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HR Operations Generalist; Fully Remote
Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60290, USA
Listed on 2026-10-03
Chicago, Cook County, Illinois, 60290, USA
Listing for:
Jerry.ai
Remote/Work from Home
position Listed on 2026-10-03
Job specializations:
-
HR/Recruitment
Recruiter / Talent Acquisition, HR Generalist / Talent Management, Regulatory Compliance Specialist
Job Description & How to Apply Below
- Own the HR operations work that requires judgment: multi-state compliance, policy drafting, and complex payroll and benefits questions.
- Use AI to cut repetitive work and spend more time on the escalations that need a person.
- Lead the annual compliance audit and handbook refresh end-to-end in your first 90 days.
- Review and unblock the Payroll and HR Administration team as you rearchitect HR ops processes with an AI-native mindset.
- At least two years of hands-on HR generalist experience with genuine in-house multi-state compliance.
- Comfortable in a small, high-intensity team and excited to build with AI.
Jerry is building the first AI-powered advisor to manage all your physical assets, starting with car insurance and expanding into home, motorcycle, RV, and boat. It is a Series C, YC-backed startup with 5M+ customers and $240M in funding, and a small, remote-first team of competitive but kind owners.
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