People Operations Lead — Payroll & Systems (Hybrid, San Mateo)

Overjet; San Mateo (CA); Hybrid; USD 90,000 - 130,000; Full time

Benefits offered by this job

Medical, Dental and Vision coverage

401k with matching

Eight weeks Paid Parental Leave

Equity

Hybrid workplace

Learning and Development stipend

Job summary

Overjet is seeking a proactive People Operations generalist to own payroll, onboarding, benefits, and HR program administration from the San Mateo office. You will implement scalable systems, maintain data integrity, and partner with leadership to build a people-focused organization.

You will work across HRIS, payroll, and admin tasks, leveraging AI tools to automate repetitive workflows and improve processes. This role requires multi-state payroll experience and strong communication.

Qualifications

• 4–5 years of People Operations or HR Generalist experience, with startup/high-growth background.
• Proven Rippling ownership — built workflows, configured modules, ran payroll, and kept data clean.
• Multi-state payroll experience; international EoR familiarity (Deel or equivalent) preferred.
• Active AI tool user — Claude or similar, to automate tasks and surface insights.
• Benefits administration experience: open enrollment and broker relations.

Responsibilities

• Own end-to-end payroll and HRIS systems, ensuring data integrity and reporting.
• Lead onboarding and offboarding processes, equipment provisioning, and orientation coordination.
• Manage benefits programs, enrollment cycles, and employee inquiries.
• Maintain and update employee handbook and HR policies as the company grows.
• Support workplace operations in San Mateo and coordinate office experiences.
• Build integrations between Rippling, Ashby, and other HR tools; automate workflows using AI.

Skills

People Operations

Rippling ownership

Multi-state payroll

AI tools Claude

Benefits administration

Discretion with data

Strong communication

Tools

Rippling

Ashby

Deel

Claude

Job description

Overjet is seeking a proactive People Operations generalist to own payroll, onboarding, benefits, and HR program administration from the San Mateo office. You will implement scalable systems, maintain data integrity, and partner with leadership to build a people-focused organization.

You will work across HRIS, payroll, and admin tasks, leveraging AI tools to automate repetitive workflows and improve processes. This role requires multi-state payroll experience and strong communication.