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Remote, Oregon, United States
Remote only
Cherry | Individual Contributor
The tools designers use are changing faster than at any point in the last two decades. AI is collapsing the gap between intent and implementation. Designers are shipping code. The traditional boundaries between design and engineering are dissolving, and that changes what a design system is, what it's for, and who it serves.
Cherry is building for that world now. We're looking for a Staff Design Engineer who doesn't just own our design system, but reimagines it: someone who sees this moment as an opportunity to define what design infrastructure looks like when AI is a first-class tool in every workflow.
This role is the foundation of Cherry's quality at scale. When the system is right, good decisions aren't made by individuals; they're encoded. Teams don't deliberate over spacing, motion, or component behavior. They use the system, and the right answers are already there.
Cherry's design system spans multiple products: our provider web application, consumer web application, provider mobile application, consumer mobile application, and point-of-sale system. You'll own the component library, the React codebase, interaction patterns, tokens, and documentation. Cherry is deeply committed to AI tooling. Everyone on the team is using Claude, and we have a dedicated AI Enablement team building internal tools to push that further. We're currently working in Figma and actively working to move away from it toward design tooling built for the AI era. This role will help lead that transition. This is not a role where you maintain a library. It's a role where you invent the next version of it.
Design System Ownership
Own the full design system: component library, React codebase, interaction patterns, tokens, and documentation
Write, ship, and maintain production React code with strong code hygiene, testing practices, and clear architecture
Define the interaction and visual design language for Cherry's component library: the standard every surface is held to
Building Quality at Scale
Encode quality standards into the system itself: components, tokens, and rules that make the right choice the easy choice
Work with AI tooling (Claude, Cursor, Codex) to embed design rules into development workflows, so quality guidance is available at the moment decisions are made
Partner with Cherry's AI Enablement team to build internal tools that extend the design system's reach
Cross-Team Partnership
Partner closely with our front-end engineering team in Turkey on component architecture, implementation, and code review
Serve the product design team as their primary design system partner, guiding usage and enabling confident contribution
Work with the broader engineering org to ensure components are easy to adopt, well-documented, and production-ready
Strategy & Vision
Own the strategy for how Cherry's design system evolves as AI becomes part of every designer's and engineer's workflow
Define the roadmap for components, pattern evolution, and process, with an eye toward what design systems look like in 2-3 years
Advocate for the long-term health of the system, balancing team requests with architectural integrity
5-8+ years of experience spanning product design and front-end engineering, with demonstrated strength in both
Deep proficiency in React, with strong opinions on component architecture, testing, and code quality
Expert-level skills in design tools, including component design, variants, tokens, and design system management
A sharp eye for visual and interaction design: spacing, motion, hierarchy, and the details that separate polished from almost-polished
Fluency with AI-assisted development tools like Claude Code, Cursor, or Codex
Experience building and maintaining a design system used by multiple teams in production
The ability to communicate across disciplines, fluent with designers, engineers, and product leaders alike
You're energized by AI tooling changing what design systems work actually means, and you want to be the person who figures out what it becomes
People can't quite decide if you're a designer or an engineer, and you've stopped trying to explain
You believe design systems are infrastructure: not a style guide, not a Storybook, but the thing that determines how fast and how well a company can build
You get frustrated when good design decisions aren't encoded somewhere they can scale, and you do something about it
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 builds the foundation that every product experience is made from.
