Head of Design and Research

DC, Remote. Posted 5 months ago

The role

The Head of Design and Research will own the quality, consistency, and polish bar across the consumer and payments experience. This leader will manage a small team of designers and researchers to architect design systems and integrate research into decision-making.

What you will do

Own the quality, consistency, and polish bar across the consumer and payments experience
Lead a small team of designers and researchers embedded in delivery pods
Architect cohesive design systems and frameworks
Partner with Product, Engineering, and Marketing to drive 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

Required qualifications

Deep consumer product design experience where trust, credibility, and onboarding psychology drive conversion and retention
Track record designing habit-forming systems at consumer scale
Has personally helped scale a consumer app through hypergrowth (~3M → 10M+ MAU)
Strong systems-level product thinking
Comfort in highly analytical environments; uses data to drive and prove UX impact
Has led design/research teams of ~5–10
AI-centric approach to design and research
Bias to action; effective in ambiguity

Nice to have

ideally fintech, marketplaces, or transaction-driven products

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

About the company

Upside created technology to transform brick-and-mortar commerce using profit measurement, attribution, and incrementality. The platform helps users earn cashback and helps businesses earn measurable profit.