Staff Design Engineer - Design Systems

📍 Job Overview

Job Title: Staff Design Engineer - Design Systems

Company: Cherry Technologies, Inc.

Location: United States

Job Type: FULL_TIME

Category: Design Systems / Front-end Engineering

Date Posted: 2026-06-24

Experience Level: 5-10 Years

🚀 Role Summary

• Lead the strategic evolution and ownership of Cherry's comprehensive design system, encompassing component libraries, React codebase, interaction patterns, and design tokens across web and mobile platforms.

• Drive innovation in design infrastructure by integrating AI tooling (e.g., Claude, Cursor, Codex) to embed design rules and quality standards directly into development workflows, aiming to make the right design choices the default.

• Serve as a critical bridge between product design and front-end engineering, ensuring seamless adoption, consistent implementation, and scalable quality across multiple product surfaces.

• Define and champion the future vision for design systems in an AI-augmented era, moving beyond traditional maintenance to invent and build the next generation of design tooling and infrastructure.

📝 Enhancement Note: This role is positioned as a strategic, individual contributor with significant ownership and forward-thinking responsibilities. It requires a blend of deep technical expertise in React and front-end engineering, coupled with a strong product design sensibility and a visionary approach to design systems, particularly in the context of emerging AI technologies. The emphasis is on "reimagining" and "inventing" rather than "maintaining," indicating a high-impact, foundational role.

📈 Primary Responsibilities

• Design System Ownership & Development:

  • Take full ownership of the design system, including the React component library, interaction patterns, design tokens, and comprehensive documentation.
  • Write, ship, and maintain production-ready React code, adhering to high standards of code hygiene, robust testing practices, and clear architectural principles.
  • Define and enforce the visual and interaction design language for Cherry's component library, establishing the benchmark for all product surfaces.

• AI-Driven Quality at Scale:

  • Encode quality standards directly into the design system through components, tokens, and rules that simplify adherence to best practices.
  • Leverage AI tooling (Claude, Cursor, Codex) to embed design rules within development workflows, providing real-time quality guidance to teams.
  • Collaborate with the AI Enablement team to develop internal tools that expand the design system's capabilities and reach.

• Cross-Functional Collaboration & Partnership:

  • Partner closely with the front-end engineering team in Turkey on component architecture, implementation, and code review processes.
  • Act as the primary design system partner for the product design team, guiding system usage and fostering confident design contributions.
  • Work with the broader engineering organization to ensure components are easily adoptable, well-documented, and production-ready.

• Strategic Vision & Roadmap:

  • Own the strategic roadmap for the design system's evolution, particularly as AI transforms design and engineering workflows.

  • Define the long-term vision for components, pattern evolution, and process, anticipating future needs and industry shifts.

  • Advocate for the system's architectural integrity and long-term health, balancing immediate team needs with strategic objectives.

📝 Enhancement Note: The responsibilities highlight a dual focus on technical execution (React code, component architecture) and strategic leadership (AI integration, future vision). The emphasis on "encoding quality" and "making the right choice the easy choice" points to a systems-thinking approach to ensure scalability and consistency across a complex product ecosystem.

🎓 Skills & Qualifications

Education:

• While no specific degree is mandated, a strong portfolio and demonstrated expertise in front-end engineering and product design are paramount. Emphasis will be placed on practical application and problem-solving capabilities. Experience:

• 5-8+ years of combined experience in product design and front-end engineering, showcasing a balanced and deep understanding of both disciplines.

• Proven track record of building and maintaining design systems that are actively used by multiple teams in a production environment. Required Skills:

• React Expertise: Deep proficiency in React, with well-developed opinions on component architecture, state management, testing methodologies (e.g., Jest, React Testing Library), and overall code quality.

• Design System Proficiency: Expert-level skills in designing, building, and managing design systems, including component design, variant creation, token management, and documentation best practices.

• Visual & Interaction Design: A keen eye for detail in visual design (typography, color, spacing, hierarchy) and interaction design (animation, state transitions, user flows).

• AI Tooling Fluency: Demonstrated experience and comfort with AI-assisted development tools such as Claude Code, Cursor, or GitHub Copilot/Codex.

• Cross-Disciplinary Communication: Ability to articulate complex technical and design concepts effectively to diverse audiences, including designers, engineers, and product leadership.

• Production Code Quality: Strong understanding of code hygiene, architectural patterns, and robust testing practices for scalable software development.

Preferred Skills:

• Experience with TypeScript for enhanced code quality and maintainability.

• Familiarity with design tools beyond Figma, especially those focused on AI-driven workflows or custom tooling development.

• Experience in healthcare technology or patient financing sectors.

• Understanding of accessibility standards (WCAG) and their implementation within design systems.

• Experience with performance optimization for web and mobile applications.

📝 Enhancement Note: The requirements emphasize a "10x engineer" profile, blending deep technical skills with design acumen and a forward-thinking mindset. The explicit mention of AI tooling indicates a strong preference for candidates who are not only proficient in current technologies but are also eager to explore and shape the future of design infrastructure with AI.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Design System Case Studies: Showcase projects where you were instrumental in building, evolving, or scaling a design system. Detail the challenges, your approach, the system's architecture, and its impact on product velocity and consistency.

• React Component Development: Provide examples of complex React components you've built, highlighting code quality, testing strategies, and documentation. Include links to live examples or well-structured code repositories if possible.

• Design Token Implementation: Demonstrate experience with design tokens, including their structure, implementation across different platforms, and how they facilitate theming and consistency.

• AI Tooling Integration: If possible, include examples or descriptions of how you've used AI tools to enhance design or development workflows, particularly in the context of design systems or component development.

• Process Improvement Examples: Document instances where you've improved design or development processes through systemization, automation, or better tooling, with measurable outcomes.

Process Documentation:

• Evidence of creating clear, comprehensive, and maintainable documentation for design systems, components, and development guidelines.

• Examples of workflow designs that embed quality standards and streamline collaboration between design and engineering teams.

• Demonstrations of how you measure and communicate the effectiveness and impact of design system initiatives.

📝 Enhancement Note: The portfolio is critical for this role, serving as tangible proof of technical skill, design sensibility, and strategic thinking. Candidates should focus on demonstrating their ability to build robust, scalable systems and their proactive approach to incorporating new technologies like AI. The emphasis is on impact and measurable outcomes.

💵 Compensation & Benefits

Salary Range:

• Estimated Range: $170,000 - $220,000 USD annually.

• Methodology: This estimate is based on industry benchmarks for Staff Design Engineer roles in the US, considering the high demand for specialized skills in design systems, React expertise, and AI tooling integration. Factors include the experience level (5-8+ years), the importance of the role to the company's infrastructure, and the remote nature of the position. Salary will be commensurate with experience and qualifications.

Benefits:

• Comprehensive health, dental, and vision insurance.

• Generous paid time off (PTO) and holidays.

• Stock options or equity grants, reflecting the company's growth potential.

• Professional development budget for conferences, courses, and certifications relevant to design systems, front-end engineering, and AI.

• Remote work stipends for home office setup and internet.

• Access to cutting-edge AI tooling and internal AI Enablement resources.

• Opportunities to shape the future of design infrastructure in an innovative tech environment. Working Hours:

• Standard full-time position, approximately 40 hours per week.

• Flexible working hours are available, with an expectation of collaboration during core business hours and responsiveness to urgent needs. The team operates across different time zones, so asynchronous communication and clear documentation are key.

📝 Enhancement Note: The salary range is an estimate based on general market data for senior engineering roles in the US. Specific compensation will depend on the candidate's precise experience, skill set, and negotiation. The benefits package is typical for a growth-stage tech company, with a strong emphasis on professional development and remote work support.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology / Patient Financing. Cherry is disrupting the patient financing landscape by making healthcare more accessible through innovative financial solutions.

Company Size: As a growth-stage company, Cherry likely has between 50-200 employees, offering a dynamic environment where individual contributions have a significant impact.

Founded: While the founding date isn't specified, the company's focus on AI and reimagining design infrastructure suggests a relatively modern and forward-thinking organization.

Team Structure:

• The Design Systems team is likely small and highly specialized, reporting into a Head of Engineering or a VP of Product/Engineering.

• This role will be a key individual contributor, working closely with product designers, front-end engineers (especially those in Turkey), and the dedicated AI Enablement team.

• Collaboration is expected to be cross-functional, involving product managers, other engineering teams, and potentially leadership. Methodology:

• Data-Driven Evolution: Design system decisions are informed by usage data, team feedback, and strategic business goals.

• AI Integration: A core part of the company's methodology is the proactive adoption and development of AI tooling to enhance efficiency and quality.

• Infrastructure Mindset: Design systems are viewed as foundational infrastructure, critical for enabling rapid and consistent product development.

Company Website: https://withcherry.com/

📝 Enhancement Note: Cherry's focus on AI and reimagining design systems suggests a culture that values innovation, technical excellence, and a proactive approach to problem-solving. The company's mission in healthcare financing implies a desire to make a tangible positive impact.

📈 Career & Growth Analysis

Operations Career Level:

• This is a "Staff" level position, signifying a senior individual contributor role. It implies a deep level of technical expertise, strategic thinking, and the ability to influence technical direction across multiple teams. Staff engineers are expected to tackle ambiguous problems, mentor others, and drive significant technical initiatives. Reporting Structure:

• The Staff Design Engineer will likely report to a Director or VP of Engineering, or a Head of Product. They will work closely with product design leads and engineering managers. Operations Impact:

• The design system is the bedrock of product quality and development speed at Cherry. This role directly impacts the efficiency of design and engineering teams, the consistency and quality of user experiences across all products, and the company's ability to innovate rapidly, especially with AI integration. A well-functioning design system is a key enabler of GTM strategy by reducing time-to-market and ensuring a cohesive brand experience. Growth Opportunities:

• Technical Leadership: Transition into a Principal Engineer role, or lead a dedicated Design Systems team as it grows.

• Specialization: Deepen expertise in AI for design/engineering tooling, or focus on specific areas like accessibility or performance within design systems.

• Cross-Functional Expansion: Move into broader front-end architecture roles or product engineering leadership positions.

• Mentorship: Guide and mentor junior engineers and designers on best practices for design systems and front-end development.

📝 Enhancement Note: The "Staff" title indicates a role with significant autonomy and influence. Growth opportunities are geared towards deepening technical expertise, developing leadership skills, or expanding into broader architectural responsibilities. The emphasis on AI integration presents a unique avenue for specialized growth.

🌐 Work Environment

Office Type:

• The role is designated as "TELECOMMUTE," indicating a fully remote position within the United States. This suggests a company culture that trusts its employees and is set up to support distributed teams effectively. Office Location(s):

• While the role is remote, the company headquarters are in the United States. The mention of a front-end engineering team in Turkey suggests a global, distributed team structure. Workspace Context:

• Collaborative Tooling: Expect extensive use of collaboration tools like Slack, Zoom, and shared documentation platforms (e.g., Notion, Confluence) for seamless remote interaction.

• AI-Powered Workflows: The environment will be deeply integrated with AI tools, both for development (Cursor, Claude) and potentially for communication and task management.

• Cross-Team Interaction: Opportunities to engage with diverse teams, including product design, front-end engineering (globally), AI Enablement, and product management, fostering a rich learning and collaboration experience.

Work Schedule:

• Flexible working hours are standard for remote roles, allowing individuals to manage their schedules effectively. However, core collaboration hours will be necessary for team meetings, code reviews, and cross-functional syncs, likely aligning with US business hours.

📝 Enhancement Note: The remote-first nature of this role requires strong self-discipline, excellent asynchronous communication skills, and a proactive approach to collaboration. The company's commitment to AI suggests a modern, tech-forward work environment.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with a recruiter to assess basic qualifications, cultural fit, and interest in the role and company mission.

• Technical/Design Screen: A conversation with a member of the design systems or engineering team to dive deeper into your experience with React, design systems, and AI tooling. This may involve discussing specific projects from your portfolio.

• Design System Deep Dive: A dedicated session to present your portfolio, focusing on one or two key design system projects. Expect to discuss your approach to architecture, collaboration, challenges, and impact. This is where your ability to articulate strategy and technical decisions will be evaluated.

• Cross-Functional/Engineering Interview: A session with engineering leaders and potentially product managers to assess your ability to collaborate, communicate across disciplines, and understand broader product development challenges.

• Final Interview/Executive Conversation: A meeting with a senior leader (e.g., VP of Engineering) to discuss strategic vision, cultural alignment, and long-term career aspirations.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the business and technical impact of your design system work. Quantify results where possible (e.g., reduced development time, improved consistency scores, increased adoption rates).

• Showcase AI Integration: Highlight any projects or initiatives where you've leveraged AI tools to improve design system development, documentation, or implementation.

• Demonstrate "Staff" Level Thinking: Go beyond describing features; explain the "why" behind your decisions, the trade-offs you considered, and your strategic vision for the system's future.

• Prepare for Technical Depth: Be ready to discuss React architecture, component patterns, testing strategies, and code quality in detail.

• Tell a Story: Structure your portfolio presentation as a narrative, guiding the interviewers through the problem, your solution, and the outcomes.

Challenge Preparation:

• Be prepared for potential take-home assignments or live coding exercises that assess your React skills, problem-solving abilities, and approach to building components or system logic.

• Practice articulating your thought process clearly and concisely, especially when working through technical challenges or design problems.

📝 Enhancement Note: The interview process is designed to assess a unique blend of skills. Candidates should be prepared to demonstrate both deep technical proficiency and a strategic, forward-looking perspective, with a strong emphasis on how AI can transform design systems.

🛠 Tools & Technology Stack

Primary Tools:

• React: The core JavaScript library for building user interfaces. Deep proficiency is essential.

• AI-Assisted Development: Claude Code, Cursor, GitHub Copilot/Codex. Fluency and a willingness to explore new AI tools are critical.

• Design Tools: Currently Figma, with an active transition toward AI-native tooling. Experience with Figma's component system, variants, and tokens is expected, alongside an openness to new paradigms.

• Version Control: Git (e.g., GitHub, GitLab, Bitbucket).

• Package Management: npm or Yarn.

Analytics & Reporting:

• Tools for tracking design system adoption and component usage (specific tools not detailed, but likely integrated into development workflows or via analytics platforms).

• Performance monitoring tools to ensure component efficiency. CRM & Automation:

• Not directly applicable to this role, but understanding how the design system supports broader product development and GTM initiatives is valuable.

📝 Enhancement Note: The technology stack emphasizes modern front-end development practices and a strong commitment to AI integration. Candidates should be comfortable with the given tools and eager to adapt to new technologies as the company transitions its design tooling.

👥 Team Culture & Values

Operations Values:

• Innovation & Future-Forward: A drive to explore and implement cutting-edge technologies, particularly AI, to redefine best practices.

• Quality & Craftsmanship: A commitment to building robust, well-engineered, and polished systems that set a high standard.

• Collaboration & Partnership: A belief in working closely with cross-functional teams to achieve shared goals and ensure system adoption.

• Ownership & Accountability: Taking full responsibility for the design system's success, from strategy to execution.

• Efficiency & Scalability: Designing systems that enable faster, more consistent product development across the organization.

Collaboration Style:

• Asynchronous First: Given the remote and distributed nature of the team, clear written communication and well-maintained documentation are paramount.

• Proactive Communication: Encouraging team members to share updates, ask questions, and provide feedback openly.

• Design & Engineering Synergy: Fostering a close working relationship where designers and engineers understand each other's perspectives and constraints.

• Mentorship & Knowledge Sharing: A culture where senior members actively mentor and share their expertise with others.

📝 Enhancement Note: The company values suggest a culture that is both technically ambitious and highly collaborative, with a strong emphasis on building scalable, high-quality products through innovation, particularly with AI.

⚡ Challenges & Growth Opportunities

Challenges:

• Transitioning Design Tooling: Leading the shift away from Figma towards new, AI-native design tools requires strategic planning, buy-in, and technical execution.

• Balancing Diverse Needs: The design system must serve multiple products (web, mobile, POS) and diverse teams, requiring careful prioritization and flexible architecture.

• Encoding AI into Systems: Defining how AI tools can effectively and reliably integrate into design system workflows is a novel challenge with significant potential.

• Maintaining Momentum: Ensuring the long-term health and evolution of the design system while balancing feature requests and architectural improvements.

Learning & Development Opportunities:

• AI in Design/Engineering: Become a leader in applying AI to design systems and front-end development workflows.

• Advanced React Architecture: Deepen expertise in complex React patterns, performance optimization, and scalable component libraries.

• Cross-Functional Leadership: Develop skills in influencing and guiding product strategy through technical and design leadership.

• Industry Best Practices: Stay at the forefront of design system methodologies and AI advancements through conferences, research, and experimentation.

📝 Enhancement Note: The challenges are directly tied to the innovative nature of the role, particularly around AI integration and the evolution of design tooling. Growth opportunities are significant for someone looking to make a mark in a rapidly evolving field.

💡 Interview Preparation

Strategy Questions:

• "How would you approach migrating a design system from Figma to a new, AI-native tooling paradigm, and what are the key considerations for ensuring continuity and adoption?"

• "Describe a time you had to advocate for a significant architectural change in a design system. What was the challenge, how did you approach it, and what was the outcome?"

• "Given the increasing role of AI in development, how do you envision design systems evolving, and what specific steps would you take at Cherry to lead this evolution?"

• "How do you balance the needs of multiple product teams with the need for architectural consistency and long-term maintainability in a design system?" Company & Culture Questions:

• "What excites you about Cherry's mission in patient financing and healthcare technology, and how does that align with your career goals?"

• "How do you see your role as a Staff Design Engineer contributing to Cherry's overall product strategy and GTM success?"

• "Describe your ideal collaboration with product designers and front-end engineers. What makes for a successful partnership?" Portfolio Presentation Strategy:

• Structure: Start with an overview of the company/project, define the problem/challenge, detail your specific contributions and technical approach (especially React and design system architecture), highlight the impact and outcomes, and conclude with lessons learned and future plans.

• Quantify Impact: Use metrics to demonstrate the value of your work (e.g., "Reduced component development time by X%", "Increased design consistency scores by Y%").

• Focus on AI: Explicitly discuss any AI tools used, the benefits realized, and your vision for further AI integration within the design system.

• Be Ready for Deep Dives: Anticipate detailed questions about your code, design decisions, and problem-solving methodologies.

📝 Enhancement Note: Interview preparation should focus on demonstrating strategic thinking, technical depth, and a clear vision for the future of design systems, especially in the context of AI. Candidates need to articulate not just what they did, but why and how it had a significant impact.

📌 Application Steps

To apply for this Staff Design Engineer position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Tailor your portfolio to highlight projects demonstrating deep React expertise, comprehensive design system experience, and any work involving AI-assisted development tools or innovative tooling solutions.

• Resume Optimization: Ensure your resume clearly articulates your 5-8+ years of experience, specifically mentioning proficiency in React, design systems, and AI tooling. Use keywords from the job description and quantify your achievements.

• Interview Preparation: Practice presenting your portfolio, focusing on articulating the "why" behind your technical and design decisions, and be ready to discuss your vision for AI's role in design systems. Prepare specific examples of how you've driven quality and efficiency at scale.

• Company Research: Understand Cherry's mission in patient financing and their commitment to AI. Prepare thoughtful questions about their long-term vision for design infrastructure and the company's culture.

⚠️ 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.