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Jerry.ai is a pre-IPO fintech startup building an AI-powered platform to make car ownership affordable and accessible. The company has raised $240M, achieved 70X revenue growth in 5 years, serves 5M+ customers, and operates across 6 countries with a team of 225. Jerry started with car insurance in 2019 and has since expanded into driving insights, repair marketplace, car diagnostics, and AI-powered chatbots.
You will join as a People Ops Generalist reporting to the Director of HR Operations. This is a hands-on role supporting day-to-day HR operations across the full employee lifecycle. You will own employee onboarding and offboarding, manage HR administration including benefits enrollment and compliance filings (I-9 verification, state new-hire filings), and serve as a first point of contact for employee HR questions.
Key responsibilities include: researching and ensuring compliance with federal, state, and local employment law; drafting and refining HR policies and procedures for leadership review; preparing and maintaining HR documents (offer letters, employment contracts, onboarding materials); managing employee file administration; partnering with hiring managers on role-specific onboarding; supporting employee engagement initiatives (surveys, recognition programs, team-building events); and identifying opportunities to streamline HR processes using AI tools and HRIS platforms.
You will work independently with minimal oversight, handle sensitive HR information with integrity and confidentiality, and collaborate with People Operations Associates and HR Administrators to share knowledge and support their work. The role requires exceptional communication skills, strong attention to detail, and a service-first mindset focused on creating a positive employee experience.
Jerry is remote-first but offers optional in-person or hybrid arrangements at offices in Palo Alto, New York City, Chicago, and Toronto. The company is backed by Y Combinator, led by serial entrepreneurs, and consistently ranks among Y Combinator's Top Companies and Forbes/Statista's Best Startup Employers.
REQUIREMENTS:
- 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 ability to research and apply new requirements
- Experience implementing and building HR automations and systems
- Comfortable working in HRIS platforms
- SHRM-CP or PHR certification preferred
- Must currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada (full-time salaried); or AZ, FL, GA, NV, NY, NC, TN, TX, UT, VA (full-time hourly)
