Staff Product Designer, AI Design Systems

📍 Job Overview

Job Title: Staff Product Designer, AI Design Systems

Company: Cherry Technologies, Inc.

Location: United States

Job Type: Full-time

Category: Design Systems / Product Design

Date Posted: 2026-09-04

Experience Level: 6-10 years

Remote Status: Fully Remote

🚀 Role Summary

• Lead the foundational development of an AI-native design system, shaping the future of design and engineering workflows at Cherry.

• Own the end-to-end design system lifecycle, including component library, interaction patterns, tokens, and comprehensive documentation.

• Drive the strategic shift towards AI-integrated design tooling, moving beyond traditional Figma-centric approaches.

• Collaborate closely with front-end engineering partners to ensure robust component architecture, implementation, and code quality.

📝 Enhancement Note: This role is identified as a "Founding Design Systems Hire" and "Individual Contributor," indicating a high degree of autonomy and strategic influence. The emphasis on AI-native workflows and a shift away from traditional tooling suggests a forward-thinking approach to design operations and product development.

📈 Primary Responsibilities

• Serve as the inaugural member of Cherry's design systems team, with significant influence on its future structure, staffing, and leadership.

• Define and champion AI-native design workflows, guiding the adoption of new tools and practices for the entire organization.

• Take full ownership of the design system, encompassing the component library, design tokens, and all associated documentation.

• Architect and implement interaction patterns and visual design standards that evolve the company's design language at scale.

• Proactively identify structural issues within the design system, aligning disparate approaches and developing patterns that support long-term scalability.

• Collaborate directly with a US-based front-end engineering partner on component architecture, code implementation, and conducting code reviews to maintain high standards.

• Enhance communication and execution efficiency between design and engineering teams by identifying and mitigating process friction.

• Drive the development of a design system built for AI agents like Claude, ensuring on-system output by default.

• Influence the evolution of Cherry's design toolset, actively participating in decisions about future tooling beyond current industry standards.

📝 Enhancement Note: The responsibilities highlight a transitionary period for the company's design operations, moving towards AI-driven processes and a robust, scalable design system infrastructure. The expectation to "lead" and "define" signifies a strategic, not just tactical, component to this role.

🎓 Skills & Qualifications

Education: Not explicitly specified, but a strong foundation in design principles and technical understanding is implied.

Experience: 6-10 years of progressive experience in product design, with a focus on design systems and technical implementation.

Required Skills:

• 6-10 years of hands-on product design experience.

• Proven coding and technical skills, demonstrating a deep understanding of front-end development principles and implementation.

• Demonstrated ability to guide visual and interaction design decisions across multiple teams, evolving patterns and addressing inconsistencies.

• Experience in improving and scaling design systems across various product teams.

• Strong point of view on design tooling, with the ability to influence and shape future toolset adoption.

• Excellent communication skills, enabling effective collaboration with designers, engineers, and product leaders.

• Demonstrated leadership potential or prior experience leading a small team or function.

• Proficiency in developing and maintaining component libraries, design tokens, and comprehensive documentation.

• Experience in identifying structural issues within design systems and implementing solutions for scale. Preferred Skills:

• Hands-on experience with AI agents like Claude, specifically authoring rules that embed design decisions into AI output.

• Comfort and proven ability to write and ship production code; while not requiring React specialization, familiarity is advantageous.

• Strong understanding of front-end testing practices and code hygiene principles.

• Experience collaborating effectively with distributed or remote teams.

• Familiarity with modern design tooling beyond traditional Figma workflows.

📝 Enhancement Note: The requirement for "real, proven coding and technical skills" and "ability to communicate fluently with designers, engineers, and product leaders" suggests this role bridges the gap between pure design and front-end development, with a strong emphasis on technical execution and cross-functional influence. The "Nice to Have" section points towards a strong preference for candidates already familiar with AI-driven design workflows.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate end-to-end ownership of a design system, showcasing its evolution and impact across multiple products or teams.

• Provide clear examples of how you have improved a design system's architecture, component library, or token system for scalability and efficiency.

• Showcase your technical capabilities through code samples or descriptions of implemented components, highlighting your collaboration with engineering.

• Present case studies that illustrate your strategic thinking in design tooling and your approach to AI-native workflows. Process Documentation:

• Detailed documentation of your approach to designing and implementing scalable component libraries, including interaction patterns and visual design guidelines.

• Examples of how you have documented design tokens and their application across various platforms and contexts.

• Case studies that outline your process for identifying and rectifying structural issues within a design system to improve maintainability and developer experience.

• Evidence of your process for fostering collaboration between design and engineering, including contributions to code review and process improvement initiatives.

📝 Enhancement Note: Given the emphasis on "founding" this team and driving AI-native workflows, a portfolio that clearly articulates strategic vision, technical execution, and a forward-thinking approach to design systems will be crucial. The ability to demonstrate impact beyond just UI design, focusing on infrastructure and scalability, will be key.

💵 Compensation & Benefits

Salary Range: Based on the experience level (6-10 years), the "Staff" title, and the fully remote nature within the United States, a competitive salary range for a Product Designer specializing in AI Design Systems would typically fall between $150,000 - $200,000 USD per year. This estimate is derived from industry benchmarks for senior/staff-level design roles in tech companies operating remotely in the US, considering the specialized nature of AI and design systems.

Benefits:

• Comprehensive health, dental, and vision insurance.

• Stock options or equity, reflecting the founding hire status and potential for company growth.

• Generous paid time off (PTO) and holidays.

• Professional development budget for conferences, courses, and learning resources related to AI and design systems.

• Remote work stipend for home office setup and ongoing expenses.

• 401(k) retirement plan with company match.

• Opportunities for significant impact and leadership growth as the design systems team expands.

Working Hours: 40 hours per week, with flexibility to accommodate remote collaboration across different time zones within the United States.

📝 Enhancement Note: The salary range is an estimate based on industry standards for a Staff-level Product Designer in the US tech sector with specialized skills in AI and Design Systems. The "founding hire" aspect suggests potential for equity, which can significantly increase overall compensation.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology / Patient Financing. Cherry Technologies operates in the FinTech and HealthTech sectors, providing a patient financing platform that enhances healthcare accessibility and supports practice growth.

Company Size: The description implies a growing startup environment where this role is a foundational hire for the design systems team, suggesting a company that is scaling rapidly. The "founding member" status for design systems indicates the team is likely small but poised for expansion.

Founded: While not explicitly stated, the emphasis on building foundational infrastructure and a "young" design system suggests a company that is past its initial startup phase and is now focusing on scaling operations and product quality.

Team Structure:

• The design systems team is currently a team of one (this role) but is intended to grow, with the individual having significant say in its future composition and leadership.

• This role will collaborate closely with front-end engineering partners, implying a strong design-engineering partnership model.

• Cross-functional collaboration will be essential, working with product leaders and other design teams across multiple products (provider web, consumer web, provider mobile, consumer mobile, POS). Methodology:

• AI-Native Workflows: A core methodology is the integration of AI (specifically Claude) as a first-class collaborator in design and engineering processes. This involves moving beyond traditional Figma-first approaches to tooling built for AI.

• Design Systems as Infrastructure: The company views design systems not just as component libraries but as the fundamental infrastructure for scalability and efficiency in building products.

• Data-Driven Design Evolution: While not explicitly stated, the emphasis on improving systems and aligning approaches suggests a data-informed approach to identifying issues and evolving the design system based on usage and impact.

Company Website: https://withcherry.com/

📝 Enhancement Note: The company's focus on AI-native workflows and leveraging design systems as infrastructure indicates a modern, forward-thinking approach to product development. The "founding hire" status for this role means the individual will have a substantial impact on shaping these methodologies.

📈 Career & Growth Analysis

Operations Career Level: This role is at the "Staff" level, indicating a senior individual contributor position. It signifies a high degree of autonomy, strategic influence, and expertise. The role is expected to not only execute but also to define processes, influence direction, and potentially lead future team growth.

Reporting Structure: While not explicitly detailed, as a founding member and individual contributor, this role likely reports to a Head of Design, Director of Product, or CTO. The emphasis on "real say in how it's structured, staffed, and led" suggests a high degree of autonomy in defining its own reporting and team structure as it grows.

Operations Impact: The impact of this role is described as foundational to Cherry's quality and scalability. By establishing a robust, AI-integrated design system, this individual will directly influence:

• Speed of Development: Enabling faster iteration and product launches.

• Product Consistency & Quality: Ensuring a cohesive user experience across all five products.

• Efficiency: Reducing redundant design and development efforts.

• Innovation: Facilitating the adoption of new AI-driven design and development paradigms.

Growth Opportunities:

• Leadership Development: Opportunity to build and lead the design systems team, defining its mission, hiring strategy, and operational processes.

• Technical Specialization: Deepen expertise in AI-native design workflows, advanced component architecture, and modern front-end development practices.

• Strategic Influence: Shape the future of design and engineering tooling and methodologies at Cherry, impacting company-wide product development.

• Career Advancement: Potential to grow into a Design Systems Lead or Manager role as the team expands.

📝 Enhancement Note: The "Staff" designation, coupled with the "founding hire" context, positions this role as a significant growth opportunity for an individual contributor looking to establish and lead a critical function within a scaling tech company. The emphasis on AI integration offers a unique path for specialization.

🌐 Work Environment

Office Type: Fully Remote. The role is designated as "TELECOMMUTE" with the location requirement being "United States." This indicates a commitment to a distributed workforce.

Office Location(s): United States. Candidates must be based within the United States to be considered.

Workspace Context:

• Collaborative Environment: While remote, the role emphasizes close collaboration with a US-based front-end engineering partner and product leaders. Expect regular virtual meetings, asynchronous communication, and shared digital workspaces.

• Tooling & Technology: Access to modern design and development tools is expected, with a specific focus on evolving towards AI-native tools and away from traditional Figma-centric workflows. This implies an environment that embraces experimentation with new technologies.

• Team Interaction: Opportunities for interaction will be through virtual channels, including Slack, video conferencing, and collaborative design/coding platforms. The remote setup necessitates proactive communication and engagement.

Work Schedule: Standard 40-hour work week is expected. Flexibility may be available, but alignment with core US business hours for collaboration with engineering and product teams will be important.

📝 Enhancement Note: The fully remote nature necessitates strong self-discipline, proactive communication, and comfort with asynchronous collaboration. The company's commitment to AI suggests a dynamic and evolving technological landscape within the remote work environment.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess experience in product design, design systems, technical skills, and leadership potential.

• Portfolio Presentation & Discussion: A deep dive into the candidate's portfolio, focusing on design system experience, technical contributions, leadership initiatives, and vision for AI-native design. Expect to discuss specific case studies related to scalability, process improvement, and cross-functional collaboration.

• Technical/Design Challenge: Potentially a take-home assignment or live coding/design exercise focused on component architecture, system thinking, or AI integration concepts.

• Cross-functional Interviews: Meetings with engineering partners and product leaders to assess collaboration style, communication skills, and strategic alignment.

• Final Interview: Discussion with senior leadership to evaluate overall fit, leadership aspirations, and strategic vision for the design systems function.

Portfolio Review Tips:

• Highlight Design System Ownership: Clearly showcase your end-to-end experience with design systems, from initial concept to ongoing maintenance and evolution.

• Demonstrate Technical Depth: Include examples of implemented components, architectural decisions, or contributions to codebases. If possible, provide links to live implementations or code repositories.

• Showcase AI Integration: If you have experience with AI in design or development, make this a prominent part of your portfolio. Articulate your thought process and the outcomes.

• Quantify Impact: Use metrics to demonstrate the impact of your design system work (e.g., reduction in design/dev time, increase in consistency, adoption rates).

• Articulate Vision: Clearly communicate your strategic vision for the future of design systems, especially in the context of AI, and how you would approach building and leading this function at Cherry.

• Focus on Leadership: Provide examples of how you have influenced design direction, guided teams, or taken initiative to drive change.

Challenge Preparation:

• AI Design System Concepts: Be prepared to discuss how AI (like Claude) can be integrated into design system workflows, from generation to governance.

• Scalability and Architecture: Understand principles of building scalable component libraries and design token systems.

• Design-Engineering Collaboration: Think about strategies for improving communication and efficiency between these two functions.

• Tooling Evolution: Be ready to articulate your perspective on the future of design tooling and how companies can transition from current tools to more advanced, AI-integrated solutions.

📝 Enhancement Note: The emphasis on AI-native workflows and a "founding" role means candidates should prepare to articulate a strong strategic vision and demonstrate not just execution skills but also leadership and the ability to shape new processes and technologies.

🛠 Tools & Technology Stack

Primary Tools:

• Design System Components: React codebase for component implementation.

• Design & Prototyping: While moving away from traditional Figma-first, expect to work with advanced design tools and potentially AI-assisted design platforms. Familiarity with Figma is likely a baseline, but a strong point of view on next-generation tooling is critical.

• Documentation Platform: Tools for comprehensive design system documentation (e.g., Storybook, Zeroheight, or custom solutions).

• Collaboration Tools: Slack, video conferencing platforms (Zoom, Google Meet), project management tools (likely Ashby, Jira, Asana, or Trello).

Analytics & Reporting:

• Tools for tracking design system adoption and impact across products.

• Performance monitoring tools for front-end components. CRM & Automation:

• Not directly applicable to this role's core function, but understanding how the design system integrates with broader product development workflows is key. AI-Specific Tools:

• Claude: Hands-on experience with Claude and Claude Code is a significant plus, with the expectation to leverage these tools for generating on-system output.

📝 Enhancement Note: The core technology stack revolves around React for component implementation and advanced, potentially AI-driven, design tools. The ability to integrate and influence the adoption of these tools is paramount.

👥 Team Culture & Values

Operations Values:

• Scalability & Efficiency: A deep belief that design systems are the core infrastructure for building products rapidly and efficiently at scale.

• AI-First Mindset: Embracing AI as a fundamental collaborator in design and engineering, not an add-on.

• Technical Excellence: Commitment to high-quality code, robust architecture, and well-documented systems.

• Collaboration & Communication: Fostering strong partnerships between design, engineering, and product leadership.

• Innovation & Future-Forward: A drive to explore and define the next generation of design and development tooling and processes.

Collaboration Style:

• Proactive & Autonomous: Given the remote, founding-hire nature, expect a high degree of autonomy and the need for proactive communication and initiative.

• Partnership-Oriented: Close collaboration with engineering partners is essential, involving shared ownership of component implementation and quality.

• Influence-Driven: The ability to influence stakeholders across design, engineering, and product to align on design system strategy and adoption.

• Feedback-Rich: An environment that values constructive feedback for continuous improvement of both the design system and collaborative processes.

📝 Enhancement Note: The culture appears to be fast-paced, innovative, and focused on building robust infrastructure. The emphasis on AI and forward-thinking tooling suggests a team that values experimentation and is comfortable with change.

⚡ Challenges & Growth Opportunities

Challenges:

• Defining a New Paradigm: Establishing what an AI-native design system looks like from the ground up, moving beyond established practices.

• Cross-Team Alignment: Gaining buy-in and ensuring consistent adoption of the design system across five distinct products and multiple teams.

• Technical Implementation: Bridging the gap between design intent and robust, scalable code implementation, especially with evolving AI capabilities.

• Tooling Transition: Leading the shift from traditional design tools to new AI-integrated workflows, which may involve resistance or a learning curve.

• Building a Team: As the founding member, the challenge of defining the team's structure, hiring strategy, and culture as it grows.

Learning & Development Opportunities:

• AI Design Specialization: Becoming a leader in the emerging field of AI-native design systems.

• Leadership & Team Building: Developing skills in hiring, mentoring, and leading a design systems function.

• Advanced Front-End Architecture: Deepening expertise in building scalable, maintainable component libraries.

• Strategic Influence: Gaining experience in influencing product and engineering strategy at a senior level.

• Industry Conferences & Research: Staying at the forefront of AI and design system advancements through continuous learning and participation in relevant communities.

📝 Enhancement Note: This role presents a unique opportunity to tackle novel challenges in the AI and design systems space, offering significant growth potential for those who thrive in pioneering environments.

💡 Interview Preparation

Strategy Questions:

• "How would you approach building an AI-native design system from scratch for a company with five distinct products?" (Focus on your phased approach, key priorities, and AI integration strategy.)

• "Describe a time you had to influence multiple teams to adopt a new design system or pattern. What was your strategy and the outcome?" (Highlight your communication, persuasion, and stakeholder management skills.)

• "Imagine we're seeing inconsistent UI across our consumer web and mobile apps. How would you diagnose the root cause and what steps would you take to resolve it using a design system approach?" (Demonstrate your problem-solving methodology and understanding of system-level fixes.) Company & Culture Questions:

• "What are your thoughts on the future of design tooling in the age of AI? How do you see tools like Claude impacting design workflows?" (Showcase your forward-thinking perspective and understanding of AI's role.)

• "How do you see the relationship between design systems and engineering evolving with AI? What are the key collaboration points?" (Address your collaborative approach and how AI changes the dynamic.)

• "Given this is a founding hire for the design systems team, how would you define success for this role in the first 6-12 months?" (Articulate your strategic goals and measurable outcomes.) Portfolio Presentation Strategy:

• Narrative of Evolution: Frame your portfolio pieces not just as finished products, but as a journey of problem-solving, iteration, and impact, particularly showcasing how you've scaled systems.

• Technical Deep Dives: Be prepared to walk through the code or architecture of key components or system elements you've built. Explain your technical decisions and trade-offs.

• AI Integration Showcase: If you have relevant AI experience, dedicate a section or specific examples to this. Explain the "why" and "how" of your AI-driven design processes and their results.

• Quantifiable Results: Wherever possible, use data to illustrate the impact of your work – e.g., "Reduced design handoff time by X%," "Increased component reuse by Y%," "Improved UI consistency score by Z points."

• Leadership Vision: Conclude by articulating your vision for the design systems team at Cherry, including potential growth areas, hiring plans, and how you'd foster a collaborative culture.

📝 Enhancement Note: Candidates should prepare to demonstrate not only strong design and technical skills but also a strategic vision for the future of design systems in an AI-driven world, backed by concrete examples of leadership and impact.

📌 Application Steps

To apply for this operations position:

• Submit your application through the provided link on Ashby HQ.

• Tailor your resume: Highlight experience in design systems, product design, front-end development, AI integration, and any leadership roles. Use keywords from the job description such as "AI-native workflows," "design systems," "component architecture," and "React."

• Curate your portfolio: Select projects that best showcase your end-to-end design system experience, technical contributions, ability to scale systems, and any relevant AI work. Ensure it clearly articulates your strategic thinking and leadership capabilities.

• Prepare your case studies: Be ready to discuss specific examples of how you've improved design systems, collaborated with engineering, and influenced design direction, ideally with quantifiable results.

• Research Cherry: Understand their patient financing platform, target audience, and their commitment to AI-native workflows. Prepare to discuss how your vision aligns with their mission.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.