HR Operations Generalist: Multi-State Compliance & AI

Jerry; Chicago (IL); Remote; USD 90,000 - 120,000; Full time

Benefits offered by this job

Equity opportunities

Comprehensive benefits package

Remote-friendly environment

Office options in major cities

Job summary

Jerry.ai is seeking an experienced HR Generalist to own multi-state compliance, policy drafting, and payroll/benefits questions. You will lead the annual compliance audit, support HR operations, and reshape processes with an AI-native mindset.

You will be the go-to person for complex compliance issues in a small, fast-paced team, enabling smarter use of AI to reduce busywork and focus on high-impact decisions.

Qualifications

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

Responsibilities

• Own multi-state compliance, policy updates, and implementation across employee classifications.
• Lead annual compliance audit and handbook refresh within 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 ops ownership over time.

Skills

Multi-state compliance

Policy drafting

Payroll & Benefits

AI in HR

Education

Bachelor’s degree in any discipline

Job description

Jerry.ai is seeking an experienced HR Generalist to own multi-state compliance, policy drafting, and payroll/benefits questions. You will lead the annual compliance audit, support HR operations, and reshape processes with an AI-native mindset.

You will be the go-to person for complex compliance issues in a small, fast-paced team, enabling smarter use of AI to reduce busywork and focus on high-impact decisions.