People Operations Lead: Payroll, Benefits & Analytics

Highwire; Chicago (IL); Hybrid; USD 90,000 - 110,000; Full time

Benefits offered by this job

401(k) with employer matching

Medical, dental, vision coverage

Paid parental leave

Monthly technology reimbursement

Job summary

Highwire is seeking a Senior Manager, People Operations to lead payroll, benefits and analytics for a multistate workforce. You will own end‑to‑end payroll administration, including taxes, deductions and changes, while serving as the Rippling expert and ensuring data accuracy and compliance.

You will also design and administer health, welfare and retirement programs, analyze plan performance, and communicate complex information clearly to employees and senior leaders.

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, 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.
• Excellent written and verbal communication skills, including the ability to make technical payroll, benefits and data concepts understandable to employees and senior leaders.
• Exceptional judgment, organization and attention to detail, with the ability to manage competing priorities and highly confidential information.

Responsibilities

• Own end-to-end payroll administration for multistate workforce, including regular and off-cycle payrolls, deductions and employee changes.
• Serve as the internal payroll subject-matter expert and primary Rippling administrator, including configuration and reporting.
• Lead federal, state and local payroll tax administration, filings, notices and year-end processing.
• Maintain payroll controls, documentation and audit trails to reduce risk and ensure data accuracy.
• Partner with Finance on funding, GL mapping, reconciliations, and cost reporting.
• Monitor regulatory developments and translate changes into compliant payroll practices and communications.
• Lead benefits strategy, design and administration across health, welfare and related programs.
• Manage broker/vendor relationships, renewals, modeling, and performance management.
• Oversee 401(k) plan administration, audits and Form 5500 support; ensure data integrity across plan governance.
• Lead leave-of-absence administration for multistate workforce and ensure compliance.

Skills

Multistate payroll

Payroll tax

Benefits programs

People analytics

HR systems

People–Finance collaboration

Education

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

Tools

Rippling

Job description

Highwire is seeking a Senior Manager, People Operations to lead payroll, benefits and analytics for a multistate workforce. You will own end‑to‑end payroll administration, including taxes, deductions and changes, while serving as the Rippling expert and ensuring data accuracy and compliance.

You will also design and administer health, welfare and retirement programs, analyze plan performance, and communicate complex information clearly to employees and senior leaders.