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Jerry.ai is a Series C, YC-backed fintech startup with 5M+ customers and $240M in funding. The company is building an AI-powered advisor to manage physical assets, starting with car insurance and expanding into home, motorcycle, RV, and boat insurance. The company achieved profitability in 2024 and is growing rapidly.
This HR Generalist role is a hands-on position focused on solving real compliance problems and policy work rather than administrative processing. You'll own multi-state HR compliance, policy drafting, payroll and benefits escalations, and lead the annual compliance audit and handbook refresh. You'll also have the opportunity to rearchitect HR operations with an AI-native mindset, reducing repetitive work to focus on judgment-based decisions.
Key responsibilities include:
- Managing multi-state compliance: tracking state-by-state law changes, drafting policy updates, and ensuring implementation across all employee classifications and pay ranges
- Leading the annual compliance audit and handbook refresh in your first 90 days
- Handling escalated payroll, benefits, and leave questions requiring experienced judgment
- Reviewing and unblocking work from the Payroll and HR Administration team
- Rearchitecting HR operations processes with AI-native thinking
- Growing into day-to-day HR operations management over time
The role is fully remote but the company has offices in Palo Alto, New York City, Chicago, and Toronto for those who prefer in-person or hybrid work. Jerry.ai is currently only able to hire full-time salaried employees residing in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada.
REQUIREMENTS:
- Bachelor's degree in any discipline
- At least 2 years of hands-on HR generalist experience (personally drafted policies, entered payroll, handled compliance filings—not just reviewed others' work)
- Genuine in-house, multi-state compliance experience
- Comfort working in a small, high-intensity team where you touch payroll, benefits, and compliance directly
- Excitement (not resistance) about building with AI
