HR Operations Generalist — AI-Driven Multi-State Compliance

Jerry.ai; Milton (MA); Remote; USD 110,000 - 160,000; Full time

Benefits offered by this job

Health insurance

Dental coverage

Vision coverage

Paid time off

Parental leave

401(k) match

Wellness benefits

Equity opportunities

Job summary

Jerry.ai is seeking a hands-on HR Operations Lead to own multi-state compliance, policy drafting, and payroll/benefits questions as they arise. You’ll navigate complex scenarios in-house, applying practical judgment rather than scripts.

You’ll also guide AI integration into HR ops to reduce busywork and focus on high-impact decisions. You’ll own the annual compliance audit and handbook refresh, and you’ll mentor the Payroll and HR Administration teams as the function evolves toward AI-native

Qualifications

• Bachelor’s degree in any discipline.
• At least 2 years of real, hands-on HR generalist experience.
• 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.

Responsibilities

• Multi-state compliance tracking and policy updates across employee classifications.
• Lead annual compliance audit and handbook refresh start to finish (first 90 days).
• Escalated payroll, benefits, and leave questions requiring experienced hands.
• Reviewing and unblocking work of Payroll and HR Administration team members.
• Rearchitect HR ops processes with an AI-native mindset.

Skills

HR generalist

Multi-state compliance

Payroll handling

Benefits administration

AI in HR

Education

Bachelor's degree

Job description

Jerry.ai is seeking a hands-on HR Operations Lead to own multi-state compliance, policy drafting, and payroll/benefits questions as they arise. You’ll navigate complex scenarios in-house, applying practical judgment rather than scripts.

You’ll also guide AI integration into HR ops to reduce busywork and focus on high-impact decisions. You’ll own the annual compliance audit and handbook refresh, and you’ll mentor the Payroll and HR Administration teams as the function evolves toward AI-native