Benefits & Payroll Lead

Meet Upside: 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. 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 How You Work / What Sets You Apart - Consistent delivery with measurable impact. You reliably execute on critical processes and continuously improve them, using data to identify opportunities and track outcomes. - Effective stakeholder partnership. You build strong, trusted relationships across teams (especially Finance and People), and collaborate to solve problems and drive alignment. - Operational discipline. You bring structure, organization, and rigor to your work, with a focus on accuracy, documentation, and scalable processes. - Sound judgment. You make thoughtful decisions, especially when navigating ambiguity, risk, or sensitive situations. - Clear communication and influence. You explain complex topics in a way that’s easy to understand and can effectively guide decisions across a range of audiences. 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-sol