People Operations Generalist (HR Compliance & Payroll)

Jerry; New York (NY); Hybrid; USD 110,000 - 170,000; Full time

Benefits offered by this job

Health, dental, vision coverage

Paid time off

401(k) plan with employer matching

Wellness benefits

Equity opportunities

Job summary

Jerry.ai seeks an HR generalist with hands-on, multi-state compliance experience to own critical HR operations. You’ll draft policies, manage payroll and benefits, and lead compliance activities while integrating AI into HR workflows.

This is a high-impact role in a fast-paced team. You’ll work from a hybrid setup with preference for office presence in Palo Alto, New York, Chicago, or Toronto, and remote options for the right fit.

Qualifications

• Bachelor’s degree in any discipline.
• At least 2 years of real, hands-on HR generalist experience; you’ve drafted policy, processed payroll, and handled compliance filings.
• Genuine in-house, multi-state compliance experience.
• Comfortable in a small, high-intensity team where you touch payroll, benefits, and compliance yourself.
• Excited to build with AI in HR.

Responsibilities

• Multi-state compliance: track state-by-state law changes, draft policy updates, and implement across employee classifications.
• Lead the annual compliance audit and handbook refresh within 90 days.
• Handle escalated payroll, benefits, and leave questions requiring experienced judgment.
• Review and unblock work of Payroll and HR Administration teams.
• Rearchitect HR operations with an AI-native mindset and long-term ownership of tasks.
• Grow into day-to-day HR operations management over time.

Skills

HR generalist

Multi-state compliance

Policy drafting

Payroll

Benefits

AI in HR

Education

Bachelor’s degree in any discipline

Job description

Jerry.ai seeks an HR generalist with hands-on, multi-state compliance experience to own critical HR operations. You’ll draft policies, manage payroll and benefits, and lead compliance activities while integrating AI into HR workflows.

This is a high-impact role in a fast-paced team. You’ll work from a hybrid setup with preference for office presence in Palo Alto, New York, Chicago, or Toronto, and remote options for the right fit.