Senior People Ops Lead: Payroll, Benefits Analytics Remote

Highwire; Washington (District of Columbia); Hybrid; USD 90,000 - 110,000; Full time

Benefits offered by this job

Competitive pay

Hybrid work model

Generous vacation

401(k) matching

Medical, dental, vision

Job summary

Highwire seeks a Senior Manager, People Operations to lead payroll, benefits and analytics for a multistate workforce. The role partners with Finance and People leadership to ensure accurate payroll processing, compliant tax filings, and compelling benefits programs.

You’ll design data-driven insights and manage our Rippling platform, driving scalable, auditable processes across the organization. The ideal candidate combines deep technical expertise with business judgment, strong attention to

Qualifications

• At least seven years of progressive experience across multistate payroll, payroll tax, benefits, leave administration, HR systems, people analytics and People–Finance operations.
• Direct, hands‑on experience processing multistate payroll through Rippling is required, including deductions, reporting, configuration and complex issue resolution.
• Experience managing a payroll-provider relationship, including vendor performance and escalation.
• Deep knowledge of multistate payroll and payroll tax requirements, including quarter‑end and year‑end processing.
• Demonstrated experience leading benefits plan design, renewals, financial analysis, administration and compliance.
• Hands‑on experience administering a 401(k) or other qualified retirement plan and conducting annual plan audits and Form 5500 support.
• Experience overseeing multistate leave administration and coordinating statutory requirements.
• Advanced people analytics capability with dashboards, modeling and insights.
• Strong financial acumen and partnering with Finance on reconciliations, GL activity and cost analysis.
• Excel/Google Sheets proficiency with complex formulas and data modeling.
• HR systems expertise including configuration, workflows, integration and data governance.
• Excellent written and verbal communication skills; ability to explain payroll/benefits concepts clearly.
• Exceptional judgment, organization and attention to detail; ability to manage competing priorities.
• Bachelor’s degree or equivalent professional experience.

Responsibilities

• Oversee multistate payroll and tax administration across states.
• Lead benefits strategy, design and communication.
• Manage 401(k) administration and annual audits.
• Oversee leave-of-absence administration for multistate workforce.
• Advance people analytics capability with dashboards and executive-ready insights.
• Own Rippling configuration, reporting and integrations.
• Collaborate with Finance on reconciliations, forecasts and cost reporting.
• Drive scalable, compliant payroll and benefits programs.

Skills

Multistate payroll

Payroll tax

Benefits administration

Leave administration

HR systems

People analytics

Excel/Google Sheets

Education

Bachelor’s degree or equivalent experience

Tools

Rippling

Job description

Highwire seeks a Senior Manager, People Operations to lead payroll, benefits and analytics for a multistate workforce. The role partners with Finance and People leadership to ensure accurate payroll processing, compliant tax filings, and compelling benefits programs.

You’ll design data-driven insights and manage our Rippling platform, driving scalable, auditable processes across the organization. The ideal candidate combines deep technical expertise with business judgment, strong attention to