Staff Product Designer, AI Design Systems

Product Designer, AI Design Systems Cherry | Individual Contributor, Founding Design Systems Hire About the Role At Cherry, design and engineering aren't converging someday: they've already converged. We design with Claude. Our design system isn't a component library we maintain on the side; it's the infrastructure that makes speed and quality the same thing, for every one of our five products. We're looking for the founding member of Cherry's design systems team: someone who takes this system, still young, and turns it into the backbone of how Cherry builds. This isn't a caretaker role. It's a chance to define, from the ground up, what a design system looks like when AI is a first-class collaborator rather than an afterthought, and to lead that vision as the team grows around it. 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, and reinforced automatically by the tools everyone already uses to design and build. Get this right, and every team at Cherry moves faster with less risk. That's the bar this role is held to, not "good enough," but the standard every other decision gets measured against. Cherry's design system spans 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, end to end. Cherry is fully committed to AI-native workflows: everyone here designs and builds with Claude, and we have a dedicated AI Enablement team pushing that further. We're moving away from traditional Figma-first workflows toward tooling built for the AI era, and this role will lead that transition, not just adapt to it. You won't be maintaining a library. You'll be building, and leading, the next version of it, with real say in the team that grows around this work. What You'll Do Founding Member Serve as a founding member of Cherry's design systems team, with real say in how it's structured, staffed, and led as it grows Guide the team through the shift to AI-native workflows, and influence how Cherry adopts new tools and practices as they emerge Own the System Own the design system end to end: the component library, tokens, and documentation Own the design direction of the system, along with component architecture, implementation, and outcomes in code Improve the system across teams: identify structural issues, align approaches, and evolve patterns for scale rather than just maintaining what exists Lead on Design Influence interaction and visual design for the design system, guiding decisions across teams rather than owning a single surface Influence Cherry's design language, evolving it rather than just documenting what's already there Build for Claude First Build a Claude-first, modern AI design system: one where Claude and other AI agents produce on-system output by default Help determine what Cherry's design toolset looks like next, rather than defaulting to whatever we use today Collaborate Work closely with your front-end engineering partner in the USA on component architecture, implementation, and code review Improve how design and engineering communicate and execute together, identifying friction and adjusting process across initiatives What You Bring 6-10 years of experience in product design Real, proven coding and technical skills, not just familiarity with code A track record of guiding visual and interaction decisions across teams: evolving patterns and addressing inconsistencies, not just applying what already exists Experience improving a design system across teams: identifying structural issues, aligning approaches, and building for scale A strong point of view on design tooling: you'll help determine what Cherry's toolset looks like next, not just execute in Figma or Pencil because that's what we use today Ability to communicate fluently with designers, engineers, and product leaders, and to align multiple teams around a shared design direction The instinct to lead: you've either run a small team or function before, or you're ready to be the first person doing so Nice to Have Hands-on experience with Claude, including Claude Code: you've authored the skills and rules that encode design decisions into how it works, so it produces on-system output by default Comfortable writing and shipping production code: you don't need to be a React specialist, we already have a strong foundation for code quality Strong understanding of front-end testing practices and code hygiene Experience collaborating with distributed teams You're Probably a Great Fit If... You want to be the person who defines what design systems become in the AI era, not someone who waits to be told You believe design systems are the actual source of a company's scalability and efficiency: not a style guide, not a Storybook, but the infrastructure that determines how fast and how well a company builds You want to found something. This is a team of one today, and you'll have real say in what it becomes You get frustrated when good design decisions aren't encoded somewhere they can scale, and you do something about it 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 builds the foundation that every product experience is made from.