Head of Design and Research

Upside • Washington, DC

20h • $249,000 - $289,000 • Hybrid

About The Position

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.

Requirements

• 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.

Responsibilities

• 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.

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!

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed