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Jerry.ai is a Series C, YC-backed fintech startup with 5M+ customers and $240M in funding, building an AI-powered advisor to manage physical assets (car insurance, home, motorcycle, RV, boat). The company is experiencing rapid growth, which has increased the complexity of HR operations across multiple states and employee classifications.
This HR Generalist role focuses on hands-on, judgment-driven work rather than administrative processing. You will own multi-state compliance tracking and policy implementation, lead the annual compliance audit and handbook refresh (starting in your first 90 days), handle escalated payroll and benefits questions, review and unblock work from the Payroll and HR Administration team, and help rearchitect HR operations with an AI-native mindset. Over time, you'll grow into day-to-day HR operations management.
The role is ideal for someone who has done in-house HR work before and thrives solving real compliance problems, drafting policies, and making judgment calls on complex employee matters. You'll have input on how AI tools are integrated into HR operations, allowing you to spend less time on repetitive tasks and more time on strategic work. You'll work in a small, high-intensity team where you directly handle payroll, benefits, and compliance yourself—not just review others' work.
Jerry is remote-first but has offices in Palo Alto, New York City, Chicago, and Toronto if you prefer hybrid or in-person work. 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
- At least 2 years of hands-on HR generalist experience (you have 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 where you touch payroll, benefits, and compliance yourself
- Excited (not resistant) to build with AI
- Must currently reside in one of these states/provinces: AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada (for full-time salaried); or AZ, FL, GA, NV, NY, NC, TN, TX, UT, VA (for full-time hourly)
