Head of Design and Research

Upside; Washington (District of Columbia); Hybrid; USD 249,000 - 263,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage starting on Day 1

Equity (ISOs)

401(k) program

Unlimited PTO

Flexible work environment

Learning and Development stipend

Lunch reimbursement for in-office employees

Job summary

Upside is seeking a Design Lead to enhance the consumer and payments experience. This hands-on role involves leading a small team while architecting design systems and frameworks across various platforms.

Ideal candidates will possess deep consumer product design experience, particularly in fintech or transaction-driven products. The position is based in Washington, DC, and offers a hybrid work model, with competitive compensation and benefits.

Upside is committed to diversity, providing an inclusive workplace for all.

Qualifications

• Deep consumer product design experience driving conversion and retention.
• Track record in scaling consumer apps during hypergrowth.
• Led design/research teams of 5-10 individuals.

Responsibilities

• Own quality and consistency across the consumer experience.
• Lead a team of designers and researchers.
• Architect cohesive design systems and frameworks.
• Partner with cross-functional teams for measurable outcomes.
• Deepen research practice integration into decision-making.

Skills

Consumer product design experience

Designing habit-forming systems

Experience in fintech or transaction-driven products

Strong systems-level product thinking

Analytical skills using data

Leadership experience with design teams

AI-centric approach to design

Effective in ambiguity

Job description

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.

The fine print:

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

• Amazing mission!

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].

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