Payroll and Benefits Lead

Upside•Washington, DC

5d•$153,000 - $183,000•Hybrid

About The Position

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives. About the Role We’re bringing together our payroll and benefits functions into a single, high-impact role - and we’re looking for someone who’s excited to help shape and strengthen how we support our employees! Reporting to the Senior Director of Total Rewards, the Benefits & Payroll Lead will play a key role on our People Team. You’ll ensure our payroll and benefits programs run smoothly, stay compliant, and are easy for employees to understand and trust. You’ll be a go-to partner for employees and a driver of operational excellence - both in the day-to-day details and in improving how our systems scale over time. This is a great opportunity to take ownership and help shape how these programs evolve as we grow.

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)

Nice To Haves

CPP, CEBS, or similar certifications are a plus

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