HR Operations Generalist — AI-Driven, Multi-State Compliance

Jerry; Boston (MA); Remote; USD 110,000 - 150,000; Full time

Benefits offered by this job

Health, dental, and vision coverage

Paid time off

Parental leave

401(k) plan with employer matching

Remote-friendly work options

Job summary

Jerry.ai is seeking an HR Operations Specialist to own multi-state compliance, policy drafting, and payroll/benefits questions in a fast-growing startup. You’ll work hands-on in-house, with room to bring AI into HR ops, reducing busywork and enabling judgement-based decisions.

As part of a small, high-intensity team, you’ll lead policy updates, coordinate audits, and mentor payroll/HR admins, with opportunities to expand into day-to-day HR operations management over time.

Qualifications

• Bachelor's degree in any discipline.
• 2+ years of hands-on HR generalist experience with policy drafting, payroll, and compliance.
• In-house multi-state compliance experience.
• Comfortable in a small, high-intensity team handling payroll, benefits, and compliance.
• Excited to build with AI in HR operations.

Responsibilities

• Own multi-state compliance, draft policies, and ensure correct pay ranges across classifications.
• Lead annual compliance audit and handbook refresh within first 90 days.
• Handle escalated payroll, benefits, and leave questions.
• Review and unblock work of Payroll and HR Administration team members.
• Rethink HR ops processes with an AI-native mindset.

Skills

HR generalist

Payroll

Benefits administration

Policy drafting

Multi-state compliance

Education

Bachelor's degree

Tools

HRIS

Payroll software

Job description

Jerry.ai is seeking an HR Operations Specialist to own multi-state compliance, policy drafting, and payroll/benefits questions in a fast-growing startup. You’ll work hands-on in-house, with room to bring AI into HR ops, reducing busywork and enabling judgement-based decisions.

As part of a small, high-intensity team, you’ll lead policy updates, coordinate audits, and mentor payroll/HR admins, with opportunities to expand into day-to-day HR operations management over time.