SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
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 has grown rapidly since 2019 and is now expanding into new verticals, creating increasing complexity in HR operations that currently lands on two people.
This People Operations Generalist role focuses on hands-on, judgment-driven HR work rather than administrative processing. You will own multi-state compliance tracking and policy updates across all employee classifications and pay ranges, lead the annual compliance audit and handbook refresh 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 processes with an AI-native mindset. Over time, you'll grow into day-to-day HR operations management ownership.
The role is ideal for someone who has done real, hands-on HR generalist work in-house and thrives solving complex compliance problems, drafting policies, and making judgment calls rather than following scripts. You'll have genuine input on how AI tools and processes reshape the function, spending less time on repetitive work and more on high-judgment decisions.
Jerry is remote-first but has offices in Palo Alto, New York City, Chicago, and Toronto for those who prefer in-person or hybrid arrangements. The company is known for strong culture, ranking 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 real, 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 where you touch payroll, benefits, and compliance yourself
- Excited (not resistant) to build with AI
- Must currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada (full-time salaried); or AZ, FL, GA, NV, NY, NC, TN, TX, UT, VA (full-time hourly)
