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UpsideUpsideWashington, DC

Benefits & Payroll Lead

Lead payroll and benefits operations for a growing company, managing end-to-end semi-monthly payroll across multiple states and overseeing comprehensive benefits programs while ensuring compliance.

153k – 183k
Hybrid8+ YOEPeople Ops

About the role

Payroll

  • Manage and execute end-to-end semi-monthly payroll for 250+ U.S.-based employees across 30 states, ensuring accuracy in earnings, deductions, and taxes
  • Handle regular and off-cycle payroll, including bonuses, equity, terminations, and other complex scenarios
  • Own payroll tax compliance across federal, state, and local jurisdictions, including filings, reconciliations, audits, and resolution of tax notices
  • Lead 401(k) audits and workers’ compensation filings
  • Oversee quarterly and annual filings (e.g., 941s, FUTA, SUTA) and ensure timely reporting
  • Partner with Finance on payroll accounting, accruals, journal entries, and close processes
  • Maintain strong internal controls and documentation to support compliance and audit readiness
  • Continuously improve payroll workflows, systems configuration, and data integrity
  • Support and resolve complex payroll questions and issues

Benefits

  • Oversee the administration of health, retirement, leave, and ancillary benefit programs
  • Lead Open Enrollment planning and execution, including vendor coordination and employee communications
  • Ensure compliance with ERISA, ACA, COBRA, HIPAA, and applicable regulations
  • Manage relationships with brokers and third-party administrators to maintain high service quality
  • Monitor regulatory changes and implement updates as needed
  • Continuously improve benefits workflows, system configuration, and data integrity
  • Support and resolve complex benefits-related questions

What You Bring

  • 8+ years of hands-on experience in payroll and benefits administration in a multi-state environment
  • Experience in independently running payroll operations end-to-end
  • Strong knowledge of U.S. payroll tax regulations and benefits compliance
  • Strong analytical and problem-solving skills
  • High attention to detail and a commitment to accuracy
  • Ability to communicate complex information clearly to a wide range of audiences
  • Sound judgment and discretion when handling sensitive employee data
  • Experience with HRIS and payroll systems (e.g., BambooHR)
  • CPP, CEBS, or similar certifications are a plus

Skills

Payroll AdministrationBenefits AdministrationMulti-State PayrollPayroll Tax ComplianceErisa ComplianceAca ComplianceCobra ComplianceHipaa ComplianceBamboohrHRIS

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