Jerry makes insurance stress-free | Licensed insurance broker | 100+ top insurers, incl GEICO, Progressive, Allstate | Rated 4.7 in app store, 5+ million users. Backed by Y Combinator.
About the role
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 the person others come to when something's more complicated than usual. Found on 1752vc Careers, the job board for startup and VC roles.
What they're looking for
- Bachelor’s degree in any discipline
- At least 2 years of real, hands-on HR generalist experience. You've personally drafted the policy, entered the payroll, handled the compliance filing, not just reviewed someone else's 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
- While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted
More about this role
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.
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 the person others come to when something's more...
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