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-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 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!

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! If there's anything we can do to support a disability or special need during your application or interview process, please email accommodations@upside.com. This email is for accessibility accommodations only, it should not be used to submit job applications.

Notice To Recruiters And Placement Agencies

This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.