The roleUpside 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!
