AI-native HR operations work defines this Jerry.ai People Operations Generalist role, focused on rethinking processes, compliance, and complex employee support. Remote work is supported for most roles.
Jerry.ai needs a hands-on generalist to reduce repetitive HR work and strengthen operational judgment. You will rethink how HR operations should work with AI, while handling multi-state compliance, policy drafting, and escalated payroll, advantages, and leave questions. The role also includes leading the annual compliance audit and handbook refresh, unblocking Payroll and HR Administration team members, and developing toward day-to-day HR operations ownership. Candidates should bring at least two years of practical, in-house HR generalist experience and genuine multi-state compliance experience. Jerry.ai is expanding across physical-asset verticals including home, motorcycle, RV, and boat.
Key Responsibilities:
- Rethink HR operations processes with an AI-native approach
- Review and unblock Payroll and HR Administration work
- Handle complex payroll, benefits, and leave escalations
- Lead compliance audits and handbook refreshes
- Implement policy updates across employee classifications
Requirements:
- Bachelor’s degree in any discipline
- At least two years of hands-on generalist experience
- In-house experience managing multi-state compliance
- Comfort building with AI in HR operations
- Experience working hands-on with payroll and benefits
Use practical HR judgment and AI thinking to improve operations, compliance, payroll support, and employee processes at Jerry.ai.
📌 HR Operations AI Generalist (Toronto)
🏢 Jerry
📍 Toronto