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:

• 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

About You & the Role

• You love turning data into decisions — you’re excited about transforming pricing into a competitive advantage by integrating new data sources, models, and infrastructure.

• You thrive in fast-moving environments — balancing actuarial, engineering, and underwriting inputs to ship models and tools that make an immediate business impact.

• You’re adaptable and resourceful — when experiments don’t work as planned, you pivot quickly, test new ideas, and keep pushing forward.

• You’ll work closely with leadership — reporting directly into the CTO/cofounder while collaborating with actuarial, underwriting, and engineering leaders across the company.

What You’ll Do

• Own the pricing product roadmap — from idea to launch: write PRDs, define infrastructure needs, and partner with actuaries and engineers to ship models into production.

• Be the voice of “why” — align underwriting, actuarial, and leadership around how new models, data sources, and infrastructure strengthen Shepherd’s growth and capacity story.

• Keep things moving — prioritize ruthlessly, manage cross-functional dependencies, and ensure Q4 pricing milestones land on time (and with measurable impact).

You’d be our dream candidate if…

• You’re a builder at heart — with 4+ years of product management experience in data/ML-heavy or pricing-related products, skilled at working with both technical and business stakeholders.

• You make things happen — experienced in driving data/ML initiatives forward, balancing short-term delivery with long-term scalability, and thriving in fast-moving environments.

• You’re a communicator and collaborator — comfortable translating technical complexity (models, APIs, registries) into clear business impact, and aligning diverse teams around outcomes.

Bonus points for experience in insurance, fintech or other modeling-heavy industries.

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; Ethan, Actuarial Data Scientist

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

Compensation Range: $190K - $220K