Head of Design and Research

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retailprofit measurement attribution and incrementalityto provide users with more value on their everyday purchases and brick-and-mortar businesses with new profitable customers. Weve 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 & Researchs 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.

• Deepen the research practice and its integration into decision-making.

• Apply an AI-native approach to how design and research scale.

• 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 510 and raised individual craft.

• AI-centric approach to design and research.

• Bias to action; effective in ambiguity without requiring a perfect environment.

Location: This hybrid role is based in our Austin Chicago DC or NYC -office attendance is required on Monday Tuesday and Thursday and may increase based on project-based needs and changes to Upsides in-office policy over time.

Compensation: The U.S. base salary range for this full-time position varies by work location:

• Tier 1: NYC $274000 $289000

• Tier 2: Austin Chicago Washington DC $249000 $263000

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!

Diversity and Inclusion:

Diversity drives innovation and our differences make us stronger. Were passionate about building a workplace that represents a variety of backgrounds skills and perspectives and we do not discriminate based on race religion color national origin gender sexual orientation age marital status veteran status or disability status. Everyone is welcome here!

If theres anything we can do to support a disability or special need during your application or interview process please email

This email is for accessibility accommodations only it should not be used to submit job applications.

Notice To Recruiters And Placement Agencies:

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.

Required Experience:

Director