Head of Design and Research

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 ROLE Upside is in Phase II — scaling toward 10M MAU, ~175K retail locations, and billions in payments GMV. Design & Research's mandate is narrow and clear: raise the consistency and polish bar across the entire consumer and payments experience, moving the product from "functional" to "flawless" and embedding design into early discovery. This is a hands-on craft-and-scale leadership role for a small, embedded team. It is not a greenfield visionary role or a large-org-building role. WHAT YOU'LL DO: - Own the quality, consistency, and polish bar across the consumer and payments experience. - Lead a small, tightly knit team of designers and researchers embedded in delivery pods; systematically grow their craft and how the team operates. - Architect cohesive design systems and frameworks across fragmented journeys and surfaces — balancing design integrity against iteration speed. - Partner with Product, Engineering, and Marketing to pull design into discovery and drive measurable outcomes across onboarding, discovery, redemption, and retention. - Deepen the research practice and its integration into decision-making. - Apply an AI-native approach to how design and research scale. WHAT YOU'LL NEED: - Deep consumer product design experience where trust, credibility, and onboarding psychology drive conversion and retention — ideally fintech, marketplaces, or transaction-driven products. - Track record designing habit-forming systems (frequency, retention, cross-category adoption) at consumer scale. - Has personally helped scale a consumer app through hypergrowth (~3M → 10M+ MAU). - Strong systems-level product thinking; sound judgment on where consistency matters vs. where to move fast. - Comfort in highly analytical environments; uses data to drive and prove UX impact. - Has led design/research teams of ~5–10 and raised individual craft. - AI-centric approach to design and research. - Bias to action; effective in ambiguity without requiring a perfect environment. THE FINE PRINT: Location: This hybrid role is based in our Austin, Chicago, DC, or NYC office. In-office attendance is required on Monday, Tuesday, and Thursday and may increase based on project-based needs and changes to Upside’s in-office policy over time. Compensation: The U.S. base salary range for this full-time position varies by work location: - Tier 1: NYC $274,000 – $289,000 - Tier 2: Austin, Chicago, Washington, DC $249,000 – $263,000 In addition to base salary, this position is also eligible for equity and 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 for your location during the hiring process. Benefits: - Medical, dental, and vision coverage starting on Day 1 - Equity (ISOs) - 401(k) program - Family planning programs + paid parental leave - Physical fitness and wellness memberships - Emotional and mental health support programs - Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break - Flexible work environment - Lunch reimbursement for in-office employees - Employee Resource Groups - Learning and Development stipend - Transparent culture - Amazing mission! Diversity and Inclusion: Diversity drives innovation, an