Temporary Human Resources Specialist

Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. We're building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, now we're expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.

We're growing fast, which means our HR operations are getting more complex by the month, more states, more employees, more edge cases. 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.

• Multi-state compliance: tracking state-by-state law changes, drafting policy updates, and making sure they're actually implemented (not just written) across every employee classification and pay range
• 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, not just using AI tools, but rethinking how the function should work
• Growing into ownership of day-to-day HR operations management over time

• Bachelor's degree in any discipline
• At least 2 years of real, hands-on HR generalist experience. You've personally drafted the policy, entered the payroll, handled the compliance filing, not just reviewed someone else's work
• Genuine in-house, multi-state compliance experience
• Comfortable in a small, high-intensity team where you touch payroll, benefits, and compliance yourself

Please note:

Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at addition to base salary, the compensation may include opportunities for equity grants.

• Health coverage
• Dental coverage
• Vision coverage
• Paid time off
• Paid parental leave
• 401(K) plan with employer matching
• Wellness benefits
• Equity opportunities

Part-time, contract, or freelance roles may not be eligible for certain benefits.

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.

Jerry is building the first AI-powered advisor to manage all your physical assets. Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right.

We started with car insurance in 2019, became one of the top 3 brokers in the U.We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.

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.