Benefits & Payroll Lead

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‑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 Location This hybrid role can be based in either our DC or NYC office. In‑office attendance is required on Monday, Tuesday, and Thursday, and may increase based on project‑based needs and changes to Upside’s in‑office policy over time. Compensation The U.S. base salary range for this full‑time position is $153,000 – $183,000 + equity + benefits. The final starting pay will be determined based on work location, job‑related skills, experience, qualifications, and market conditions. Your recruiter can share more about the specific salary range during the hiring process. Benefits Medical, dental, and vision coverage starting on Day1 Equity (ISOs) 401(k) program Family planning programs + paid parental leave Physical fitness and wellness memberships Emotional and mental health support programs Unlimited PTO + 10 paid federal holidays + our annual, week‑long Winter Break Flexible work environment Lunch reimbursement for in‑office employees Employee Resource Groups Learning and Development stipend Transparent culture Amazing mission! Diversity and Inclusion Diversity drives innovation, and our differences make us stronger. We’re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here! Disability Accommodations If there's anything we can do to support a disability or special need during your application or interview process, please email View email address on click.appcast.io. This email is for accessibility accommodations only and should not be used to submit job applications. #J-18808-Ljbffr Upside Services