Head of People Ops: Payroll, Benefits & Analytics

Highwire; Connecticut; On-site; USD 120,000 - 180,000; Full time

Job summary

Highwire is seeking a Senior Manager, People Operations to lead payroll, benefits and analytics for a growing multistate team. You will partner with Finance and HR to ensure accurate payroll, tax filings, and compliant benefit programs across multiple states.

You will translate complex payroll and workforce data into actionable insights, strengthen People-Finance controls, and drive communication strategies employees value.

Qualifications

• Experience leading payroll, tax, benefits and analytics for a multi-state workforce.
• Ability translate workforce data into actionable insights for senior leaders.
• Strong controls and audit mindset across People and Finance processes.

Responsibilities

• Own end-to-end payroll administration for a multi-state workforce, including off-cycle payrolls and changes.
• Serve as HR/payroll SBOM for Rippling, including configurations and integrations.
• Lead payroll tax administration and compliance across jurisdictions.
• Design and administer health, welfare, and retirement programs with communications plans.
• Oversee 401(k) administration, audits and data integrity.
• Manage leave-of-absence processes and related compliance.
• Build and advance HR analytics dashboards and workforce insights.

Skills

Payroll management

Tax compliance

Benefits administration

People analytics

Cross-functional collaboration

Rippling experience

Tools

Rippling

Job description

Highwire is seeking a Senior Manager, People Operations to lead payroll, benefits and analytics for a growing multistate team. You will partner with Finance and HR to ensure accurate payroll, tax filings, and compliant benefit programs across multiple states.

You will translate complex payroll and workforce data into actionable insights, strengthen People-Finance controls, and drive communication strategies employees value.