Senior People Operations Leader: Payroll, Benefits & Analytics

Highwire; New York, Northern (NY, KY); Hybrid; USD 100,000 - 125,000; Full time

Benefits offered by this job

Hybrid work model

401(k) matching

Job summary

Highwire is seeking a Senior Manager, People Operations (Payroll, Benefits & Analytics) in New York to lead payroll, benefits design, and people analytics. This hands‑on leader collaborates with People, Finance and operations to deliver accurate payroll, robust benefits programs and data‑driven workforce insights.

The role requires deep expertise in multistate payroll, Rippling administration, and 401(k) management, plus strong communication with executives, brokers and employees.

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 and administering multistate payroll through Rippling is required, including payroll processing, employee and tax setup, deductions, reporting, configuration, integrations and complex issue resolution.
• Experience managing a payroll‑provider relationship, including vendor performance, service delivery and issue 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, compliance and employee communication.
• Hands‑on experience administering a 401(k) or other qualified retirement plan and executing annual plan audits, compliance testing and Form 5500 support.
• Experience overseeing multistate leave administration and coordinating statutory, company, disability, payroll and benefits requirements.
• Advanced people analytics capability, including experience building dashboards, interpreting complex datasets, developing workforce models and presenting actionable recommendations.
• Strong financial acumen and experience partnering with Finance or Accounting on reconciliations, general ledger activity, audits, forecasting and workforce cost analysis.
• Advanced proficiency in Excel or Google Sheets, including complex formulas, pivot tables, lookups, data validation and financial or workforce modeling.
• Strong HR systems expertise, including configuration, workflows, integrations, automation, reporting and data governance.

Responsibilities

• Own end-to-end administration of accurate, timely and compliant multistate payroll including regular and off-cycle payrolls, deductions, changes and garnishments.
• Serve as payroll SME and Rippling administrator: configuration, setup, reporting, integrations and issue resolution.
• Lead payroll tax administration, registrations, filings, notices, year‑end processing, W‑2s and jurisdictional requirements.
• Maintain payroll controls, documentation and audit trails to reduce risk and ensure data accuracy.
• Partner with Finance on funding, mapping, reconciliations, accruals, forecasts and cost reporting.
• Monitor regulatory developments and translate changes into compliant practices and communications.
• Lead benefits strategy, plan design, evaluation and administration; manage renewals and vendor relationships.
• Develop open enrollment communications and educate employees on plans and changes.
• Own 401(k) plan administration, audits and Form 5500 support; coordinate with recordkeepers and third parties.
• Oversee leave-of-absence administration across multistate workforce with timely, compliant guidance.

Skills

Multistate payroll

Payroll tax

Benefits design

People analytics

Financial acumen

Excel/Sheets

HR systems (Rippling)

Vendor management

Communication

Education

Bachelor’s degree in HR/Business/Finance/Accounting/Analytics

Tools

Rippling

HRIS

Job description

Highwire is seeking a Senior Manager, People Operations (Payroll, Benefits & Analytics) in New York to lead payroll, benefits design, and people analytics. This hands‑on leader collaborates with People, Finance and operations to deliver accurate payroll, robust benefits programs and data‑driven workforce insights.

The role requires deep expertise in multistate payroll, Rippling administration, and 401(k) management, plus strong communication with executives, brokers and employees.