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Head of Design and Research



New York, NY, USA
Posted on Monday, April 22, 2024

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.

The Impact You'll Make:

The D&R teams are a diverse group of individuals who are unified by a common vision - Build first class user experiences for both our consumers and merchants to enable Upside's business. We are a small tightly knit team that has individuals embedded into engineering delivery teams. We work together across teams to maintain our design systems and principles and build amazing products.

  • Collaborate with engineering and product to enable key strategic initiatives
  • Manage a diverse team in establishing and maintaining Upside's Design Principles and Vision
  • Work with Research and Development leadership to improve and build the future of Upside
  • Incorporate systems thinking into Upside's Design System so that they are both modular and stand-alone full-featured product experiences that are both powerful and easy to use
  • Create a culture of craft, quality, and execution by inspiring, motivating, and leading product designers across experience levels
  • Work closely with our Product Management, Engineering, Marketing, and executive leadership to deliver best-in-class, innovative work
  • Own emergent, highly complex, and ambiguous opportunities from inception to a landed proposal. Frame opportunities, potential experience solutions, and drive initiative direction in partnership with research, prototyping, and product peers
  • Hone Upside’s research practice and deepen its integrations into our decision making mechanisms

What You Should Have:

  • You have 10+ years of professional design experience and 5+ years managing and leading design and research teams
  • You have brought a customer focus to high-impact, high-visibility projects.
  • You excel at written and verbal communication and use these skills to persuade and influence stakeholders toward building innovative products that uniquely resonate with customers
  • You work collaboratively with Engineering, Product, and Marketing team members to drive strategy and design execution
  • You have led, recruited, and scaled design teams at both startups and established companies
  • You have experience systematically growing product designer and researcher skills
  • Experience using UX to influence strategic decision making, communicate strategic concepts, and facilitate understanding
  • Experience translating ambiguous asks and directions into clear user centric approaches
  • Experience fostering divergent design thinking and shepherding radical ideas that can truly evolve products
  • Experience with organizational transformation and design education to foster team growth
  • Provide consultation of key team-level research, insights, and product strategy to drive quality and cohesion.
  • Set the standard and foster a culture for UX design practice not only as a means to delivering solutions, but as a way of deepening understanding and driving strategic conversations in a complex problem space


This hybrid role is required to work at our NYC or DC office for 2 days/week.


The US base salary range for this full-time position is $216,000-$290,000 + potential bonus + equity + benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range during the hiring process.


  • Medical, dental, and vision coverage starting on Day 1
  • Equity (ISOs)
  • 401(k) program
  • Family planning programs + generous paid parental leave
  • Physical fitness and wellness memberships
  • Emotional and mental health support programs
  • Unlimited PTO + 10 federal holidays + our annual, week-long Winter Break
  • Flexible work environment + support for your home office setup
  • Lunch and parking reimbursement for in-office employees
  • Employee Resource Groups
  • Learning and Development opportunities
  • Transparent culture
  • Amazing mission!

Why Join Upside?

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, was named a Top Workplace for Perks & Culture by The Muse, and was listed second year in a row on the Deloitte Fast 500.

At Upside, we believe that diversity drives innovation. Our differences are what 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!

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.