Payroll and Benefits Lead, Upside
$153-183k
+ Equity
More information about location
3 days a week in office
Mobile reward application for retail spending
Be an early applicant
Mobile reward application for retail spending
201-500 employees
Be an early applicant
$153-183k
+ Equity
More information about location
3 days a week in office
201-500 employees
Company mission
To advance the economic power of people living and working in the real world.
Role
Who you are
- 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
What the job involves
- 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
- 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
- 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
- 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
Our take
Loyalty systems, vouchers, and other special offers have a proven track record at winning over new customers for businesses. However, customers can be reluctant to sign up due to the sheer number of these schemes. Upside exists to unify these loyalty schemes with a single flexible reward app.
While retail reward platforms are nothing new, Upside functions more like a marketplace, linking participating businesses to potential customers. It also rewards customers with cash back on eligible purchases, a more flexible reward than is traditional in loyalty schemes.
With over 50,000 businesses enrolled and 30 million app users, Upside has grown into a major player in this sector. The company is well-funded and ever-expanding its offering, with a product that is increasingly appreciated by consumers in an expensive world, as well as the businesses who depend on their custom.
Freddie
Company Specialist at Welcome to the Jungle
Insights
24% employee growth in 12 months
Company
Funding (1 round)
Apr 2022
$65m
SERIES D
Total funding: $65m
Company benefits
- Health and Wellness - We’re happy to provide our team members with generous health, vision, and dental insurance options
- Lunch - We cover the cost of lunch everyday for team members onsite to enhance our team building and encourage collaboration. Plus local restaurants appreciate it!
- Stock Options - Our team’s success is our company’s success, and we should all have a stake in that. We’re glad to offer our team members valuable stock options
- Unlimited PTO - Yes, you read that right. When you need time off, we’ve got you covered
Company HQ
Dupont Circle, Washington, DC
Leadership
Alex Kinnier
(CEO & Co-Founder)Experience as Group Product Manager for Google from 2005 to 2008. Senior Vice President of Products and Engineering for Opower from 2012 to 2015.
Wayne Lin
(CPO & Co-Founder)Experience as Product Manager for Google from 2005 to 2010. Vice President of Product Management & Analytics for Opower from 2010 to 2015.
Rick McPhee
(Co-Founder)Experience as Vice President of Engineering for HP's Fortify Software from 2008 to 2012. Senior Vice President of Engineering for Opower from 2012 to 2015.
Joanna Kochaniak
(Engineer & Co-Founder)Experience as Programmer Analyst for the Institute for Physical Sciences from 2007 to 2010. Lead Software Engineer for Opower from 2010 to 2015.
Jan Rubio
(Designer & Co-Founder)Experience as Research Assistant for George Washington University from 2009 to 2011. Senior Software Engineer for Opower from 2011 to 2016.
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