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 cash back than any other product, and hundreds of thousands of brick and mortar businesses earn measurable profit. Billions of dollars in commerce runs through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and towards important sustainability initiatives. Our mission, values, and dedication to inclusivity guide our team of more than 300 people worldwide, and the quality of our culture is reflected in the impact we’ve had on the people and businesses we work with. 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:

• Manage benefit administration lifecycle of all health and welfare plans from newly enrolling in benefits, employee changes, to termination.
• 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, including communication, employee education and support.
• 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.
• Lead compliance requirements for all benefit plans by working closely with external auditors, consultants, and legal counsel to ensure accurate and timely reporting of benefits-related information.
• Manage leave-of-absence program including, medical, disability, and applicable leaves of absence, including familiarity with FMLA and other state paid leaves, including coordination of 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:

• 5+ years' progressive benefits experience in a multi-state environment, consumer tech benefits a plus.
• Experience in a fast-paced company with a vision to create scalable programs.
• 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 strong attention to detail.
• A bachelor's degree is required.

The fine print:

• Location: This is a hybrid role and is required to work from our DC, NYC, Austin, or Chicago office 2 days/week.
• 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!

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