Senior Manager, People Operations (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

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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.

Key Responsibilities

Payroll, Tax and Financial Operations

• 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.

Benefits Strategy, Plan Design and Communication

• 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.

401(k) Administration and Audit Execution

• Serve as the primary administrator for Highwire’s 401(k) plan, managing eligibility, enrollment, contributions, loans, distributions, corrections and employee inquiries.


• Partner with the plan recordkeeper, third‑party administrator, Finance and payroll to ensure accurate data, timely contribution remittance and strong plan controls.


• Lead annual compliance testing, census preparation, required notices and other plan governance activities.


• Own the execution of the annual 401(k) audit, including auditor coordination, requested documentation, census and transaction data, reconciliations and issue resolution.


• Support Form 5500 preparation and filing and ensure audit or compliance findings are resolved promptly and sustainably.


• Monitor regulatory and plan developments and recommend improvements to plan design, administration and employee education.

Leave‑of‑Absence Administration

• Oversee end‑to‑end leave‑of‑absence administration for Highwire’s multistate workforce, including federal, state and company‑sponsored leaves and disability programs.


• Provide clear, compassionate and consistent guidance to employees and managers throughout the leave process.


• Coordinate documentation, required notices, payroll, benefit deductions, disability payments, job protection and return‑to‑work requirements.


• Partner with employees, managers, payroll, benefit carriers and external administrators to ensure leaves are handled accurately, promptly and compliantly.


• Maintain confidential leave records, monitor timelines and identify issues requiring escalation or additional support.


• Track leave trends and use insights to improve employee communication, administration and program effectiveness.

People Analytics and Workforce Insights

• Build and advance Highwire’s people analytics capability, including reliable dashboards, recurring reporting and executive‑ready insights that connect workforce trends to business performance.


• Define and monitor key measures across headcount, labor cost, turnover, retention, engagement, promotions, performance, workforce composition, recruiting, benefits and leave.


• Analyze complex datasets to identify patterns, risks and opportunities, moving beyond reporting what happened to explaining why it matters and recommending action.


• Partner with People and Finance leaders on headcount planning, labor forecasting, compensation analysis, workforce cost modeling and scenario planning.


• Create clear and compelling data narratives and visualizations for senior leaders and other stakeholders.


• Establish consistent metric definitions, reporting standards and data governance practices that improve confidence in workforce information.


• Protect the confidentiality and integrity of employee data in all