[Hiring] HR Generalist @Jerry.ai

Role Description

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: tracking state-by-state law changes, drafting policy updates, and making sure they're actually implemented across every employee classification and pay range.
• Our annual compliance audit and handbook refresh, yours to lead start to finish, in your first 90 days.
• Escalated payroll, benefits, and leave questions that need a more experienced hand.
• 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 where you touch payroll, benefits, and compliance yourself.
• Excited (not resistant) to build with AI.

Requirements

• Currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada for full-time salaried positions.
• Currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA for full-time hourly positions.

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 also 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 and big-hearted 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 think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.

We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.

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.