People Team Senior People Operations Manager Palo Alto, California

About the opportunity: We are hiring a

Senior People Operations Manager

to lead the operational foundation of our People function. This role will own the day-to-day and strategic execution of

payroll, benefits, HR compliance, employment taxes, HR systems, immigration coordination, and global workforce operations (including EOR management).

This role will also

manage a distributed People Operations support team

(two Philippines-based associates) responsible for daily execution and employee support workflows. You will set priorities, ensure operational rigor, and raise the bar on accuracy, documentation, and service delivery as the company scales.

This position partners closely with our HRBP lead, who will focus on employee relations, performance management, talent density, and leadership support—while you ensure the systems and operations behind the employee experience are consistent, compliant, and scalable.

This position can be fully remote from

AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NY, NV, OR, TN, TX, UT, VA, or Ontario, Canada,

or onsite/hybrid from Palo Alto, New York, or Toronto.

People Operations & Team Leadership:

Team Management:

Lead a distributed offshore People Ops team; provide coaching and structure to two direct reports.

Service Delivery:

Establish workflows, quality standards, and SLAs for onboarding, payroll, and benefits.

Process Excellence:

Drive HRIS data integrity, automation, and self-service to reduce manual work and scale operations. Building and utilizing AI tools to automate and optimize HR processes.

Payroll, Benefits & Finance:

Payroll Ownership:

Oversee end-to-end payroll processing, tax withholding, and year-end reporting (W-2s) for all populations.

Benefits Strategy:

Lead open enrollment and manage the full suite of health and retirement programs, vendor performance, and broker relations.

Global Operations:

Manage EOR partnerships for international employees, including contract updates and cost forecasting with Finance.

Compliance, Risk & Lifecycle:

Regulatory Oversight:

Own the compliance calendar (federal, state, local) and lead audits for payroll and documentation.

Employee Lifecycle:

Oversee onboarding/offboarding execution and streamline operational handoffs with IT and Legal.

Mobility:

Coordinate with counsel to manage immigration filings, visa tracking, and work authorization support.

What Success Looks Like:

Payroll and benefits run smoothly, with minimal escalations and high employee trust.

Compliance processes are proactive, organized, and audit-ready at all times.

EOR and immigration workflows are predictable, well-managed, and low-risk.

Associates are well-supported and operating with clarity, accountability, and strong quality standards.

People Ops runs as a scalable service function—fast, accurate, and consistent.

Qualifications:

7+ years of progressive People Operations experience, including payroll, benefits, and compliance ownership at a fast‑growing startup that scaled from 150 to 350 employees.

Experience managing a distributed or offshore operations team is strongly preferred.

Strong understanding of multi‑state employment compliance and operational risk management.

Experience partnering with external vendors (payroll, benefits, EOR, immigration counsel).

High attention to detail and strong judgment handling confidential employee data.

Strong project management skills and ability to execute against deadlines.

Preferred Qualifications:

Experience managing EOR platforms (Deel, Remote, Rippling Global, Oyster, Papaya, etc.).

Familiarity with immigration support processes and vendor coordination.

Experience in a high‑growth startup environment.

HRIS expertise and comfort driving process automation.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job‑related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market‑dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part‑time, contract, or freelance roles may not be eligible for certain benefits.

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