Shepherd is building autonomous underwriting for high-hazard commercial insurance. As the first Product Manager for the Nova team, you’ll own the roadmap to transform email submissions into priced policies without human intervention. You will define the “autonomy ladder,” build eval frameworks, and ship agentic workflows alongside a high-caliber engineering team.
AI Product Manager at Shepherd
Shepherd is redefining commercial insurance with autonomous underwriting, and they’re looking for their first AI Product Manager to lead the Nova team. You’ll own the roadmap end-to-end, defining how AI agents read complex documents and price policies for high-hazard industries. This is a high-impact, founder-like role for a technical PM who has shipped production AI and wants to solve deep, structural problems in the physical world. Join a small, elite team in San Francisco and help build the future of financial infrastructure.
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Location
San Francisco, United States
Compensation
$190k-$220k + Equity
Company
Shepherd
Role overview
AI-native commercial insurance
Shepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered. 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.
What you will do
- Own the Nova product end-to-end, defining the vision, discovery, and UX while holding accountability for autonomous accuracy, adoption, and win rates.
- Build and refine the eval framework to serve as the product spec, determining materiality thresholds and measuring model performance across complex document extractions.
- Partner deeply with engineering to prototype agentic flows, write prompts, and analyze failing runs to distinguish between retrieval, model behavior, or data modeling issues.
Who this is a fit for
- Has 4+ years of product management experience with a proven track record of owning hard technical products and shipping production-grade AI systems.
- Possesses deep technical fluency, including the ability to read PRs, write SQL, and reason about model behavior or the statistical distribution of data.
- Demonstrates a founder-like mindset and high agency, comfortable defining product processes from scratch in a fast-paced environment without an inherited playbook.
Why this role is remarkable
- Join as the first PM for Nova, the team building L5 autonomous underwriting, with direct executive air cover and no legacy product playbooks to follow.
- Shepherd is a high-growth Series B startup backed by top-tier investors including Spark Capital and Y Combinator, having raised $67M to date.
- Work at the cutting edge of AI production where accuracy isn’t just a demo—it’s the foundation of pricing risk for the world’s most critical industries.
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.
I recruit from Jack’s network and make the intro when I spot a great match.And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
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What happens next?
Jack’s an AI agent for job searching and career coaching. He works for you.
Jill is the AI recruiter working for the company. She recruits from Jack’s network.
If your profile’s a match and Shepherd wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.