Senior People Ops Leader: Payroll, Benefits & Analytics

Highwire; San Francisco, Northern (CA, KY); Hybrid; USD 100,000 - 125,000; Full time

Benefits offered by this job

Medical, dental and vision coverage

401(k) matching

Generous paid time off

Other employee perks

Job summary

Highwire in San Francisco seeks a Senior Manager, People Operations (Payroll, Benefits & Analytics) to lead payroll, benefits and people data analytics for a multistate workforce. This hands-on leader partners with Finance, HR and vendors to ensure accurate payroll, strong benefits programs and insightful workforce metrics.

The role requires deep technical payroll knowledge, compliance focus, and the ability to translate data into clear communications and strategic programs.

Qualifications

• 7+ years in multistate payroll, benefits and People–Finance operations.
• Experience with Rippling payroll processing, tax setup, and reporting.
• Strong benefits design, renewals, financial analysis and employee communication.
• Experience administering 401(k) plans and annual audits (Form 5500).
• Leave administration across multiple states and regulatory compliance.
• Advanced proficiency in Excel/Google Sheets and data modeling.

Responsibilities

• Own end-to-end payroll administration for multistate workforce, including off-cycle payrolls and deductions.
• Serve as payroll SME for Rippling, including configuration, setup and integrations.
• Coordinate payroll tax filings, notices and year-end processes with Finance.
• Lead design and administration of health, welfare and retirement programs.
• Manage 401(k) plan audits, compliance testing and Form 5500 support.
• Oversee leave-of-absence administration and return-to-work processes.
• Develop workforce analytics dashboards and executive-ready insights.
• Improve People systems, data governance and cross-functional processes.

Skills

Multistate payroll

Payroll tax

Benefits administration

Leave administration

People analytics

Excel/Sheets modeling

HR systems expertise

Vendor management

Education

Bachelor’s degree in HR, business, finance, accounting, analytics or related field

Tools

Rippling

HRIS

Job description

Highwire in San Francisco seeks a Senior Manager, People Operations (Payroll, Benefits & Analytics) to lead payroll, benefits and people data analytics for a multistate workforce. This hands-on leader partners with Finance, HR and vendors to ensure accurate payroll, strong benefits programs and insightful workforce metrics.

The role requires deep technical payroll knowledge, compliance focus, and the ability to translate data into clear communications and strategic programs.