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Upside
Washington, DC, United States; Chicago, IL, United States; New York, NY, United States; Austin, TX, United States
Source: Upside careers · View original posting
From Upside's posting. “We” and “our” refer to the employer.
We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit.
Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.
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.
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.
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.
This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.
LAYIQ is an independent job-discovery service. This listing does not imply a partnership with or endorsement by the employer. Review the original posting for current details and availability.
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