HR Generalist — AI-Driven HR Ops & Multi-State Compliance

Jerry; Chicago (IL); Remote; USD 70,000 - 90,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

PTO (Paid Time Off)

Parental leave

401K with employer matching

Wellness benefits

Job summary

Jerry.ai is seeking an experienced HR Operations Manager to own multi-state compliance, policy drafting, and payroll/benefits questions. You will work hands-on in a fast-growing startup, shaping how HR operates as we expand into new states and verticals, with room to apply AI-driven approaches.

You will partner with Finance and People teams, lead audits, and refine our handbook while maintaining equitable, compliant processes across all employee types.

Qualifications

• Bachelor's degree in any discipline.
• At least 2 years of hands-on HR generalist experience.
• In-house, multi-state compliance experience.
• Proactive payroll, benefits, and compliance tasks.
• Eager to build with AI in HR operations.

Responsibilities

• Own multi-state compliance tracking and policy updates.
• Lead annual compliance audit and handbook refresh.
• Handle escalated payroll, benefits, and leave questions.
• Review and unblock Payroll and HR Administration team.
• Rearchitect HR ops processes with an AI-native mindset.
• Grow into day-to-day HR operations ownership.

Skills

HR generalist

Policy drafting

Payroll administration

Compliance management

AI in HR

Multi-state compliance

Education

Bachelor's degree

Job description

Jerry.ai is seeking an experienced HR Operations Manager to own multi-state compliance, policy drafting, and payroll/benefits questions. You will work hands-on in a fast-growing startup, shaping how HR operates as we expand into new states and verticals, with room to apply AI-driven approaches.

You will partner with Finance and People teams, lead audits, and refine our handbook while maintaining equitable, compliant processes across all employee types.