via Greenhouse · 10 September 2026 ·9 days ago

Senior Manager, People Operations (Payroll, Benefits & Analytics)

highwire
California
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<p><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">The Senior Manager, People Operations is a highly experienced, hands-on leader responsible for three critical areas of Highwire’s People function: <strong>payroll and payroll tax; benefits and retirement programs; and people analytics</strong>. </span></p>
<p><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">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.</span></p>
<p><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">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.</span></p>
<h2><span style="font-size: 12pt; font-family: verdana, geneva, sans-serif;"><strong>Key Responsibilities</strong></span></h2>
<h3><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><strong> Payroll, Tax and Financial Operations</strong></span></h3>
<ul>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">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.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">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.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Manage the relationship with Rippling, monitor service performance and coordinate the timely resolution of payroll, tax, system and integration issues.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Lead federal, state and local payroll tax administration, including registrations, filings, notices, amendments, quarter-end and year-end processing, W-2s and jurisdictional requirements.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Maintain rigorous payroll controls, review protocols, documentation and audit trails that reduce risk and ensure data accuracy.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Research and resolve complex payroll, tax, timekeeping and pay-related matters with urgency, discretion and clear employee communication.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Partner closely with Finance on payroll funding, general ledger mapping, reconciliations, accruals, invoices, workforce cost reporting, audits and forecasting.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Monitor regulatory developments and translate changes into compliant payroll practices, system configurations and employee communications.</span></li>
</ul>
<h3><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><strong> Benefits Strategy, Plan Design and Communication</strong></span></h3>
<ul>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">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.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Partner with brokers, carriers and Finance on renewals, plan modeling, employee contribution strategy, vendor selection, implementation and ongoing performance management.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Analyze claims, utilization, enrollment, benchmarking and employee feedback to evaluate plan performance and recommend thoughtful program enhancements.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Develop and execute a year-round benefits communication and education strategy, including open enrollment, plan changes, decision-support resources and targeted campaigns.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Translate complex benefit information into clear, accessible and engaging communications that help employees understand and use their programs effectively.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Own benefit administration and compliance, including eligibility, deductions, reconciliations, required notices and applicable ACA, COBRA, ERISA, HIPAA and Section 125 requirements.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Manage broker, carrier and vendor relationships, service levels, contracts and issue escalation while holding partners accountable for performance.</span></li>
</ul>
<h3><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><strong> 401(k) Administration and Audit Execution</strong></span></h3>
<ul>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Serve as the primary administrator for Highwire’s 401(k) plan, managing eligibility, enrollment, contributions, loans, distributions, corrections and employee inquiries.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Partner with the plan recordkeeper, third-party administrator, Finance and payroll to ensure accurate data, timely contribution remittance and strong plan controls.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Lead annual compliance testing, census preparation, required notices and other plan governance activities.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Own the execution of the annual 401(k) audit, including auditor coordination, requested documentation, census and transaction data, reconciliations and issue resolution.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Support Form 5500 preparation and filing and ensure audit or compliance findings are resolved promptly and sustainably.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Monitor regulatory and plan developments and recommend improvements to plan design, administration and employee education.</span></li>
</ul>
<h3><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><strong> Leave-of-Absence Administration</strong></span></h3>
<ul>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Oversee end-to-end leave-of-absence administration for Highwire’s multistate workforce, including federal, state and company-sponsored leaves and disability programs.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Provide clear, compassionate and consistent guidance to employees and managers throughout the leave process.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Coordinate documentation, required notices, payroll, benefit deductions, disability payments, job protection and return-to-work requirements.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-serif;">Partner with employees, managers, payroll, benefit carriers and external administrators to ensure leaves are handled accurately, promptly and compliantly.</span></li>
<li style="font-size: 10pt; font-family: verdana, geneva, sans-serif;"><span style="font-size: 10pt; font-family: verdana, geneva, sans-seri

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