Senior People Operations Manager at Jerry.ai in Palo Alto, CA

YOU COULD WORK ANYWHERE. WHY US? - Join a pre-IPO startup with capital, traction and runway ($240M funded | 40X revenue growth in 4 years | $2T market size) - Work closely with brilliant leaders and team mates from companies like Nvidia, Better, McKinsey, etc. - Disrupt a massive market and take us to a $5B business in the next few years - Be immersed in a talent-dense environment and greatly accelerate your career growth ABOUT THE OPPORTUNITY: We are hiring a Senior People Operations Manager to lead the operational foundation of our People function. This role will own the day-to-day and strategic execution of payroll, benefits, HR compliance, employment taxes, HR systems, immigration coordination, and global workforce operations (including EOR management). This role will also manage a distributed People Operations support team (two Philippines-based associates) responsible for daily execution and employee support workflows. You will set priorities, ensure operational rigor, and raise the bar on accuracy, documentation, and service delivery as the company scales. This position partners closely with our HRBP lead, who will focus on employee relations, performance management, talent density, and leadership support—while you ensure the systems and operations behind the employee experience are consistent, compliant, and scalable. This position can be fully remote from AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NY, NV, OR, TN, TX, UT, VA, or Ontario, Canada, or onsite/hybrid from Palo Alto, New York, or Toronto. KEY RESPONSIBILITIES: PEOPLE OPERATIONS & TEAM LEADERSHIP: - Team Management: Lead a distributed offshore People Ops team; provide coaching and structure to two direct reports. - Service Delivery: Establish workflows, quality standards, and SLAs for onboarding, payroll, and benefits. - Process Excellence: Drive HRIS data integrity, automation, and self-service to reduce manual work and scale operations. Building and utilizing AI tools to automate and optimize HR processes. PAYROLL, BENEFITS & FINANCE: - Payroll Ownership: Oversee end-to-end payroll processing, tax withholding, and year-end reporting (W-2s) for all populations. - Benefits Strategy: Lead open enrollment and manage the full suite of health and retirement programs, vendor performance, and broker relations. - Global Operations: Manage EOR partnerships for international employees, including contract updates and cost forecasting with Finance. COMPLIANCE, RISK & LIFECYCLE: - Regulatory Oversight: Own the compliance calendar (federal, state, local) and lead audits for payroll and documentation. - Employee Lifecycle: Oversee onboarding/offboarding execution and streamline operational handoffs with IT and Legal. - Mobility: Coordinate with counsel to manage immigration filings, visa tracking, and work authorization support. WHAT SUCCESS LOOKS LIKE: - Payroll and benefits run smoothly, with minimal escalations and high employee trust. - Compliance processes are proactive, organized, and audit-ready at all times. - EOR and immigration workflows are predictable, well-managed, and low-risk. - Associates are well-supported and operating with clarity, accountability, and strong quality standards. - People Ops runs as a scalable service function—fast, accurate, and consistent. QUALIFICATIONS: - 7+ years of progressive People Operations experience, including payroll, benefits, and compliance ownership at a fast-growing startup that scaled from 150 to 350 employees. - Experience managing a distributed or offshore operations team is strongly preferred. - Strong understanding of multi-state employment compliance and operational risk management. - Experience partnering with external vendors (payroll, benefits, EOR, immigration counsel). - High attention to detail and strong judgment handling confidential employee data. - Strong project management skills and ability to execute against deadlines. PREFERRED QUALIFICATIONS: - Experience managing EOR platforms (Deel, Remote, Rippling Global, Oyster, Papaya, etc.). - Familiarity with immigration support processes and vendor coordination. - Experience in a high-growth startup environment. - HRIS expertise and comfort driving process automation. While we appreciate your interest and application, only applicants under consideration will be contacted. 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 recruiting@jerry.ai recruiting@getjerry.com 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.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.