AI Product Manager

What we do

Build the insurance behind the physical world.

The world is building data centers, energy projects, hospitals, schools, and critical infrastructure. Every one of those projects needs insurance to move forward. Yet the process of getting that insurance still depends on scattered documents, manual work, and weeks of back-and-forth.

Shepherd is rebuilding commercial insurance with software, data, AI, and deep underwriting expertise. We started in construction and energy, where understanding the specifics of a project matters and better decisions have consequences far beyond a screen.

We develop insurance products, decide which risks to insure and how to price them, and partner with established insurers to back the coverage. We own the platform our team uses to turn complex submissions into coverage for the builders and operators shaping the world around us.

Real problems. Real ownership.

Our engineers, designers, underwriters, CX, and actuaries build together. The problems span turning messy documents into reliable data, making pricing more precise, and designing AI agents that can take on increasingly complex underwriting work.

The ambition is a platform where experts spend more time on judgment and relationships, supported by software that handles the work around them. Join us to build systems whose decisions help real projects get built.

630+ customers / $500B+ insured project value

Our investors

Capital to build. Partners to grow with.

$67M total funding / $42M Series B in March 2026

Shepherd is backed by Intact Private Capital, Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator. In March 2026, we announced a $42M Series B led by Intact Private Capital, bringing our total funding to $67M.

Intact is also a capacity partner. Alongside its investment, Intact works with Shepherd to bring insurance products to market. That relationship connects our platform and underwriting expertise with the resources of a global insurer.

A bigger opportunity ahead

We are investing in new insurance products, our underwriting team, and the path toward autonomous underwriting. For the people joining Shepherd, that means the chance to shape both the technology and the business it makes possible.

Our backing brings together investors who build technology companies and partners who understand insurance. We are building a company that earns the confidence of both.

About the Role

As a Product Manager, you’ll build products that continue to make Shepherd the leader in the agentic underwriting space. You’ll be a thought leader on how to adopt the latest AI advancements into our product and transform the way our users work. We're looking for an exceptional, entrepreneurial product manager to own roadmap, execution, discovery, and vision.

This role sits 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.

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 underwriter sets portfolio strategy and handles agent escalations.

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

• Rethink the work, not just speed it up. Understand underwriting deeply enough to see which parts of the job should change entirely, not just get faster. Turn that into bets, requirements, and edge-case coverage.

• Build for adoption. Turn proven bets into platform capabilities other EPD teams build on. Decide when a prototype is ready to graduate, what the interface looks like for internal teams, and how you know adoption is working.

• 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 how AI is part of the product at Shepherd. Decide when and how we adopt new model capabilities as they emerge. How our agents reason, when they act on their own, when they defer, and how they earn a user’s trust.

• Ship fast with engineering. Use AI to prototype, validate, and unblock, and write code yourself when that's the quickest path, without letting the quality bar slip.

Who you are

• 4+ years in product, including owning the direction of hard technical products. You 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.

• Resourceful, opinionated, high agency, experimental. You are comfortable with ambiguity, can go chase down answers or learn more when needed. 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.

• A bar raiser. You find ways to go above and beyond, and make your teams better as a result.

• 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.

• Willing to go deep on the domain. Understanding insurance risk and user workflows deeply.

• A direct communicator. You write clearly, you disagree in the room, and you have insights and product intuition to back up your ideas.

Nice to have

• Experience in document AI, information extraction, or agentic workflow

• Background in insurance, fintech, or another regulated industry

• Founder or early-employee experience

• Hands-on with eval tooling and experiment tracking

How we work

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. Come set a standard the rest of the team inherits.

• 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.

Benefits 

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

🥕 Fertility benefits and family building support

🏖️ Flexible 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