AI-Driven HR Generalist: Multi-State Compliance

Jerry.ai; Milton (MA); Remote; USD 120,000 - 170,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

Paid time off

Parental leave

401(k) plan with employer matching

Wellness benefits

Job summary

Jerry.ai is a remote-first company building the first AI-powered advisor to manage all your HR operations. You will own multi-state compliance, policy drafting, and the payroll/benefits questions that arise when the handbook doesn’t have all the answers.

You’ll work hands-on in a small, high-intensity team, shaping processes and evaluating AI-native approaches so busywork yields to judgment and impact. This role grows into day-to-day HR operations leadership.

Qualifications

• 2+ years of real, hands-on HR generalist experience, including policy drafting and payroll processing.
• Genuine in-house multi-state compliance experience.
• Comfortable in a small, high-intensity team handling payroll, benefits and compliance.
• Open to building with AI in HR ops.

Responsibilities

• Own multi-state compliance and policy updates across employee 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.
• Rearchitect HR ops processes with AI-native mindset.
• Grow into day-to-day HR operations management over time.

Skills

HR generalist experience

In-house multi-state compliance

Education

Bachelor’s degree

Job description

Jerry.ai is a remote-first company building the first AI-powered advisor to manage all your HR operations. You will own multi-state compliance, policy drafting, and the payroll/benefits questions that arise when the handbook doesn’t have all the answers.

You’ll work hands-on in a small, high-intensity team, shaping processes and evaluating AI-native approaches so busywork yields to judgment and impact. This role grows into day-to-day HR operations leadership.