People Operations 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.

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 the person others come to when something's more complicated than usual.

You'll also have a real say in how AI fits into HR ops here, spending less time on the repetitive stuff and more time on the judgment calls that need a person.

What You'll Own

Multi-state compliance: tracking state-by-state law changes, drafting policy updates, and making sure they're actually implemented (not just written) across every employee classification and pay range

Our annual compliance audit and handbook refresh, yours to lead start to finish, in your first 90 days

Escalated payroll, benefits, and leave questions that need a more experienced hand

Reviewing and unblocking the work of our Payroll and HR Administration team members

Rearchitecting our HR ops processes with an AI-native mindset, not just using AI tools, but rethinking how the function should work

Growing into ownership of day-to-day HR operations management over time

Who You Are

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.

Please note:

Jerry.ai is only able to hire full‑time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full‑time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by…