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!

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

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
• Able 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)

Qualifications

• CPP, CEBS, or similar certifications are a plus

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

What You Bring

• Consistent delivery with measurable impact
• Effective stakeholder partnership
• Operational discipline
• Sound judgment and discretion
• Clear communication and influence

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.

Benefits

• Medical, dental, and vision coverage starting on Day 1
• Equity (ISOs)
• 401(k) program
• Familial 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
• Awesome mission!