[Hiring] Senior People Operations Manager @Jerry.ai

Role Description

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
• 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
• Ontario, Canada

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

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.

Requirements

• Lead a distributed offshore People Ops team; provide coaching and structure to two direct reports.
• Establish workflows, quality standards, and SLAs for onboarding, payroll, and benefits.
• Drive HRIS data integrity, automation, and self-service to reduce manual work and scale operations.
• Oversee end-to-end payroll processing, tax withholding, and year-end reporting (W-2s) for all populations.
• Lead open enrollment and manage the full suite of health and retirement programs, vendor performance, and broker relations.
• Manage EOR partnerships for international employees, including contract updates and cost forecasting with Finance.
• Own the compliance calendar (federal, state, local) and lead audits for payroll and documentation.
• Oversee onboarding/offboarding execution and streamline operational handoffs with IT and Legal.
• Coordinate with counsel to manage immigration filings, visa tracking, and work authorization support.

Benefits

• Comprehensive benefits package including health, dental, and vision coverage.
• Paid time off.
• Paid parental leave.
• 401(K) plan with employer matching.
• Wellness benefits.
• Equity opportunities may also be part of your total rewards package.