HR Generalist

Why you should join us:

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. Right now that complexity mostly lands on two people. 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.

The opportunity:

This isn't a role where you're processing paperwork and waiting for direction. You'll own the parts of HR operations that actually require judgment: multi-state compliance, policy drafting, and the payroll and benefits questions that come up when the answer isn't in a handbook. You've done this kind of work before, in-house, hands-on, and you're ready to be t