People Operations Lead ($160K – $210K + Equity) at $60M funded AI-native insurance platform

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

People Operations Lead

Salary

$160K – $210K Equity

Company Description

$60M funded AI-native insurance platform backed by Spark Capital, Y Combinator, and Intact Private Capital

Job Description

You will be the first dedicated People Operations hire, building the entire HR function from scratch for a 75-person startup. This greenfield role involves designing performance frameworks, compensation bands, and manager development programs. You will partner directly with leadership to define the culture and operational infrastructure that supports scaling high-hazard industry insurance through autonomous underwriting.

Location

San Francisco, USA

Why this role is remarkable

• Take true greenfield ownership as the first People Ops lead, designing foundational systems for a high-growth startup that just secured a $42M Series B led by one of the world's largest insurers.
• Direct impact on company culture and organizational design, partnering with executive leadership to scale a team that is pioneering fully agentic, autonomous underwriting technology.
• Exceptional benefits including 100% healthcare coverage, fertility support, unlimited PTO, and professional coaching within a high-performance environment that blends technology and insurance expertise.
  
  

What You Will Do

• Design and implement Shepherd’s first performance management framework, including calibration methodologies, rating rubrics, and the rollout of tools like Lattice.
• Build a comprehensive manager development program from scratch to support first-time and early-career managers through playbooks, training, and feedback loops.
• Partner with Finance and Operations to establish company-wide job leveling frameworks and data-driven compensation bands across a multi-office footprint.
  
  

The ideal candidate

• 7 years of People Operations experience, with a proven track record of building core HR programs from zero to one within high-growth startups (50-200 people).
• Expert-level capability in designing compensation structures, leveling frameworks, and organizational designs while managing day-to-day PEO relationships and payroll.
• A self-starter who excels in ambiguity, possesses exceptional communication skills for sensitive situations, and maintains a high bar for accountability and integrity.
  
  

Who are Jack & Jill?

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.

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.

How does this work?

• 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 it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.
  
  

We never post fake jobs

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.