Senior People Operations Manager

Jerry Technologies Inc.

Job Overview

Location

Palo Alto, California

Job Type

Full-time

Full Job Description

📋 Description

• Lead the operational foundation of the People function by owning end-to-end payroll processing, tax withholding, and year-end reporting (W-2s) for all employee populations across multiple states and internationally.
• Manage the full lifecycle of employee benefits programs, including open enrollment, vendor performance evaluation, broker relations, and retirement plan administration.
• Oversee global workforce operations by coordinating with EOR partners (e.g., Deel, Remote, Rippling Global) to ensure compliant international hiring, contract management, and cost forecasting in alignment with Finance.
• Build and maintain HRIS data integrity by implementing automation, self-service tools, and AI-driven process optimizations to reduce manual work and scale operations efficiently.
• Design and enforce service-level agreements (SLAs), quality standards, and workflows for onboarding, offboarding, payroll, and benefits support to ensure consistent, accurate, and scalable employee service delivery.
• Lead, coach, and structure a distributed offshore People Operations team of two direct reports in the Philippines, ensuring accountability, clarity, and high-quality execution of daily workflows.
• Own the compliance calendar for federal, state, and local employment regulations, including audit readiness, documentation accuracy, and regulatory updates related to payroll and employment law.
• Coordinate immigration filings, visa tracking, and work authorization support by partnering with legal counsel to manage mobility risks and ensure compliance with immigration requirements.
• Streamline employee lifecycle handoffs between People Ops, IT, and Legal teams to ensure seamless onboarding and offboarding experiences with proper system access, equipment provisioning, and documentation.
• Proactively identify operational risks and implement controls to minimize errors, escalate issues before they impact employees, and maintain high levels of employee trust in People operations.
• Drive continuous improvement in HR processes by leveraging technology, automating repetitive tasks, and embedding best practices in documentation, reporting, and cross-functional collaboration.
• Partner closely with the HR Business Partner lead to ensure operational systems align with strategic priorities in talent density, performance management, and leadership support.
• Ensure all People Operations activities are audit-ready at all times, with complete, accurate, and secure documentation of employee records, payroll transactions, and compliance activities.
• Maintain strict confidentiality and judgment when handling sensitive employee data, ensuring adherence to data privacy standards and internal policies.
• Scale the People Ops function to support rapid company growth, transitioning from reactive execution to a proactive, service-oriented, and data-informed operational model.
• Monitor and optimize EOR and immigration workflows to ensure predictability, low risk, and cost efficiency as the company expands its global footprint.
• Implement metrics and KPIs to measure operational performance, including payroll accuracy rates, benefits utilization, employee support resolution times, and team productivity.

🎯 Requirements

• 7+ years of progressive People Operations experience, including ownership of payroll, benefits, and compliance at a fast-growing startup scaling from 150 to 350 employees
• Experience managing a distributed or offshore operations team
• Strong understanding of multi-state employment compliance and operational risk management
• Experience partnering with external vendors for payroll, benefits, EOR, and immigration counsel
• High attention to detail and strong judgment handling confidential employee data
• Strong project management skills and ability to execute against deadlines

🏖️ Benefits

• Health, dental, and vision coverage
• Paid time off
• Paid parental leave
• 401(k) plan with employer matching
• Wellness benefits
• Equity grants as part of total compensation package

Skills & Technologies

Senior

Remote

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Jerry Technologies Inc.

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About Jerry Technologies Inc.

Jerry Technologies offers a mobile-first AI platform that automatically compares insurance quotes, refinances auto loans, and shops for home and renters coverage. Users submit photos of existing policies, and the app retrieves and compares rates from carriers to find lower premiums or better terms. The company earns commissions from insurers when policies are switched or originated through its platform, serving consumers seeking to reduce recurring auto and home expenses without manual comparison shopping.

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