Senior Staff Product Designer

Cherry

Senior Staff Product Designer leading design quality and experience coherence across Cherry's product ecosystem. Engaging directly with Product and Engineering leadership while managing a small team.

Posted 6/22/2026full-timeRemote • 🇺🇸 United StatesSeniorWebsite

About the role

Key responsibilities & impact

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
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
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

Requirements

What you’ll need

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.

Benefits

Comp & perks

Design Leadership
Strategic Partnership
Team Development

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

product designuser experience designdesign systemsacquisition flowsonboarding flowsconversion designcross-experience journeysdesign critiqueteam managementsystems thinking

Soft Skills

leadershipcommunicationinfluencecoachingproblem-solvingstrategic thinkingcollaborationpersuasionadaptabilitycreativity