
Payroll and Benefits Lead
Upside
full-time
Posted on:
Location Type: Hybrid
Location: Washington, D.C. • District of Columbia • Washington • United States
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Salary
💰 $153,000 - $183,000 per year
Job Level
Tech Stack
About the role
- 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
- 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
Requirements
- 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
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
payroll managementpayroll tax compliancebenefits administrationpayroll accountingdata integrityregulatory complianceauditingworkflow improvementanalytical skillsproblem-solving
Soft Skills
attention to detailcommunicationjudgmentdiscretionleadershipcollaborationorganizational skillscustomer serviceadaptabilitycritical thinking
Certifications
CPPCEBS