Payroll and Benefits Lead at Upside overseeing payroll for U.S. employees and benefits administration. Collaborating with teams for operational excellence and compliance in a hybrid work environment.
Responsibilities
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
Benefits
Medical, dental, and vision coverage starting on Day 1
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