This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.
She will pick the best candidates from Jack's network.
The next step is to speak to Jack.
Job Title
AI Product Manager
Salary
$190K – $220K + Equity
Company Description
Shepherd is a $67M Series B insurtech backed by Spark Capital, Costanoa Ventures, and Y Combinator that is building autonomous underwriting for high-hazard commercial industries. By combining engineering excellence with deep insurance expertise, Shepherd is creating the risk infrastructure for the next generation of builders and operators shaping the physical world.
Job Description
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.
Location
San Francisco, USA
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.
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.
The ideal candidate
- 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.
Who are Jack & Jill?
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.
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.
How does this work?
- 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 it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.
We never post fake jobs
This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.
Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.
We appreciate this can make them look a bit suspect, but there isn't much we can do about it.
Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.