Senior Staff Product Designer

This is a fully remote position, open to applicants in United States.

📋 Description

• Take ownership of the quality of experiences across Cherry's consumer and provider interfaces, which include web applications, checkout processes, provider onboarding and acquisition pathways, the provider portal, and our interconnected rewards system.

• Personally lead design efforts on the most intricate and unclear challenges, especially in provider acquisition where clarity, persuasion, and conversion are essential.

• Create and uphold cohesive cross-experience journeys, minimizing friction between consumer-facing, provider-facing, and internal platforms.

• Establish and maintain quality standards through guidance, critique, and by setting an example through your own work.

• Serve as the main design collaborator with group-level Product leadership, jointly overseeing experience strategy and prioritization of the roadmap.

• Recognize design risks early, proactively modifying scope, sequencing, or staffing to prevent issues from escalating.

• Balance immediate execution demands with the need for long-term coherence and scalability in experience.

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

• Manage and mentor a small team of designers ranging from Senior to Staff level (up to three direct reports).

• Hire with intention, seeking designers who elevate the standard rather than simply filling roles.

• Provide coaching through practical experiences: design reviews, collaborative sessions, and direct feedback that fosters growth.

• Cultivate a team culture where high-quality craftsmanship is the norm rather than the exception.

⛳️ Requirements

• 6–10+ years of experience in product design, demonstrating ownership of complex, multi-surface products.

• Proven track record as a principal-level individual contributor: you have influenced product direction, not just executed it.

• Experience in managing a small team while maintaining a strong connection to hands-on design work.

• Strong systems thinking across comprehensive journeys and organizational boundaries.

• Extensive experience in designing acquisition, onboarding, or conversion-oriented processes.

• Excellent product judgment: knowing when to delve deeply, when to simplify, and when to decline requests.

• Comfort in navigating ambiguity and defining problems prior to developing solutions.

• Ability to communicate effectively with executives and cross-functional partners at all levels.

🏝️ Benefits

• Design Leadership

• Strategic Partnership

• Team Development