About the RoleWe'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.
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Benefits:- Medical, dental, and vision coverage starting on Day 1
- 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!
