AI Product Manager

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.

In March 2026, Shepherd raised a $42M Series B — 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, led our Series B round

• Costanoa Ventures, led our Series A round

• Spark Capital, led our Seed round

• Susa Ventures, lead our Pre-Seed round

• Y Combinator

• And several others

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.

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.

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.

• 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 underwriters, read submissions yourself, and build the instinct for why one contractor's paperwork is far harder to handle than another's. Find the places where the system can make their work faster, more reliable, and more complete, and turn that into requirements and edge case coverage.

• Own the definition of correct. Our eval framework is effectively the product spec. You'll shape what gets measured, where materiality thresholds sit, which regressions block a release, and how field-level results roll up into claims we're willing to make publicly.

• Set the bar for what autonomous means at Shepherd. How our agents reason, when they act on their own, when they defer, and how they earn an underwriter's trust. Autonomy is only useful if the escalation path is trustworthy, so you'll own how uncertainty gets surfaced and what a person sees when the system hands something back.

• Ship fast with engineering. You'll write prompts, dig through eval data, and pull the failing runs to work out whether a problem is retrieval, model behavior, or how we've modeled the data, all before filing a ticket. Use AI coding agents to prototype, validate, and unblock, and write code yourself when that's the quickest path, without letting the quality bar slip.

• Hungry, with the track record to back it. 4+ years in product, and you've owned the direction of a hard technical product and can point to what came of it. We care about what you've built and how fast you move more than how many years you've been at it.

• Technical in practice. You can read a PR, contribute in an architecture discussion, write your own SQL, and reason about why a model behaves the way it does. You've built things, at work or on your own.

• You've shipped AI into production. You know the difference between a demo and a system people rely on, and you have informed opinions about evals and model quality.

• Statistically literate. You're comfortable reasoning about distributions and thresholds, and you interrogate a metric before you trust it.

• Willing to go deep on the domain. Understanding construction risk well enough to encode it is most of the advantage here. If learning an unfamiliar industry in detail sounds tedious rather than interesting, this won't be a good fit.

• A direct communicator. You write clearly, you disagree in the room, and you don't need a deck to make a decision.

• Opinionated, high agency, experimental. You form a point of view and argue for it. You don't wait to be handed work. Your instinct when something is unclear is to run the experiment rather than debate it. There's no playbook and no product org to lean on here, so you'll define how product works and change it as the team grows.

• Background in autonomy, robotics, or another field where escalation and graduated trust are core concepts

• Document AI, information extraction, or agentic workflow experience

• Time in insurance, fintech, or another regulated industry

• Founder or early-employee experience

• Hands-on with eval tooling and experiment tracking

Shepherd runs on four values. Here's what each one means in this seat.

• Think big, build big. We exist to protect progress and the industries that rely on it. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy.

• Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. As the first PM you set a standard the rest of the team inherits, and the milestones belong to the team rather than to product.

• Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen.

• Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.

🏥 Premium Healthcare
100% contribution to top-tier health, dental, and vision

🥕 Fertility benefits and family building support

🏖️ Unlimited PTO
Flexibility to take the time off, recharge, and perform

🥗 Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

🖥️ SF, NYC, Dallas-Fort Worth, Chicago and LA Offices

📚 Professional Development
Access to premium coaching, including leadership development

🏦 Competitive 401(k) Plan

🐶 Dog-friendly office
Plenty of dogs to play with and make friends with in the SF office