Head of Design and Research

Upside; Austin (TX); Hybrid; USD 249,000 - 263,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Equity (ISOs)

401(k) program

Unlimited PTO

Flexible work environment

Job summary

Upside is seeking a talented design lead in Austin to enhance its consumer and payments experience. This role involves leading a dedicated design team, architecting cohesive design systems, and driving measurable outcomes. Candidates should possess deep experience in consumer product design, scaling apps, and have a solid understanding of the analytics behind user experience.

The position offers a competitive salary, equity options, and an array of benefits from Day 1, creating a supportive and innovative work environment in Austin.

Qualifications

• Experience scaling a consumer app through hypergrowth (3M to 10M+ MAU).
• Understanding of UX impact through data-driven design.
• Track record of developing designs that drive conversion.

Responsibilities

• Lead a design team to enhance consumer and payments experience.
• Develop cohesive design systems across various platforms.
• Integrate design into product discovery processes.

Skills

Consumer product design experience

Designing habit-forming systems

Strong systems-level product thinking

Comfort in analytical environments

Leadership of design/research teams

AI-centric design approach

Bias to action in ambiguity

Job description

Meet Upside

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.

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 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.

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

Diversity And Inclusion

Diversity drives innovation, and our differences make us stronger. We’re 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 there's anything we can do to support a disability or special need during your application or interview process, please email [e-mail]. 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.

Compensation Range: $249K - $289K