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.

About the job:

As our first Total Rewards Director, you’ll be responsible for evaluating, creating, and implementing the day-to-day operations of all employee compensation-related and benefits programs (such as equity, health, dental, vision, short-term disability, life insurance, accident plan, flexible spending plan, etc.). You’ll research current and upcoming competitive markets for employee, executive pay, and benefits to continue to ensure that our pay rates are fair and equitable in order to attract and retain top talent. If you have a passion for total rewards, compensation, and benefits and have built a Total Rewards function in both private and public company environments, this opportunity may be the right fit for you!

What you’ll do:

You’ll use your 10+ years of experience in both benefits and compensation, preferably within high tech or SaaS to:

• Develop and implement Upside’s Global Total Rewards philosophy and strategy that include: programs, compensation, equity, global mobility, benefits, and leave and wellness programs.
• Deliver the total rewards “story” through the appropriate communication vehicles so our people understand the value of the program, their benefits and how they operate, and all available resources.
• Establish a benefits methodology and subsequent benefits programs inclusive for all employees that can scale, are cost-effective and competitive.
• Own the transition from a PEO to bringing benefits and a 401(k) program in-house.
• Oversee the annual benefit plan renewal activities and the open enrollment process through managing the company’s communication approach and materials for employees.
• Develop organizational training and feedback sessions to ensure our people have the right level of understanding of our philosophies and programs, while allowing for the opportunity to provide input to our approach.
• Ensure the company follows all compensation and benefits laws and regulations at the federal and state levels.
• Advise on marketplace trends and relevant laws to support current programs and future areas of investment

What you need:

• 10+ years of experience in total rewards, compensation, and benefits
• Experience building large-scale reward or recognition programs from the ground up, ideally at a technology start-up
• Experience with equity programs in both a private and public company environment.
• Global benefit experience includes health and welfare plans, leave management, time off practices, and retirement plans.
• Experience in high-growth environments with the ability to handle shifting priorities and multitask in a loose-structure, high-expectation environment.
• The ability to be flexible and creative, comfortable with ambiguity, organized, and detail-oriented.
• A clear communication style so that you’re able to bridge a big picture vision and a tactical plan that our employees understand at the lowest level of detail
• An analytical approach, as this role must demonstrate strong analytical and creative problem-solving skills, including statistical analysis and modeling.
• A deep commitment to customer service and empathy

The fine print:

• 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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