Job Details

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:

• Y Combinator – W21 cohort
• Susa Ventures – lead our Pre-Seed round
• Spark Capital - lead our Seed round
• Costanoa Ventures + Intact Ventures – lead our Series A round
• And several more.

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 Post-Sales (Servicing) initiative alongside Angelina and Jenny, helping the servicing team automate their workflows and provide a better experience for our partners.

About You

• You get energy from complex, real-world problems — and you're excited to work in industries that impact people's daily lives.
• You thrive in a fast, nimble team — shipping often, moving quickly, and adjusting rituals to whatever gets the job done.
• You're resilient and adaptable — when things don't work as planned, you pivot, experiment, and keep moving forward.
• You'll own the “servicing” journey at Shepherd — digging into the thousand little papercuts that slow customers down and turning them into seamless experiences.
• 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.
• Working closely with leadership — the role will report directly into the Cofounder/CTO, while working closely with leadership across the company

What You'll Do:

• Own the product journey — from idea to launch: gather requirements, shape the vision, write specs, and partner with design/engineering to ship features that matter.
• Be the voice of “why” — align stakeholders across underwriting, ops, and leadership by telling the story, presenting roadmaps, and using data to drive decisions.
• Keep things moving — prioritize ruthlessly, manage the roadmap, remove blockers, and make sure projects land on time (and with impact).

You'd be our dream candidate if…

• You're a builder at heart — with 3+ years of full-stack product management experience (ideally SaaS, fintech, or another regulated space), skilled at breaking down complex problems, using data to make smart calls, and always keeping the customer experience front and center.
• You make things happen — prioritizing across multiple projects, navigating trade-offs, and driving initiatives forward with design, engineering, and business partners in fast-moving, sometimes ambiguous environments.
• You're a communicator and collaborator — able to tell the story behind the “why,” align diverse stakeholders, present ideas with clarity, and turn complex workflows into simple, intuitive solutions.

Bonus points for insurtech/fintech chops, strong technical fluency with engineering teams, or prior startup/high-growth experience.

A glimpse into our interview process:

1. Meet Leslie, recruiting lead
2. Meet Mo, CTO/Cofounder
3. Meet Jenny, Product Lead
4. Meet with Danil and Angelina, Engineering Managers
5. 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