As the first People Operations Lead, you will build Shepherd's people function from scratch during a period of rapid scaling. You'll partner directly with leadership to design and own performance frameworks, compensation bands, and manager development programs. This greenfield role is essential for maintaining our high-performance culture as we expand across multiple national offices.
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People Operations Lead at Withshepherd
Join Withshepherd.com as our first People Operations Lead and build the foundational people infrastructure for a $60M+ venture-backed leader in AI-native insurance. This is a rare greenfield opportunity to design performance frameworks, compensation bands, and manager development programs from scratch. If you have 7+ years of startup experience and want to define how a high-growth AI company treats its people, we want to hear from you.
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Location
San Francisco, United States
Compensation
$160k-$210k + Equity
Company
Shepherd
Role overview
AI-native commercial insurance
Shepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered. Our mission is to make risk frictionless for the builders and operators shaping the physical world — protecting progress from concept through construction and into decades of operation.
What you will do
- Design and implement core people systems including performance management frameworks, job leveling, and compensation bands from the ground up.
- Build and scale a comprehensive manager development program to support and train a growing cohort of first-time and early-career leaders.
- Partner with leadership on strategic org design and headcount planning while managing day-to-day PEO relationships, payroll, and benefits administration.
Who this is a fit for
- 7+ years of HR or People Operations experience, including significant time building programs from zero within a high-growth startup environment.
- Proven expertise in designing performance frameworks and compensation structures using modern tools like Lattice within a PEO-managed environment.
- Strategic builder who thrives in ambiguity, possesses exceptional communication skills, and has a track record of driving complex organizational initiatives with integrity.
Why this role is remarkable
- Greenfield ownership to build the entire People Ops function from zero for a fast-growing, 75-person AI-native startup.
- Work at a $60M+ funded Series B company backed by top-tier investors like Spark Capital, Costanoa Ventures, and Intact Private Capital.
- Direct impact on company culture and organizational design during a critical scaling phase with a multi-office national footprint.
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.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.
I recruit from Jack’s network and make the intro when I spot a great match.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.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
Meet Jack
What happens next?
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 your profile’s a match and Shepherd wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.