Actual salaries will vary depending on factors including but not limited to location, experience, and performance. The range(s) listed is just one component of Shepherd's total compensation package for employees. Other benefits include stock options, an unlimited paid time off policy, and 100% coverage on medical, vision and dental insurance.

What We Do

We provide savings on insurance premiums for commercial businesses that are leveraging modern technology on their worksites.

While we began with commercial construction, we're expanding into adjacent sectors, including Energy, Agriculture, and Real Estate.

Our Investors

To date, Shepherd has raised over $20M from leading investors, including:

Our Team

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our team page to meet some of us!

The Role

You will be spearheading the AI initiative alongside Avi and Dmitry, advancing AI to Shepherd’s platform and driving industry leading efficiency.

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:

Meet Leslie, recruiting lead
Meet Mo, CTO/Cofounder
Meet Jenny, Product Lead
Meet with Avi and Dmitry, Engineering Leads
Take-home + on-site interviews at our SF HQ

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

Compensation Range: $190K - $220K

Apply now

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