The Role

About You

You're excited about eliminating busywork — you love the idea of optimizing workflows, eliminating administrative data entry and making AI do the heavy lifting.
You thrive in fast-moving teams — balancing experimentation with delivery, and pushing AI agents from prototype to production.
You care about UX and understand it deeply — AI tools are only as good as their UX, which you understand deeply and are always seeking for ways to make AI assisted interactions easier.
You'll work closely with leadership — reporting into the CTO/cofounder while collaborating with engineering, data science, and insurance leaders.
You want to build in person with us — this role is based at our San Francisco HQ, where we love solving problems side-by-side.

What You'll Do

Own the AI automation roadmap — from idea to launch: identify opportunities, write PRDs, and partner with engineers and ML teams to deploy agents into production.
Be the voice of "why" — articulate how eliminating data entry unlocks underwriter throughput, faster submissions, and measurable GWP growth.
Keep things moving — prioritize ruthlessly, manage dependencies, and ensure Q4 milestones (e.g. file classification, data structuring, pilot tests) land on time with clear adoption metrics.
Design & Build for scale — your ideas will touch every part of our product. You will build future-proof products that can scale with Shepherd and be leveraged across the business.

You'd be our dream candidate if…
You're a builder at heart — with 3+ years of product management experience in SaaS, AI/ML, or automation-heavy products, skilled at taking complex workflows and making them seamless.
You make things happen — experienced in driving cross-functional initiatives with engineers, ML researchers, and business stakeholders in high-ambiguity environments.
You're a communicator and collaborator — able to translate technical AI trade-offs into clear product decisions, and align diverse teams on outcomes.

Bonus points for experience with AI/ML infrastructure, document parsing or workflow automation, or prior startup/high-growth experience.

A glimpse into our interview process:

Benefits

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

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, or Dallas-Fort Worth Offices Premium office spaces on both coasts with daily lunches provided

Professional Development Access to premium coaching, including leadership development

401(k) Plan Competitive 401(k) plan offered

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