People Ops Generalist

You could work anywhere. Why us?

• Join a pre-IPO startup with capital, traction and runway ($240M funded | 70X revenue growth in 5 years | $2T market size)

• Disrupt a massive market and take us to a $10B business in the next few years

• Be immersed in a talent-dense environment and greatly accelerate your career growth

About the opportunity:

We are looking for a hands-on People Ops Generalist to join our dynamic team. Reporting to our Director of HR Operations, you will support day-to-day HR operations - from new employee onboarding and HR administration to compliance and employee support- while helping us build processes that scale as we grow. You’re comfortable operating independently, researching compliance requirements, and drafting policies for leadership review. You have a solid understanding of the employee lifecycle and bring a service-first mindset to every employee interaction.

Jerry.ai is building the first super app to make car ownership affordable and accessible – insurance, buy/sell, registration, loans, safety, repairs, parking, etc – a $2T market in the U.S. We started with insurance in 2019, and since then we’ve launched driving insights, repair marketplace, car diagnostics, and a GenAI-powered chatbot & voicebot. We have amassed over 5M customers, raised $240MM in funding, scaled our revenue 70X and our team to 225 across 6 countries.

How you will make an impact:

• Own the day-to-day administration of the employee lifecycle — onboarding, offboarding, employee file management, and benefits administration

• Partner with hiring managers on role-specific onboarding setup and manage the compliance side of bringing on new hires (I-9 verification, state new-hire filings, benefits enrollment deadlines)

• Research federal, state, and local employment law requirements, monitor our systems and practices for compliance, and help draft and refine policy and procedure changes for leadership review and approval

• Prepare and maintain HR documents, including offer letters, employment contracts, and onboarding materials, ensuring accuracy and compliance

• Serve as a first point of contact for employee questions, providing guidance on HR policies and resolving day-to-day issues independently, escalating complex matters as needed

• Partner with People Operations Associates and HR Administrators, helping answer questions and share knowledge on policies and day-to-day processes

• Support employee engagement initiatives, including surveys, recognition programs, team-building events, and offsites, and help collect feedback to strengthen the employee experience

• Identify opportunities to streamline and document HR processes with an AI-native mindset — using AI tools to speed up research, draft documentation, and reduce manual work

Preferred experience:

• Bachelor’s degree in any discipline

• 2-4 years of hands-on HR generalist experience, ideally at a small or high-growth company where you owned the full employee lifecycle

• Working knowledge of HR compliance and employment law fundamentals, with the ability to research and apply new requirements

• Experience in implementing and building HR automations and systems

• Comfortable working in HRIS platforms

• SHRM-CP or PHR certification preferred

Who you are:

• Comfortable operating independently and taking ownership of day-to-day HR work with minimal oversight

• Exceptional verbal and written communication and interpersonal skills

• Solid judgment and ensures integrity, compliance, and confidentiality when handling highly sensitive information

• Can multitask and prioritize without compromising attention to detail in a fast-paced environment

• Passionate about creating a positive employee experience and isn’t afraid to roll up their sleeves

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 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 [email protected]

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 have been profitable since 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 are a remote-first company, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.