Senior Manager, People Operations – Payroll, Benefits, Analytics

This is a fully remote position, open to applicants in California, +3 more states.

📋 Description

• Take full responsibility for ensuring timely, accurate, and compliant semi-monthly payroll for a multistate workforce.

• Oversee Rippling payroll configuration, including employee and tax setup, reporting, integrations, and resolving issues.

• Manage the relationship with Rippling, facilitating coordination for payroll, tax, system, and integration issue resolution.

• Direct federal, state, and local payroll tax administration, including filings, notices, amendments, and year-end processing.

• Maintain payroll controls along with review protocols, documentation, and audit trails.

• Collaborate with the Finance team on payroll funding, general ledger mapping, reconciliations, accruals, invoices, audits, forecasting, and workforce cost reporting.

• Spearhead the strategy, plan design, financial evaluation, and administration of health, welfare, and related benefits.

• Oversee brokers, carriers, and vendors, managing renewals, plan modeling, vendor selection, and performance.

• Create benefits communications, open enrollment materials, and employee education resources.

• Ensure benefits compliance with regulations such as ACA, COBRA, ERISA, HIPAA, and Section 125 requirements.

• Manage the 401(k) plan, covering eligibility, enrollment, contributions, loans, distributions, corrections, and inquiries.

• Lead annual retirement plan compliance testing, notices, governance activities, and the execution of 401(k) audits.

• Assist in the preparation and filing of Form 5500.

• Supervise multistate leave-of-absence administration, coordinating documentation, payroll, benefits, disability payments, and return-to-work requirements.

• Develop people analytics dashboards, recurring reports, and executive-ready workforce insights.

• Track workforce metrics, including headcount, labor cost, turnover, retention, engagement, promotions, performance, composition, recruiting, benefits, and leave.

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

• Manage payroll-related Rippling workflows, permissions, reporting, and integrations.

• Establish data standards, operating procedures, and quality controls across People systems.

• Conduct audits, resolve discrepancies, and drive scalable process and technology improvements.

• Lead complex cross-functional initiatives and handle change communication.

⛳️ Requirements

• Minimum of seven years of progressive experience in multistate payroll, payroll tax, benefits, leave administration, HR systems, people analytics, and People-Finance operations.

• Direct, hands-on experience with processing and administering multistate payroll using Rippling, including payroll processing, employee and tax setup, deductions, reporting, configuration, integrations, and resolving complex issues.

• Proven experience managing a payroll-provider relationship, covering vendor performance, service delivery, and issue escalation.

• Extensive knowledge of multistate payroll and payroll tax requirements, including quarter-end and year-end processing.

• Demonstrated experience in leading benefits plan design, renewals, financial analysis, administration, compliance, and communicating with employees.

• Hands-on experience with administering a 401(k) or other qualified retirement plans, including executing annual plan audits, compliance testing, and supporting Form 5500.

• Experience in overseeing multistate leave administration and coordinating statutory, company, disability, payroll, and benefits requirements.

• Advanced people analytics skills, including the development of dashboards, interpretation of complex datasets, workforce modeling, and presenting actionable recommendations.

• Strong financial acumen with experience collaborating with Finance or Accounting on reconciliations, general ledger activities, 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 expertise in HR systems, including configuration, workflows, integrations, automation, reporting, and data governance.

• Excellent written and verbal communication skills.

• Exceptional judgment, organizational skills, and attention to detail, with the ability to manage competing priorities and maintain confidentiality.

• Bachelor’s degree in human resources, business, finance, accounting, analytics, or a related field, or equivalent professional experience.

• Preferred: Certified Payroll Professional (CPP) certification.

• Preferred experience in professional services, agency, private equity-backed, or similarly fast-paced distributed organizations.

• Preferred experience supporting mergers and acquisitions.

• Preferred experience evaluating or administering self-funded or level-funded health plans.

• Preferred experience leading payroll, benefits, HRIS, or vendor implementations.

• Must reside in an eligible listed location at the time of hire.

🏝️ Benefits

• Competitive benefits package that includes medical, dental, and vision coverage.

• 401(k) matching program.

• Generous paid time off policy.

• Additional well-being and growth perks.

• Competitive salary with merit-based opportunities for advancement.

• Flexible hybrid work model customized to fit your schedule and lifestyle.

• Extended summer and winter breaks.

• Early Friday log-off through Empower Hours.

• Flexible Spending Account (FSA) options.

• Paid parental leave.

• Commuter benefits.

• Annual Growth Mindset stipend for books, events, or learning experiences.

• Monthly technology reimbursement.

• Wellness benefit program aimed at promoting mental and physical health.

• 501c3 donation matching program.

• Opportunities for mentorship and ongoing professional development.

• Monthly recognition and team celebrations.

• Employee referral and new business referral bonuses.

• Quarterly Highwire events and team gatherings.

• Dog-friendly office environment.

• Supportive, inclusive, and collaborative workplace culture.