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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. As the company scales rapidly across multiple states and employee classifications, HR operations are becoming increasingly complex.
This People Operations Generalist role is a hands-on position focused on the judgment-call aspects of HR operations rather than routine processing. You will own multi-state compliance tracking and policy implementation across all employee classifications and pay ranges. You'll lead the annual compliance audit and handbook refresh in your first 90 days, handle escalated payroll and benefits questions, and review work from the Payroll and HR Administration team. A key part of the role is rearchitecting HR operations processes with an AI-native mindset—not just adopting AI tools, but fundamentally rethinking how the function should operate to reduce busywork and focus on high-judgment decisions.
The role reports into a small, high-intensity HR team where you will personally handle compliance filings, policy drafting, and payroll decisions. Over time, you'll grow into broader day-to-day HR operations management. This is ideal for someone who has done hands-on HR generalist work in-house and thrives solving real compliance problems rather than following scripts.
Jerry.ai supports remote work for most roles and also maintains offices in Palo Alto, New York City, Chicago, and Toronto. The company is profitable as of 2024 and consistently ranks among Y Combinator's Top Companies and Forbes/Statista's Best Startup Employers.
REQUIREMENTS:
- Bachelor's degree in any discipline
- Minimum 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
- Comfortable in a small, high-intensity team environment where you touch payroll, benefits, and compliance directly
- Excited (not resistant) to build with AI
NOTE: Jerry.ai can only hire full-time salaried employees currently residing in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada.
