People Ops Generalist: AI-Driven, Multi-State Compliance

Jerry; Chicago (IL); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Jerry.ai is seeking an experienced HR Operations professional to own high-impact, multi-state compliance and policy drafting. You will manage payroll and benefits questions, and guide the HR Administration team with an AI-first approach. This is a hands-on, in-house role in a fast-growing startup.

You will shape day-to-day HR operations, drive process improvements, and collaborate closely with leadership to scale the function across states and roles.

Qualifications

• 2+ years of real, hands-on HR generalist experience including policy drafting, payroll, and compliance
• Genuine in-house, multi-state compliance experience
• Comfortable in a small, high-intensity team where you touch payroll, benefits, and compliance

Responsibilities

• Own multi-state compliance: track law changes, draft policy updates, ensure rollout across classifications and pay ranges
• Lead annual compliance audit and handbook refresh in first 90 days
• Handle escalated payroll, benefits, and leave questions
• Review and unblock work of Payroll and HR Administration team members
• Rearchitect HR ops processes with an AI-native mindset
• Grow into day-to-day HR operations management over time

Skills

HR generalist

Multi-state compliance

Policy drafting

Payroll awareness

Benefits administration

AI in HR

Education

Bachelor's degree

Job description

Jerry.ai is seeking an experienced HR Operations professional to own high-impact, multi-state compliance and policy drafting. You will manage payroll and benefits questions, and guide the HR Administration team with an AI-first approach. This is a hands-on, in-house role in a fast-growing startup.

You will shape day-to-day HR operations, drive process improvements, and collaborate closely with leadership to scale the function across states and roles.