[Hiring] People Operations Generalist @Jerry.ai

Role Description

We're growing fast, which means our HR operations are getting more complex by the month, more states, more employees, more edge cases. Right now that complexity mostly lands on two people. We need someone who thrives doing the hands-on work: real compliance problems to solve, policies to write, escalations that need judgment instead of a script. You'll also have room to bring AI into how we run HR ops to help cut the busywork so you can spend more time on the parts that matter.

This isn't a role where you're processing paperwork and waiting for direction. You'll own the parts of HR operations that actually require judgment:

• Multi-state compliance, policy drafting, and payroll and benefits questions.
• You'll also have a real say in how AI fits into HR ops.

What you'll own:

• Multi-state compliance: tracking state-by-state law changes, drafting policy updates, and ensuring implementation across every employee classification and pay range.
• Leading our annual compliance audit and handbook refresh in your first 90 days.
• Handling escalated payroll, benefits, and leave questions.
• Reviewing and unblocking the work of our Payroll and HR Administration team members.
• Rearchitecting our HR ops processes with an AI-native mindset.
• Growing into ownership of day-to-day HR operations management over time.

Qualifications

• Bachelor’s degree in any discipline.
• At least 2 years of real, hands-on HR generalist experience.
• Genuine in-house, multi-state compliance experience.
• Comfortable in a small, high-intensity team.
• Excited to build with AI.

Requirements

• Must reside in specified states or Ontario, Canada.

Benefits

• Comprehensive benefits package including health, dental, and vision coverage.
• Paid time off and paid parental leave.
• 401(K) plan with employer matching.
• Wellness benefits.
• Equity opportunities may be part of your total rewards package.

Company Description

Jerry is building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.

Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who care deeply about the quality and impact of our work.

We are a remote-first company, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.