Head of Design and Research at Upside

At Upside, we are changing the way brick-and-mortar commerce works by bringing the precision of online retail into the physical world. Our platform helps millions of users earn significant cashback while enabling local businesses to generate measurable, profitable growth. With billions of dollars in commerce flowing through our system annually, we are proud to support our retail partners, consumers, and sustainability initiatives. We are looking for a visionary leader to help us continue this momentum.

Role at a glance

We are seeking an executive-level Head of Design and Research to join our team on a full-time basis. This is a hybrid position, requiring you to work from our NYC or DC office two days per week. You will lead our design and research efforts, ensuring our products remain intuitive, powerful, and effective for both consumers and merchants.

Your impact

• Lead and inspire a diverse team of designers and researchers to uphold our design principles and vision.
• Partner closely with engineering, product, and marketing leadership to drive high-level strategy and innovative product execution.
• Refine our research practices and integrate deep user insights into our core decision-making processes.

What you'll need

We are looking for a seasoned leader who can navigate complex problem spaces and foster a culture of high-quality craft. You should have at least 10 years of professional design experience, including 5 or more years in a leadership role managing design and research teams. You must be comfortable scaling teams in both startup and established environments. We value candidates who can translate ambiguous challenges into clear, user-centric strategies and who possess the communication skills necessary to influence stakeholders across the organization.

Perks and compensation

The base salary range for this role is $216,000 to $270,000, plus potential bonuses and equity. We offer a comprehensive benefits package designed to support your well-being and professional growth:

• Medical, dental, and vision insurance starting on your first day.
• Equity compensation and a 401k program.
• Unlimited paid time off, plus federal holidays and an annual winter break.
• A dedicated learning budget to support your development.
• Flexible work arrangements with support for your home office.