Head of Design & Research — AI-Driven Scale Leader

Upside; Illinois; Hybrid; USD 249,000 - 263,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Equity (ISOs)

401(k) program

Flexible work environment

Unlimited PTO + 10 paid federal holidays

Learning and Development stipend

Job summary

Upside is looking for a design leader to enhance the consumer and payments experience as part of a hybrid role based in Chicago, Austin, DC, or NYC. This position requires a hands-on approach to scale product quality while leading a team of designers in delivering a polished user experience.

The ideal candidate will demonstrate extensive experience in consumer product design, especially in fintech or transaction-driven markets. The role demands strong leadership skills to cultivate design systems and partner cross-functionally with product and engineering teams.

Qualifications

• Deep consumer product design experience required.
• Track record designing habit-forming systems needed.
• Experience scaling a consumer app through hypergrowth is essential.

Responsibilities

• Own the quality and consistency across consumer experiences.
• Lead a small team of designers and researchers.
• Architect design systems and frameworks.

Skills

Consumer product design experience

Designing habit-forming systems

Strong systems-level product thinking

Analytical environment comfort

AI-centric design approach

Job description

Upside is looking for a design leader to enhance the consumer and payments experience as part of a hybrid role based in Chicago, Austin, DC, or NYC. This position requires a hands-on approach to scale product quality while leading a team of designers in delivering a polished user experience.

The ideal candidate will demonstrate extensive experience in consumer product design, especially in fintech or transaction-driven markets. The role demands strong leadership skills to cultivate design systems and partner cross-functionally with product and engineering teams.