting there is largely a measurement challenge. An account only counts as autonomous if everything on it is right, which makes this a compounding problem rather than an average one, and much of the roadmap comes down to how we define and measure that.

ABOUT THE ROLE

We're looking for an exceptional, entrepreneurial technical product manager to own the roadmap, execution, discovery, and vision for Nova, and to help define what autonomous underwriting looks like for the whole industry.

This is Nova's first product hire. The team is small, extremely high caliber, and growing. The engineers here have taken autonomous underwriting from an idea to real prices on real accounts, making the product calls themselves along the way. You'd be joining people who know this problem cold and who will expect you to get there fast.

This role sits alongside leadership and at the intersection of three domain expertises: engineers who think in eval runs and retrieval quality, underwriters with decades of pricing judgment, and leadership setting the direction of the business. One day you're aligning with our CTO on the autonomy roadmap and pressure-testing the thesis with the leadership team; the next you're pairing with an engineer on a new extraction flow and putting a working version in front of an underwriter before the day ends. Each group holds part of the answer, the best ideas come out of the overlap, and you'll be the person who creates it. If you want to build a category-defining product with real executive air cover and no ceiling on your impact, this is the seat.

The person who does well here is closer to a founder than to a traditional PM. This is an environment for people who need intellectual challenge, thrive in progress, and are motivated by the impact of their work.

WHAT YOU'LL DO

- Own the product end to end. Vision, discovery, prioritization, execution, and the UX and design decisions along the way. Prioritize ruthlessly, be as clear about what we're not building as what we are, and shape how we staff design and engineering against the roadmap. You're accountable for results rather than shipped features: adoption by our underwriters, how much of the work runs without a person, how accurate it is, and whether we can win a deal on a fully autonomous motion.

- Understand the user deeply. Sit with…