Senior Manager, People Operations; Payroll Analytics

The Senior Manager, People Operations is a highly experienced, hands‑on leader responsible for three critical areas of Highwire’s People function:
payroll and payroll tax; benefits and retirement programs; and people analytics
.

This role sits at the intersection of People, Finance and business operations. It translates complex workforce and financial data into actionable insights, strengthens the controls connecting People and Finance, and designs benefits programs and communication strategies that employees can understand and value.

The ideal candidate combines deep technical expertise with strong business judgment, exceptional attention to detail and the ability to move fluidly between strategy and execution. This person will serve as a trusted partner to People leadership, Finance, senior leaders, brokers, vendors and employees while continuously improving the systems and processes that support our growing, multistate workforce.

• Own the end-to-end administration of accurate, timely and compliant semi-monthly payroll for a multistate workforce, including regular and off-cycle payrolls, variable compensation, deductions, garnishments and employee changes.
• Serve as Highwire’s internal payroll subject‑matter expert and primary administrator for Rippling, our payroll provider, including payroll configuration, employee and tax setup, reporting, integrations and issue resolution.
• Manage the relationship with Rippling, monitor service performance and coordinate the timely resolution of payroll, tax, system and integration issues.
• Lead federal, state and local payroll tax administration, including registrations, filings, notices, amendments, quarter‑end and year‑end processing, W-2s and jurisdictional requirements.
• Maintain rigorous payroll controls, review protocols, documentation and audit trails that reduce risk and ensure data accuracy.
• Research and resolve complex payroll, tax, timekeeping and pay-related matters with urgency, discretion and clear employee communication.
• Partner closely with Finance on payroll funding, general ledger mapping, reconciliations, accruals, invoices, workforce cost reporting, audits and forecasting.
• Monitor regulatory developments and translate changes into compliant payroll practices, system configurations and employee communications.

• Lead the strategy, design, financial evaluation and administration of Highwire’s health, welfare and related benefit programs, balancing employee value, market competitiveness, cost and organizational priorities.
• Partner with brokers, carriers and Finance on renewals, plan modeling, employee contribution strategy, vendor selection, implementation and ongoing performance management.
• Analyze claims, utilization, enrollment, benchmarking and employee feedback to evaluate plan performance and recommend thoughtful program enhancements.
• Develop and execute a year‑round benefits communication and education strategy, including open enrollment, plan changes, decision‑support resources and targeted campaigns.
• Translate complex benefit information into clear, accessible and engaging communications that help employees understand and use their programs effectively.
• Own benefit administration and compliance, including eligibility, deductions, reconciliations, required notices and applicable ACA, COBRA, ERISA, HIPAA and Section 125 requirements.
• Manage broker, carrier and vendor relationships, service levels, contracts and issue escalation while holding partners accountable for performance.

• Serve as the primary administrator for Highwire’s 401(k) plan, managing eligibility, enrollment, contributions, loans,…