Benefits Manager

Meet Upside

We created Upside to help communities thrive! Our retail 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 cash back than any other product, and tens 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 local retailers, the consumers they serve, and towards important sustainability initiatives. 

Upside was named on Deloitte's 2021 & 2022 list of Fastest Growing 500 Tech Companies and  #308 in Inc.’s America’s fastest growing private companies of 2022. Upside’s Series D funding round was led by General Catalyst with a $1.5 billion valuation in March 2022. Other notable investors include Bessemer Ventures and Formation8.

Our mission, values, and commitment to inclusivity guide our team of more than 350 people worldwide, and the quality of our culture is reflected in the impact we’ve had on communities nationwide. But don’t just take our word for it! In 2023, Upside was included as a Top Workplace in the USA, received six Best Places to Work awards from Built In, and was named a Top Workplace for Perks & Culture by The Muse.

What you’ll do:

• Lead the analysis of benefits programs based on market research and benchmarking to evaluate the competitiveness of plan offerings.
• Provide recommendations for plan design changes based on benefits claim data, plan competitiveness, and company’s goal of improving the physical, mental, and financial health of employees across the organization.
• Work collaboratively across the People Team to develop and implement effective communication and change management plans that enhance the employee experience and perceived value of our programs.
• Lead the annual benefits open enrollment process including communication and employee education.
• Manage relationships with benefits vendors, brokers, and consultants to monitor service levels, and evaluate program effectiveness.
• Maintain benefit election information in HRIS and Payroll platforms and ensure accuracy with carriers.
• Conduct new employee orientation to better educate employees on benefit plan offerings. 
• Drive the strategy and implement comprehensive Wellness Programs across the company.
• Work closely with external auditors, consultants, and legal counsel to ensure accurate and timely reporting of benefits-related information.
• Work closely with HRBPs and employees to administer all leave-of-absence requests and disability paperwork: medical, personal, disability and applicable leaves of absence and coordinates with health benefits.
• Reconcile invoices and ensure timely payment of premiums for all benefit plans.
• Conduct regular reconciliations and audits of employee benefit records to ensure accuracy and compliance with legal requirements.

What you need:

• 8+ years' progressive benefits experience in a multi-state environment, international benefits a plus.
• 3+ years of experience in a strategic benefits role.
• Experience in a fast-paced company with a vision to create scalable programs
• Strategic background to bring the Benefits department and role to the next level while leveraging technology solutions that not only improve efficiency but also create an improved experience for employees.
• Outstanding communication, presentation, interpersonal skills, ethics, and cultural awareness.
• Comprehensive understanding of benefits and all state and federal regulations associated.
• Proven ability to manage multiple tasks, show adaptability and meet deadlines while maintaining accuracy with a strong attention to detail.
• Bachelor's degree in Human Resources, Accounting or Business, or related field; SHRM and or CEBS certificate a plus.

The fine print:

• Location: This is a fully-remote role that may sit anywhere in the United States. You're welcome to work from our DC, Austin, Chicago or New York office if you're in-region!
• 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.

At Upside, we believe that diversity drives innovation. Our differences are what makes us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives and do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here. Come join us!