Head of Design and Research

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.

• 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.