Senior Staff Product Designer

Design Leadership, Hybrid IC/Manager

About the Role

Cherry is looking for a Senior Staff Product Designer to lead design quality and experience coherence across our full product ecosystem. This is a rare role: roughly 70% hands-on design leadership, 30% people management. You'll be the most senior designer embedded in our Experience group, partnering directly with Product and Engineering leadership while staying close to the work that matters most.

You won't be managing from a distance. You'll be in the details, shaping provider acquisition flows, connecting consumer and provider journeys, and raising the bar on craft across every surface. You'll also manage a small team of Senior and Staff designers (up to three), coaching them, hiring alongside them, and holding the standard for what good looks like at Cherry.

We're building across a wide surface area: consumer and provider web apps, mobile and iPad experiences, a point-of-sale system, and a growing design system that ties it all together. The person in this role will have a point of view on how these experiences connect and the judgment to know where to go deep and where to let the team run.

This is a role for someone who is a designer first. Someone who's led work at a principal or staff level, and who's picked up management not because they wanted a title, but because they wanted to make the people around them better.

What You'll Do

Design Leadership

• Own experience quality across Cherry's consumer and provider surfaces, including web applications, checkout flows, provider onboarding and acquisition funnels, the provider portal, and our connected rewards ecosystem

• Lead design personally on the most complex and ambiguous problems, particularly in provider acquisition where clarity, persuasion, and conversion are critical

• Design and maintain cohesive cross-experience journeys, reducing friction between consumer-facing, provider-facing, and internal surfaces

• Set and enforce quality standards through direction, critique, and your own example

Strategic Partnership

• Act as the primary design partner to group-level Product leadership, co-owning experience strategy and roadmap prioritization

• Identify design risk early, proactively adjusting scope, sequencing, or staffing before problems compound

• Balance short-term execution needs with longer-term experience coherence and scalability

• Influence decisions across Product, Engineering, Sales, and Marketing without relying on formal authority

Team Development

• Manage and develop a small team of Senior to Staff-level designers (up to three reports)

• Hire thoughtfully, finding designers who raise the ceiling, not just fill seats

• Coach through real work: design reviews, pairing sessions, and direct feedback that moves people forward

• Build a team culture where craft is the expectation, not the exception

What You Bring

• 6–10+ years of product design experience with demonstrated ownership of complex, multi-surface products

• A track record of operating as a principal-level individual contributor: you've shaped product direction, not just executed on it

• Experience managing a small team without losing your connection to the craft

• Strong systems thinking across end-to-end journeys and organizational boundaries

• Deep experience designing acquisition, onboarding, or conversion-focused flows

• Sharp product judgment: knowing when to go deep, when to simplify, and when to say no

• Comfort working in ambiguity and shaping problems before solutions exist

• The ability to communicate clearly with executives and cross-functional partners at every level

You're Probably a Great Fit If...

• You've spent most of your career as an IC and you're protective of that, but you've stepped into leadership because you care about the people and the quality around you

• You've worked at early-stage or high-growth companies where you had to build the design culture, not just inherit it

• You have a portfolio that shows range: consumer flows, complex multi-step systems, design systems work, and the occasional zero-to-one bet

• People you've managed would say you made them meaningfully better at their craft

About Cherry

Cherry is a patient financing platform that connects consumers with healthcare providers, making care more accessible and practice growth more achievable. Our product spans consumer-facing payment experiences, provider-facing business tools, and the infrastructure that ties them together. Design at Cherry is not a service function, it's a strategic lever, and this role sits at the center of it.