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Remote, Oregon, United States
Remote only
Design Leadership, Hybrid IC/Manager
Cherry's providers are the business. They choose to offer Cherry, they use it every day, and their success directly determines ours. This role exists to make sure Cherry earns that relationship through great design, and to ensure the tools and experiences we give providers are best-in-class: clear, reliable, and built around how they actually work.
We're looking for a Senior Staff Product Designer who will contribute to the future of design across one of two pillars:
Core Experience is about the quality of the day-to-day product experience for providers: the apps, flows, and tools they use to run their practice with Cherry. This pillar is focused on raising the UX bar across the board, identifying the rough edges and systemic issues that erode provider trust, and driving the kind of experience improvements that make Cherry the product providers want to recommend to other practices. It also includes net new, zero-to-one products that expand the suite of value Cherry offers providers, growing what Cherry can do for the practices that depend on it.
Checkout Experience is about how Cherry shows up at the point of care, for both the provider and the patient. On the provider side, this means giving practices the right tools to offer Cherry financing in whatever form their business needs: embedded in their systems, at the front desk, through staff, or through new channels. On the patient side, it means ensuring that the people who access care through Cherry have an experience that's clear, trustworthy, and on their side: that they can understand their options, choose the right payment plan, complete a transaction without friction, and feel confident about how they're paying for care. The work is tied directly to volume, conversion, and the outcomes that let both practices and patients thrive.
You'll lead a small team of designers and stay close to the work yourself. Cherry's expectation is that leaders are makers. This is not a coordination role. We're in a period where design tools, AI workflows, and product processes are evolving fast, and we want our design leaders to be in that evolution directly, leading by example, not just setting direction from a distance.
Team Leadership
Manage and develop a small team of product designers, providing direction, feedback, and coaching
Contribute to the quality bar across your pillar through critique, direct collaboration, and high standards
Create space for designers to grow while staying close enough to the work to lead by example
Make it clear through your own output what great looks like
Core Experience or Checkout Experience
Contribute to experience strategy across your pillar, identifying the highest-leverage opportunities to improve provider outcomes
Drive design across the full range of surfaces your pillar touches, from the daily-use provider app to checkout flows and financing tools
Shape solution direction across initiatives and align Product, Engineering, and go-to-market teams around shared priorities
Craft & Execution
Contribute directly to design work alongside your team, not just in direction but in execution
Drive measurable improvements in experience quality, conversion, and provider satisfaction
Work at the intersection of strong product judgment and high visual and interaction craft
Balance short-term delivery with the longer-term systems thinking that compounds over time
Strategic Partnership
Partner closely with leadership to shape direction and prioritize investments
Work with Sales, Growth, and Ops to understand how providers experience Cherry in the real world
Communicate clearly across levels, from individual designers to executive stakeholders
8+ years of product design experience, with demonstrated ownership of complex product areas
Experience managing or developing designers, with genuine investment in the people you work with
Strong maker instincts: you contribute to design directly, not just by directing others
Systems thinking across workflows, platforms, and organizational boundaries
Sharp product judgment and comfort working in ambiguity, shaping problems before solutions are clear
Experience designing tools for operators, businesses, or professional users a plus
Strong cross-functional collaboration skills with Product, Engineering, Sales, and Ops
A track record of connecting design work to measurable business outcomes
You've managed a small design team but kept your hands in the work, because you wanted to, not because you had to
You care as much about the provider who uses Cherry fifty times a day as the one who signs up for the first time
You have strong opinions about experience quality and the credibility to hold the bar across a team
You're energized by the question of what great provider tooling looks like, not just what converts
You're comfortable in a fast-moving environment where the tools and processes you used last year may not be the ones you use this year
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 heart of the provider relationship.
