Senior Product Designer, Design Systems

📍 Job Overview

Job Title: Senior Product Designer, Design Systems

Company: Headway

Location: New York, NY; San Francisco, CA; Seattle, WA

Job Type: FULL_TIME

Category: Product Design / Design Systems

Date Posted: 2026-09-14

Experience Level: 5-10 Years

Remote Status: Hybrid

🚀 Role Summary

• Spearhead the evolution and implementation of Headway's Design System, "Helix," focusing on enhancing user experience across consumer and EHR platforms.

• Drive best-in-class visual craft and systems thinking to establish scalable and flexible design components and patterns.

• Collaborate closely with engineering and product teams to ensure seamless integration and adoption of design system standards.

• Champion accessibility and inclusive design principles throughout the design system lifecycle.

• Contribute to an AI-first design environment, integrating AI tooling within the design system for enhanced prototyping and workflow efficiency.

📝 Enhancement Note: This role is critical for scaling Headway's product offerings by ensuring consistency, efficiency, and quality across all digital touchpoints. The focus on an "AI-first" approach within design systems is a forward-thinking aspect that requires candidates to be adaptable and innovative in their design process.

📈 Primary Responsibilities

• Design and refine flexible, scalable UI components, meticulously holding high standards for typography, spacing, color, states, and density.

• Develop and maintain comprehensive Figma library components, ensuring variants and properties are accurately defined for engineer handoff.

• Shape the semantic token architecture and the theming specification to ensure cohesive design across diverse surfaces, from consumer marketplaces to internal operational tools.

• Create clear, actionable documentation for designers, engineers, and AI coding agents to facilitate understanding and adoption of the design system.

• Partner with product designers and engineers to address their design system needs, advocate for best practices, and develop migration plans for component updates.

• Champion and enforce accessibility standards (WCAG AA or higher) within the Helix design system to ensure inclusive product experiences.

• Contribute to the AI-first design culture by exploring and integrating AI tooling into the design system's workflow and documentation.

• Collaborate with the Design Systems Lead to define the strategic roadmap and future evolution of the Helix design system.

• Conduct design reviews to ensure adherence to the design system and provide constructive feedback to product teams.

• Proactively identify gaps in the design system and propose solutions that address both immediate needs and long-term scalability.

📝 Enhancement Note: The responsibilities highlight a blend of deep design craft, technical understanding of system architecture (tokens, APIs), and strong collaboration skills. The emphasis on documentation for multiple audiences (designers, engineers, AI agents) is a key differentiator for this role.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience.

Experience: 5+ years of experience designing digital products, with a minimum of two years specifically focused on building and maintaining design systems used by multiple product teams.

Required Skills:

• Proven expertise in visual craft, with a strong command of typography, spacing, color theory, states, and density for creating polished UIs.

• Deep understanding of systems thinking and the ability to design flexible, scalable, and maintainable design components and patterns.

• Proficiency in Figma for component creation, variant definition, property setup, and library management.

• Experience designing and implementing token architecture and theming strategies for diverse product surfaces.

• Demonstrated ability to write clear, concise, and actionable documentation for both design and engineering audiences.

• Strong understanding of accessibility standards (e.g., WCAG) and experience applying them to component design.

• Experience working within an Agile development environment and collaborating effectively with engineers.

• Ability to translate complex requirements into elegant and user-friendly design solutions.

• Excellent communication, presentation, and interpersonal skills, with the ability to advocate for design system principles. Preferred Skills:

• Hands-on experience with front-end development frameworks such as React and CSS frameworks like Tailwind CSS.

• Familiarity with AI-first design workflows and tools (e.g., Claude Code, Claude Design).

• Experience designing for both consumer-facing applications and internal/SaaS tools.

• Experience with API design best practices relevant to component interaction.

• Familiarity with design tokens and their implementation across different platforms.

• Experience mentoring or guiding junior designers on design system best practices.

📝 Enhancement Note: The requirement for 5+ years of experience with at least two years specifically in design systems indicates a need for a seasoned professional who can operate with a high degree of autonomy and strategic input. The preference for React and Tailwind suggests a closer collaboration with front-end development.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrates a clear understanding of design systems principles, including component structure, variants, and properties.

• Showcases case studies detailing the design and implementation of scalable UI components, emphasizing visual craft and attention to detail.

• Includes examples of token architecture and theming strategies, illustrating how the system adapts to different brand expressions or product needs.

• Features well-documented examples of design system usage by multiple teams, highlighting the impact on consistency and efficiency.

• Presents strong examples of accessibility considerations and solutions implemented within a design system context.

• May include examples of documentation created for designers and engineers, showcasing clarity and actionability. Process Documentation:

• Provide evidence of your process for designing and documenting components, including how you define variants, states, and interactions.

• Detail your approach to establishing and evolving semantic design tokens and theming rules.

• Illustrate your method for collaborating with engineers and product teams to ensure successful adoption and integration of the design system.

• Showcase your strategy for creating comprehensive documentation that supports designers, developers, and potentially AI agents.

📝 Enhancement Note: Candidates will need to present a portfolio that not only showcases visual design skills but also a deep understanding of system architecture, process, and the ability to create scalable and maintainable design solutions. The emphasis on documentation for AI agents is a unique requirement.

💵 Compensation & Benefits

Salary Range: $180,000 - $225,000 USD per year.

Benefits:

• Equity compensation

• Medical, Dental, and Vision coverage

• Health Savings Account (HSA) / Flexible Spending Account (FSA)

• 401K retirement plan

• Work-from-Home Stipend

• Therapy Reimbursement

• 16-week parental leave for eligible employees

• Carrot Fertility annual reimbursement and membership

• 13 paid holidays annually, plus a Holiday Break between December 25th and December 31st

• Flexible Paid Time Off (PTO)

• Employee Assistance Program (EAP)

• Training and professional development opportunities

Working Hours: Full-time position, likely aligning with standard US business hours (e.g., 40 hours per week), with flexibility offered through the PTO policy.

📝 Enhancement Note: The salary range provided is competitive for a Senior Product Designer role in major tech hubs like New York, San Francisco, and Seattle, especially for a specialized Design Systems position. The benefits package is comprehensive, reflecting a company investing in employee well-being and professional growth.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology (Mental Healthcare focus)

Company Size: Series D funded, indicating significant growth and established operations (likely 200-500+ employees).

Founded: Headway was founded to address the accessibility gap in mental healthcare by simplifying insurance processes for providers and patients. This mission drives a culture focused on impact and innovation.

Team Structure:

• The Design team is structured to support a large product organization, with a dedicated focus on Design Systems.

• The Design Systems team operates as a central function, providing foundational elements and guidance to multiple product teams.

• Collaboration is expected to be cross-functional, involving Product Managers, Engineers, and other Designers.

• The role reports to the Design Systems Lead, indicating a clear hierarchy within the design systems function. Methodology:

• Headway adopts an "AI-first" approach to product development, integrating AI tools like Claude Code and Claude Design into the design and prototyping process.

• Design systems are viewed as critical enablers for this AI-first strategy, requiring systems that can be leveraged effectively by AI.

• Emphasis is placed on shipping high-quality, well-documented components and patterns that empower product teams.

• Continuous iteration and improvement are key, as evidenced by the current rebuilding of the Helix design system.

Company Website: https://headway.co/

📝 Enhancement Note: Headway's mission to improve mental healthcare access is a strong cultural anchor. The "AI-first" methodology suggests a forward-thinking and technologically advanced environment, which will appeal to designers interested in cutting-edge practices.

📈 Career & Growth Analysis

Operations Career Level: Senior Product Designer. This level signifies a high degree of autonomy, expertise, and the ability to influence product direction and team best practices. The role is responsible for leading significant design system initiatives.

Reporting Structure: The Senior Product Designer will report to the Design Systems Lead, working closely with them to execute the design system strategy. This structure allows for mentorship and direct contribution to the system's evolution.

Operations Impact: The work directly impacts product consistency, developer efficiency, and the overall user experience for both patients and therapists. By maintaining and evolving the Helix design system, this role contributes to Headway's mission of making mental healthcare accessible.

Growth Opportunities:

• Deepen expertise in design systems, potentially growing into a Design Systems Lead or Manager role.

• Develop specialized skills in AI-assisted design workflows and the integration of AI into design systems.

• Gain experience working within a rapidly scaling Series D startup in the high-impact healthcare technology sector.

• Opportunities for cross-functional leadership and mentorship of other designers.

• Contribute to the foundational architecture of a critical product system, influencing the long-term trajectory of Headway's products.

📝 Enhancement Note: This role offers significant growth potential for individuals passionate about design systems and the intersection of AI and design. The opportunity to rebuild a core system from the ground up is a substantial career development experience.

🌐 Work Environment

Office Type: The job is listed as Hybrid, indicating a blend of remote work and in-office presence. Specific office locations are in New York, San Francisco, and Seattle.

Office Location(s):

• New York, NY

• San Francisco, CA

• Seattle, WA Workspace Context:

• The hybrid model allows for flexibility, combining focused remote work with collaborative in-office sessions.

• The company emphasizes an "AI-first" approach, suggesting access to modern design and development tools.

• Collaboration is key, with opportunities to work closely with a Design Systems Lead, product designers, and engineers.

• The work environment likely supports continuous learning and professional development, as noted in the benefits.

Work Schedule: Standard full-time work week, likely 40 hours. The hybrid nature and flexible PTO policy suggest a focus on output and work-life balance rather than strict adherence to hours.

📝 Enhancement Note: The hybrid nature in major tech hubs provides flexibility while maintaining opportunities for in-person collaboration, which is often crucial for design system work.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter will likely review your application and portfolio to assess basic qualifications and fit.

• Portfolio Review & Design Challenge: Expect to present your portfolio, focusing on design system examples. A practical design challenge may be given, potentially involving component design, documentation, or token application, possibly with an AI integration aspect.

• Hiring Manager/Team Interviews: Discussions with the Design Systems Lead and potentially other senior designers or engineering leads to delve deeper into your experience, systems thinking, technical skills, and collaboration style.

• Cross-functional Interviews: Meetings with product managers or engineers to evaluate your ability to partner effectively and understand their needs.

• Final Round: Potentially a discussion with a design leader or executive to assess cultural fit and strategic alignment.

Portfolio Review Tips:

• Highlight Design System Expertise: Showcase 2-3 detailed case studies specifically on design systems you've worked on. Emphasize your role, the challenges, your solutions, and the impact.

• Demonstrate Visual Craft: Ensure your examples exhibit high standards in typography, spacing, color, and states.

• Showcase Systemic Thinking: Clearly articulate how your designs are scalable, flexible, and maintainable. Explain your approach to token architecture and theming.

• Document Your Process: Include examples of documentation you've created for designers and engineers. Explain your process for creating and maintaining these assets.

• Address Accessibility: Explicitly mention how you incorporate accessibility into your design system work.

• Quantify Impact: If possible, use metrics to demonstrate the value your design system work brought (e.g., reduced design/dev time, increased consistency).

• AI Integration: If you have relevant experience, highlight how you've used or considered AI in your design system workflows.

Challenge Preparation:

• Component Design: Be prepared to design a new component or refine an existing one based on given requirements, considering variants, states, and accessibility.

• Token Application: Practice applying design tokens to different UI elements and scenarios.

• Documentation Writing: Be ready to write documentation for a component or pattern, considering different audiences.

• System Thinking Scenarios: Think through how you would address a request that could be a one-off vs. a system-wide pattern.

• Technical Familiarity: Be ready to discuss how your designs would be implemented in React and Tailwind CSS.

📝 Enhancement Note: The emphasis on AI-first design and documentation for AI agents means candidates should be prepared to discuss their understanding of these emerging areas and how they might apply them within a design system context.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The primary tool for UI design, component creation, and library management. Expertise in advanced features like variants, properties, and auto layout is essential.

• Design System Platforms/Tools: While not explicitly named, expect familiarity with tools for managing design tokens, versioning, and distribution.

• Prototyping Tools: Beyond Figma's capabilities, potentially tools like Principle, ProtoPie, or even custom code for advanced prototypes.

Analytics & Reporting:

• While not a direct analytics role, understanding how design system usage is tracked and how to interpret user feedback and performance data is beneficial. Tools like Amplitude, Mixpanel, or internal dashboards might be used to gauge adoption and impact. CRM & Automation:

• Not directly applicable to this role, but understanding how design systems support broader product automation and user flows within CRM contexts could be a plus. Development & Implementation Focus:

• React: Strong familiarity with React is preferred for understanding how components are built and for potentially contributing to simpler component development.

• Tailwind CSS: A preferred skill, indicating the company's front-end stack and the need for designers to understand utility-first CSS for effective design system implementation.

• Version Control (e.g., Git): Understanding of how design system assets are versioned and managed in a development workflow.

• AI Tooling: Exposure to AI design tools like Claude Code and Claude Design for prototyping and workflow enhancement.

📝 Enhancement Note: The explicit mention of React and Tailwind CSS is a strong indicator of the technical stack and the level of engineering collaboration expected from this design role. Familiarity with AI design tools is a unique and important requirement.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to Headway's mission of making mental healthcare accessible. This translates to a desire to build products that have a tangible positive impact.

• Craftsmanship & Quality: Holding a high bar for design craft, visual detail, and technical execution. This means prioritizing quality in every component and pattern.

• Collaboration & Partnership: Working effectively with cross-functional teams (product, engineering) to achieve shared goals. The design system is a collaborative effort.

• Innovation & Forward-Thinking: Embracing new technologies and methodologies, particularly the "AI-first" approach to design and development.

• Empowerment & Enablement: Building systems that empower other designers and engineers to build faster and more consistently.

Collaboration Style:

• Partnership with Engineering: Close collaboration with front-end engineers on implementation, API design, and ensuring technical feasibility.

• Support for Product Teams: Acting as a resource and advocate for product designers, helping them leverage the design system effectively.

• AI Integration: Exploring and integrating AI tools into workflows, fostering a culture of experimentation and learning.

• Feedback-Oriented: Openness to feedback from all stakeholders to continuously improve the design system and related processes.

• Documentation-Centric: Valuing clear and accessible documentation as a primary means of communication and knowledge sharing.

📝 Enhancement Note: The culture emphasizes impact, quality, and innovation, with a strong collaborative spirit, especially between design and engineering. The AI-first aspect suggests a dynamic and evolving team environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Needs: Designing a system that serves diverse needs across consumer-facing apps and dense internal tools requires careful consideration of flexibility and constraints.

• AI Integration: Effectively integrating AI into design system workflows and documentation presents a novel challenge that requires creative problem-solving and experimentation.

• Adoption and Migration: Ensuring widespread adoption of the design system and managing migration plans for existing products can be complex and require strong advocacy.

• Maintaining High Craft: Upholding a high standard of visual craft and accessibility across a rapidly growing product suite requires constant vigilance and clear guidelines.

• Rebuilding from Scratch: Contributing to the foundational rebuild of Helix means shaping its future direction, which is both an opportunity and a challenge requiring strategic foresight.

Learning & Development Opportunities:

• Advanced Design Systems: Deepen expertise in areas like token architecture, theming, accessibility, and design system governance.

• AI in Design: Gain hands-on experience with AI-powered design tools and explore their application in creating more efficient and innovative design processes.

• Front-end Development Collaboration: Enhance understanding of React and Tailwind CSS through close partnership with engineers.

• Product Strategy: Contribute to the strategic direction of Headway's product ecosystem by building foundational design elements.

• Mentorship: Opportunity to mentor junior designers and contribute to the growth of the design team.

📝 Enhancement Note: The opportunity to rebuild a core design system is a significant challenge and growth area. The AI focus offers unique learning potential in a rapidly evolving field.

💡 Interview Preparation

Strategy Questions:

• "Describe your approach to designing a new component for a design system. What factors do you consider beyond just the visual appearance?" (Focus on scalability, variants, states, accessibility, documentation, and engineering feasibility).

• "How do you balance the needs of different product teams when designing a design system? Can you give an example of a time you had to negotiate competing requirements?" (Highlight collaboration, communication, and systems thinking).

• "Explain your philosophy on design tokens and theming. How would you approach creating a token system that supports both a consumer marketplace and an internal ops tool?" (Discuss semantic tokens, hierarchy, and adaptability).

• "How do you ensure accessibility is integrated into a design system from the ground up?" (Detail specific practices, testing, and documentation).

• "Given our AI-first approach, how might you approach designing documentation for a component that would be usable by both designers and AI coding agents?" (Focus on structured data, clear language, and potential for machine readability). Company & Culture Questions:

• "What interests you about Headway's mission to improve mental healthcare access?" (Connect your personal values or past experiences to the mission).

• "How do you see a design system supporting an 'AI-first' product development strategy?" (Discuss efficiency, consistency, and enablement).

• "Describe your experience working in a hybrid environment. How do you maintain strong collaboration with remote and in-office team members?" (Highlight communication tools and strategies).

• "How do you advocate for design system best practices within a product organization?" (Discuss education, support, and partnership). Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly outline the problem, your role, the process, the solution, and the impact.

• Show, Don't Just Tell: Use visuals extensively. Show your Figma files, component examples, token structures, and documentation snippets.

• Focus on Design Systems: Prioritize projects that demonstrate your experience with design systems, component design, and system architecture.

• Highlight Technical Collaboration: Explain how you worked with engineers and how your designs translated into code.

• Address AI Integration: If applicable, showcase any work or thoughts on integrating AI into your design system process.

• Be Ready for Deep Dives: Prepare to answer detailed questions about your design decisions, technical considerations, and process.

• Practice Your Pitch: Rehearse your presentation to ensure it's concise, engaging, and within the allotted time.

📝 Enhancement Note: The interview process will heavily scrutinize your design systems expertise, technical understanding, and ability to integrate AI into your workflow. Be prepared to discuss specific examples and articulate your strategic thinking.

📌 Application Steps

To apply for this Senior Product Designer, Design Systems position:

• Submit your application through Headway's official careers page: https://headway.co/careers

• Tailor Your Resume: Highlight your experience with design systems, component design, visual craft, and any experience with React, Tailwind CSS, or AI design tools. Quantify achievements where possible.

• Curate Your Portfolio: Select 2-3 strong design system case studies that showcase your skills in component design, token architecture, accessibility, and documentation. Ensure it reflects the requirements outlined above.

• Prepare Your Narrative: Practice presenting your portfolio, focusing on your process, decisions, and the impact of your work, especially regarding design systems and potentially AI integration.

• Research Headway: Understand their mission, product, and the "AI-first" approach to better tailor your application and interview responses.

⚠️ 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.

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