People Operations Generalist

Jerry; Toronto; Hybrid; CAD 70,000 - 100,000; Full time

Benefits offered by this job

Health, dental & vision coverage

Paid time off

Paid parental leave

401(k) with employer matching

Wellness benefits

Equity opportunities

Job summary

Jerry.ai seeks an experienced HR Operations lead to own multi-state compliance, policy drafting, payroll, and benefits questions. You’ll lead audits and handbook refreshes, support the payroll/HR administration team, and reimagine HR processes with an AI-first approach.

Join a fast-growing, high-intensity team delivering on ambitious compliance and people initiatives. You’ll shape policy, handle complex escalations, and contribute to a flexible, remote-friendly culture that values practical

Qualifications

• Bachelor’s degree required.
• 2+ years of real, hands-on HR generalist experience; you’ve drafted policy, handled payroll, and compliance filing.
• Genuine in-house, multi-state compliance experience.
• Comfortable in a small, high-intensity team handling payroll, benefits, and compliance.

Responsibilities

• Own multi-state compliance, policy updates, and payroll/benefits questions.
• Lead the annual compliance audit and handbook refresh in your first 90 days.
• Unblock payroll, benefits, and leave issues and support payroll/HR administration team.
• Architect HR ops processes with an AI-native mindset.

Skills

HR generalist

Payroll

Policy drafting

Compliance (multi-state)

AI integration

Education

Bachelor's degree

Job description

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.

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 applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at [e-mail]

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.

About Jerry.ai

Jerry is building the first AI-powered advisor to manage all your physical assets. Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey - buying, insuring, maintaining, repairing, selling - is fragmented, complicated, and expensive. Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond. Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay - we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft. We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership. We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.