People Operations Leader: AI-Driven Payroll & Onboarding

OVERJET; San Mateo (CA); Hybrid; USD 120,000 - 180,000; Full time

Benefits offered by this job

Competitive Compensation and Equity

Hybrid workplace with flexible in‑per​

401k with matching

Medical, Dental and Vision coverage

Life and AD+D Insurance

8 weeks Paid Parental Leave

Optional HSA with Employer contributed

Flexible Time Off and company paidholi

Job summary

Overjet hires for a pivotal People Operations role in San Mateo. You will own payroll systems, onboarding, offboarding, benefits, and HRIS data hygiene, ensuring workflows run smoothly and data stays clean.

You will coordinate multi-state US payroll, support EoR processes, and drive AI-enabled automation across people operations. A focus on system thinking and clear communication is essential.

Qualifications

• 4–5 years in People Operations or HR Generalist, startup or high-growth.
• Proven Rippling ownership: workflows, modules, payroll, data integrity.
• Multi-state payroll experience; international EoR familiarity strongly preferred.
• Active AI tool user—Claude or similar.
• Benefits administration experience with open enrollment.
• Ability to manage competing priorities and deadlines.
• Discretion with sensitive information and compensation data.
• Clear, direct communicator, both written and verbal.

Responsibilities

• Own Rippling end-to-end: configurations, workflows, integrations, data integrity, reporting.
• Run multi-state US payroll accurately and on time, every cycle.
• Manage EoR coordination and onboarding for PK/EGY.
• Administer benefits programs: open enrollment, carrier relationships, inquiries, plan updates.
• Maintain HRIS data hygiene: org chart accuracy, records updates, audit readiness.
• Own onboarding end-to-end: pre-Day-1 setup, Overjet 101, equipment provisioning, 30/60/90 checks, buddy program.
• Own offboarding: access revocation, asset retrieval, exit docs, final pay.
• Maintain and update employee handbook and HR policies.
• Serve as first HR contact for questions; payroll discrepancies, benefits, leave, policy clarifications.
• Build Serval workflows to automate responses.

Skills

Rippling ownership

Payroll management

Multi-state payroll

AI tools

Benefits administration

Communication

Discretion

Time management

Tools

Rippling

Ashby

Deel

HRIS

Job description

Overjet hires for a pivotal People Operations role in San Mateo. You will own payroll systems, onboarding, offboarding, benefits, and HRIS data hygiene, ensuring workflows run smoothly and data stays clean.

You will coordinate multi-state US payroll, support EoR processes, and drive AI-enabled automation across people operations. A focus on system thinking and clear communication is essential.