AI Product Manager at Shepherd

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.

• 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.

• 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.

• 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.