# Head of Design and Research at Upside

- Company: Upside
- What the company does: Earn every time you shop gas, grocery, or food with Upside's free top-rated app. Get cash back on everyday necessities, making your purchases more rewarding. Download and start earning today! Backed by Bessemer and General Catalyst.
- Company website: https://www.upside.com/
- Type: Startups
- Level: Principal and up
- Location: DC
- Work setup: Remote
- Pay: $249K to $289K base salary per year (USD)
- Posted: 2026-06-17
- Apply by: 2026-10-08
- Apply: https://jobs.ashbyhq.com/upside/a1c24db0-78fe-4a35-bc01-1052444f91cc
- Page: https://www.1752.vc/careers/jobs/upside-head-of-design-and-research/

## About 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 they're looking for

- 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

Tags: Design and Research