Design Director, Provider Experience

📍 Job Overview

Job Title: Design Director, Provider Experience

Company: Headway

Location: San Francisco, CA, United States

Job Type: FULL_TIME

Category: Product Design / UX Leadership

Date Posted: 2026-06-04

Experience Level: 5+ years leading design teams (AI-generated based on description)

Remote Status: On-site (AI-generated based on location and description)

🚀 Role Summary

• Drive the overarching design strategy and vision for Headway's Provider EHR (Electronic Health Record) experience, focusing on an AI-native practice management ecosystem.

• Lead, mentor, and grow a talented team of designers, fostering a culture of high craft, innovation, and continuous improvement in user experience design.

• Act as a player-coach, taking ownership of key strategic design initiatives and hands-on execution, particularly in the development of AI-augmented features.

• Ensure seamless integration and coherence between the provider-facing EHR experience and patient-facing flows, as well as marketplace capabilities like search and onboarding.

📝 Enhancement Note: This role is positioned as a critical leadership opportunity within a rapidly growing, mission-driven health tech company. The emphasis on "AI-native" experiences and the requirement for designers to actively use AI tools (Claude, Cursor, MagicPatterns) for prototyping and development indicate a forward-thinking design approach. The "player-coach" aspect suggests a need for a leader who can not only strategize and manage but also contribute directly to design execution and innovation. The target audience for this role would be experienced design leaders with a strong background in complex B2B SaaS, a passion for healthcare technology, and a proactive stance on leveraging AI in product development.

📈 Primary Responsibilities

• Define and champion the strategic vision for the provider EHR experience, collaborating with Product, Engineering, and senior leadership to shape the future of AI-native practice management.

• Recruit, hire, and manage a high-performing design team, establishing rigorous design standards and fostering an environment of continuous learning and mentorship.

• Lead the end-to-end design process for critical AI-native features, from conceptualization and user research to prototyping, iteration, and implementation.

• Develop and maintain a cohesive design experience across all provider touchpoints, ensuring consistency and seamless user journeys from scheduling to documentation and client engagement.

• Actively utilize AI tools (Claude, Cursor, MagicPatterns) for rapid prototyping, exploring design patterns, and generating code, thereby accelerating the design-to-launch cycle.

• Collaborate closely with user research teams and directly engage with mental health providers to gather insights, validate design solutions, and ensure product-market fit.

• Contribute to the evolution of Headway's design system and foster a strong design culture by sharing AI best practices, prompts, and innovative patterns with the broader design organization.

📝 Enhancement Note: The responsibilities highlight a dual focus on strategic leadership and hands-on contribution. The expectation to use AI tools directly in the design process is a significant differentiator for this role, requiring a candidate who is not only a skilled designer but also an early adopter and innovator in AI-assisted design workflows. The emphasis on cross-functional collaboration and the "player-coach" model suggests a dynamic, fast-paced environment where leaders are expected to be both strategic thinkers and doers.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong understanding of design principles, UX methodologies, and product development is essential, often gained through formal education or equivalent practical experience.

Experience: 5+ years of experience leading design teams for complex B2B SaaS platforms with a focus on delivering consumer-grade user experiences. Experience within hyper-growth startups (Series C+) or companies with mature design practices is highly valued.

Required Skills:

• Proven experience in Design Leadership, including team management, hiring, and mentorship.

• Expertise in designing for complex B2B SaaS platforms, with a strong emphasis on User Experience (UX) and user-centered design principles.

• Demonstrated experience designing AI-native or AI-augmented product experiences, with a deep understanding of how AI can fundamentally transform workflows.

• Proficiency in using AI tools (e.g., Claude, Cursor, MagicPatterns) for rapid prototyping, iterating on design solutions, and generating code.

• Strong Product Strategy and Design Thinking capabilities, with the ability to translate business objectives into compelling user experiences.

• Hands-on experience with Prototyping tools and techniques, coupled with the ability to quickly iterate based on user feedback and AI-generated insights.

• Experience in developing and maintaining Design Systems to ensure scalability and consistency across products.

• Excellent cross-functional collaboration skills, with a proven ability to partner effectively with Product Management, Engineering, and senior leadership.

• Experience conducting User Research and translating findings into actionable design improvements.

• Strong understanding of Information Architecture and its impact on complex application usability. Preferred Skills:

• Experience in the healthcare technology sector, particularly with Electronic Health Records (EHR) or practice management software.

• Familiarity with AI-powered features such as transcript-powered notes, AI-enabled scheduling, or co-pilot functionalities.

• Experience working in a hyper-growth startup environment (Series C+).

• A portfolio that showcases both high-craft individual design work and systematic approaches to designing scalable solutions.

📝 Enhancement Note: The requirements strongly emphasize practical, hands-on experience with AI design tools and a strategic approach to AI-native product development. The "player-coach" aspect implies that candidates should be comfortable leading and executing simultaneously. The portfolio requirement is critical, needing to showcase both leadership in design strategy and individual contribution to complex B2B SaaS products, ideally with examples of AI integration.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate a strong understanding of the entire product development lifecycle, from initial concept to launch and iteration, with a focus on B2B SaaS applications.

• Showcase examples of leading design teams and influencing product strategy and organizational direction through design thinking.

• Present case studies that highlight the design of AI-native or AI-augmented product experiences, detailing the problem, your process, the AI tools used, and the resulting impact.

• Include examples of systematic approaches to design at scale, such as contributions to design systems or the development of scalable UI patterns.

• Provide evidence of hands-on work using AI tools like Claude, Cursor, or MagicPatterns for prototyping, and discuss how AI was leveraged to enhance efficiency and innovation in the design process. Process Documentation:

• Clearly articulate your process for user research, including methods for direct engagement with users (in this case, mental health providers) to validate solutions.

• Detail your approach to defining experience vision and strategy in partnership with Product and Engineering, particularly for complex, multi-faceted workflows like EHR systems.

• Explain your methodology for ensuring design coherence across different product pillars and user journeys (provider EHR, patient flows, marketplace).

• Showcase how you have contributed to or managed the development and evolution of design systems, ensuring consistency and scalability.

📝 Enhancement Note: The portfolio is a critical component for this role, needing to not only demonstrate design excellence but also leadership capabilities and a forward-thinking approach to AI integration. Candidates should be prepared to walk through their process, especially how they've leveraged AI tools and managed design at scale within a B2B SaaS context. The emphasis on "AI-native" means the portfolio should actively highlight projects where AI was central to the solution, not an add-on.

💵 Compensation & Benefits

Salary Range: $249,600 - $312,000 annually.

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 per year

• Holiday Break between December 25th and December 31st

• Flexible Paid Time Off (PTO)

• Employee Assistance Program (EAP)

• Training and professional development opportunities

Working Hours: While not explicitly stated, a 40-hour work week is standard for full-time roles. Given the on-site requirement and the leadership nature of the role, flexibility may be expected to meet project deadlines and team needs.

📝 Enhancement Note: The salary range provided is competitive for a Design Director role in San Francisco, especially within a Series D tech company. The extensive benefits package reflects a commitment to employee well-being and professional growth, which is attractive to senior talent. The "Work-from-Home Stipend" and "Therapy Reimbursement" are particularly relevant in the current work environment and for a company focused on mental healthcare. The San Francisco location also implies a high cost of living, which the salary range aims to address.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Technology (specifically focusing on mental healthcare access and provider enablement). Headway is disrupting the traditional mental healthcare system by addressing the significant barrier of insurance, making care more accessible and affordable.

Company Size: The description mentions "Series D company with $325M+ in funding," indicating a significant growth stage with a substantial workforce, likely ranging from 200-500+ employees, and potentially growing rapidly. This size suggests a dynamic environment with established processes but still retaining startup agility.

Founded: Founded with a mission to fix mental healthcare access, Headway is a relatively young company that has achieved rapid growth and significant funding, implying a culture of innovation, speed, and impact.

Team Structure:

• The design team is described as "AI-first," indicating a forward-thinking approach and a significant investment in leveraging AI for product development.

• Designers are expected to work closely with Product and Engineering, suggesting a highly collaborative, integrated structure common in agile tech organizations.

• The role of Design Director implies a reporting structure where this individual will manage a team of designers and likely report to a VP of Product, Head of Design, or CTO.

• Cross-functional collaboration is a core tenet, with designers expected to partner across departments to define vision and drive execution. Methodology:

• AI-Native Product Development: A core methodology is the proactive integration of AI into product design and development, using tools like Claude, Cursor, and MagicPatterns to prototype and build features.

• User-Centric Design: Direct engagement with providers and patients is crucial for validating solutions and ensuring the product meets real-world needs.

• Agile Development: The hyper-growth startup environment and emphasis on rapid iteration suggest an agile development methodology, with designers deeply embedded in product teams.

• Data-Driven Decisions: While not explicitly stated, the nature of operations-focused roles and a company of this scale typically relies on data analytics to inform product decisions and measure success.

Company Website: https://headway.co/

📝 Enhancement Note: Headway's mission is central to its culture, attracting individuals passionate about improving mental healthcare access. The "AI-first" design team is a key differentiator, suggesting a culture that embraces cutting-edge technology and encourages experimentation. The company's stage (Series D) implies a balance between established processes and the fast-paced, innovative spirit of a growing startup.

📈 Career & Growth Analysis

Operations Career Level: This role is at a senior leadership level, specifically a Design Director. It involves managing a team, setting strategic direction for a significant product area (Provider EHR experience), and directly influencing the company's product roadmap and technological approach (AI-native design). The scope includes both people leadership and hands-on contribution in a "player-coach" capacity.

Reporting Structure: The Design Director will likely report to a VP of Product, Head of Design, or potentially a Chief Product Officer, depending on the company's specific organizational structure. They will manage a team of product designers and work in close partnership with Product Managers and Engineering Leads.

Operations Impact: This role has a profound impact on Headway's core mission by shaping the daily operating system for tens of thousands of mental health providers. By making the EHR experience intuitive, efficient, and AI-powered, the design team directly contributes to provider satisfaction, retention, and the overall scalability of Headway's platform. This, in turn, enables more patients to access affordable mental healthcare, directly aligning with the company's mission and business objectives.

Growth Opportunities:

• Leadership Development: Significant opportunity to hone people management skills, refine strategic vision setting, and potentially grow into a Head of Design or VP of Product role as the company scales.

• AI Design Specialization: Deepen expertise in AI-native product design and AI-assisted workflows, becoming a thought leader in this emerging field within the health tech space.

• Cross-functional Influence: Gain experience influencing organizational direction and product strategy at a high level, working across multiple departments to drive innovation.

• Product Expansion: Contribute to the design of new AI-driven features and potentially expand the scope of the EHR experience to encompass new functionalities or integrations.

• Industry Impact: Play a key role in transforming mental healthcare delivery through technology, making a tangible difference in the lives of providers and patients.

📝 Enhancement Note: This is a high-impact leadership role offering substantial growth potential, particularly for those interested in shaping the future of AI in healthcare. The "player-coach" model allows for continued hands-on design contribution while developing leadership skills, making it attractive for experienced designers looking to move into management or for existing managers seeking a more innovative environment.

🌐 Work Environment

Office Type: The job is listed as On-site in San Francisco, CA. This suggests a physical office location where team members are expected to work. While the description doesn't detail the office setup, companies like Headway, especially at this stage, often provide modern, collaborative workspaces.

Office Location(s): San Francisco, California - a major hub for technology companies, offering access to talent and resources. Specific office details would need to be confirmed, but it is likely a modern office space designed to foster collaboration.

Workspace Context:

• Collaborative Environment: The emphasis on cross-functional collaboration and the "AI-first" design team suggests an environment where designers, product managers, and engineers work closely together, likely in open-plan or shared workspace settings.

• Technology Access: As an AI-native company, expect access to cutting-edge design and development tools, including powerful hardware and software for AI prototyping and development.

• Team Interaction: The on-site requirement facilitates direct interaction, spontaneous brainstorming, and stronger team cohesion, which is crucial for complex design challenges and managing a team.

Work Schedule: The role is full-time, with an expected 40-hour work week. However, leadership roles in hyper-growth companies often require flexibility and dedication beyond standard hours, especially to meet critical deadlines or drive strategic initiatives. The company offers flexible PTO, indicating a balance between demanding work and personal time.

📝 Enhancement Note: The on-site requirement in San Francisco suggests a dynamic, collaborative office setting. For operations professionals, this means being part of a physical team, fostering direct communication and innovation, and having access to company resources. The flexibility within a structured work week allows for managing complex projects and personal needs.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter will likely conduct an initial screening call to assess basic qualifications, experience alignment, and cultural fit. Be prepared to discuss your leadership philosophy and experience with B2B SaaS and AI design.

• Hiring Manager Interview: A conversation with the hiring manager (likely the Head of Design or VP of Product) to delve deeper into your experience, leadership style, strategic thinking, and approach to AI-native design.

• Portfolio Presentation & Design Challenge: A crucial stage where you will present your portfolio, showcasing key projects and your process. This may be combined with or followed by a design challenge, which could involve critiquing an existing experience, proposing solutions for a given problem, or outlining an AI-driven workflow. Expect to discuss your use of AI tools and design systems.

• Team Interviews: Meetings with potential direct reports (designers) and cross-functional partners (Product Managers, Engineering Leads) to assess collaboration style, team dynamics fit, and ability to influence.

• Senior Leadership Interview: A final interview with senior leadership (e.g., CTO, CEO) to discuss your strategic vision, alignment with Headway's mission, and overall leadership potential.

Portfolio Review Tips:

• Highlight AI Integration: Clearly showcase projects where AI was integral to the solution, detailing your specific role in leveraging AI tools and how it enhanced the design outcome.

• Demonstrate Leadership: Include case studies where you led design initiatives, managed teams, and influenced product strategy. Emphasize your "player-coach" approach.

• Showcase B2B SaaS Expertise: Present complex B2B SaaS projects that highlight your understanding of enterprise user needs, scalability, and consumer-grade UX.

• Detail Your Process: For each project, explain your design process, including user research, problem definition, ideation, prototyping (especially with AI tools), iteration, and impact measurement.

• Quantify Impact: Whenever possible, use metrics to demonstrate the success of your designs, such as improvements in user efficiency, task completion rates, or provider satisfaction.

• Structure for Clarity: Organize your portfolio logically, perhaps by theme or project type, and be prepared to walk through your most relevant work concisely and compellingly.

Challenge Preparation:

• Understand AI-Native Design: Familiarize yourself with current trends and best practices in AI-driven product design. Be ready to discuss how AI can transform existing workflows.

• Provider Workflow Research: If possible, research common workflows and pain points for mental health providers using EHR systems. This will help you tailor your responses to the specific context of Headway.

• AI Tool Proficiency: Be prepared to discuss your experience with AI prototyping tools like Claude, Cursor, and MagicPatterns, and how you would integrate them into a design workflow.

• Strategic Thinking: Practice articulating your vision for an AI-native practice management experience and how you would lead a team to achieve it.

• Communication Skills: Focus on clear, concise communication, especially when presenting your portfolio and discussing design decisions.

📝 Enhancement Note: The application process emphasizes practical application of AI in design and strong leadership skills. Candidates should be ready to not only present their past work but also discuss their forward-thinking approach to AI-driven product development and team management. The portfolio review will be a critical juncture, requiring a clear demonstration of how AI has been integrated into their design process and outcomes.

🛠 Tools & Technology Stack

Primary Tools:

• AI Prototyping & Development: Claude, Cursor, MagicPatterns (explicitly mentioned as required for designers).

• Design & Prototyping: Figma, Sketch, Adobe Creative Suite (standard industry tools, assumed).

• User Research Platforms: UserTesting.com, Lookback, Maze, or similar for remote user feedback and testing.

• Design System Management: Tools integrated with design software to manage component libraries and documentation.

Analytics & Reporting:

• Product Analytics: Amplitude, Mixpanel, Google Analytics (for understanding user behavior within the EHR and patient platforms).

• Data Visualization: Tableau, Looker, or similar for creating dashboards to track key performance indicators (KPIs) related to provider experience and platform adoption.

CRM & Automation:

• CRM: Salesforce, HubSpot (likely used internally for sales and marketing, but understanding CRM principles is beneficial).

• Project Management: Jira, Asana, Trello (for managing design tasks, sprints, and cross-functional projects).

• Collaboration Tools: Slack, Microsoft Teams (for day-to-day communication and team coordination).

📝 Enhancement Note: The explicit mention of AI tools like Claude, Cursor, and MagicPatterns is a critical differentiator. Candidates should highlight their proficiency and experience with these specific technologies. Familiarity with standard B2B SaaS design and development tools is also expected.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to improving mental healthcare access and making therapy affordable. This is the core value that drives the company's work.

• AI-Native Innovation: Embracing AI as a fundamental tool for product design and development, fostering a culture of experimentation and pushing technological boundaries.

• User-Centricity: Deep empathy for both providers and patients, with a continuous effort to understand and address their needs through intuitive and effective design.

• Excellence & Craft: A commitment to high standards in design quality, user experience, and overall product execution.

• Collaboration & Transparency: Working effectively across teams, sharing knowledge, and maintaining open communication to achieve shared goals.

Collaboration Style:

• Integrated Teams: Designers are embedded within product and engineering teams, working closely on a daily basis.

• Player-Coach Model: Leaders are expected to both guide and contribute directly, fostering a hands-on, collaborative approach to problem-solving.

• Cross-functional Partnership: Strong relationships with Product Management and Engineering are essential for defining strategy, iterating on designs, and ensuring successful implementation.

• Feedback Culture: An environment that encourages constructive feedback and open dialogue to continuously improve both the product and team processes.

📝 Enhancement Note: The culture is characterized by a strong mission, a pioneering approach to AI in design, and a collaborative, user-focused environment. For operations professionals, this means being part of a team that is passionate about its impact and innovative in its methods.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling an AI-Native Design Practice: Building and scaling a design team and its processes to effectively leverage AI for a complex B2B SaaS product in a rapidly evolving market.

• Balancing Innovation with Usability: Ensuring that cutting-edge AI features enhance, rather than complicate, the provider experience, maintaining a high standard of usability and intuitiveness.

• Cross-Functional Alignment: Navigating the complexities of aligning design vision with product and engineering roadmaps, especially in a fast-paced, hyper-growth environment.

• Provider Adoption of AI Tools: Educating and encouraging providers to adopt new AI-powered workflows within their daily practice.

• Maintaining Design Coherence: Ensuring a seamless and integrated user experience across the provider EHR, patient-facing interfaces, and marketplace functionalities as the platform grows.

Learning & Development Opportunities:

• AI Design Leadership: Becoming a leader in the emerging field of AI-driven product design and development within the healthcare sector.

• Strategic Product Influence: Gaining deep experience in shaping product strategy and influencing organizational direction for a high-growth tech company.

• Team Building & Mentorship: Developing advanced people management and team-building skills by leading and mentoring a talented design team.

• Industry Expertise: Deepening knowledge of the mental healthcare landscape and the operational challenges faced by providers.

• Advanced Design Methodologies: Exploring and implementing novel design and prototyping techniques leveraging AI to solve complex user problems.

📝 Enhancement Note: The role presents significant opportunities for growth, particularly in the specialized area of AI-driven design leadership. Candidates will be challenged to innovate and scale while contributing to a meaningful mission.

💡 Interview Preparation

Strategy Questions:

• "How would you define and drive the vision for an AI-native EHR experience for mental health providers, considering their unique workflows and challenges?"

• "Describe a time you had to balance aggressive timelines with maintaining high design quality. What was your approach, and how did you leverage your team?"

• "How do you ensure design coherence across different product platforms and user journeys (e.g., provider EHR, patient portal, marketplace)?"

• "Walk me through how you would use AI tools like Claude or Cursor to prototype and iterate on a new feature for our EHR. What are the benefits and potential pitfalls of this approach?" Company & Culture Questions:

• "What excites you most about Headway's mission to fix mental healthcare access, and how does this align with your own values?"

• "How would you foster a culture of innovation and high craft within your design team, especially in an AI-first environment?"

• "Describe your experience working with Product Managers and Engineers. How do you build strong collaborative relationships to drive product success?"

• "What are your thoughts on the role of design in a Series D hyper-growth startup?" Portfolio Presentation Strategy:

• Narrative Arc: Structure your portfolio presentation with a clear narrative for each project: problem, your role, the process (emphasizing AI use), the solution, and the quantifiable impact.

• Focus on Leadership: Highlight instances where you led design initiatives, managed teams, and influenced strategic decisions.

• Demonstrate "Player-Coach" Capability: Show examples of both strategic leadership and hands-on design execution, particularly with AI tools.

• Quantify Outcomes: Use data and metrics to demonstrate the success and business impact of your design work.

• Engage Your Audience: Be prepared to answer in-depth questions about your design choices, process, and leadership philosophy. Make it interactive.

📝 Enhancement Note: Interview preparation should focus on demonstrating leadership, strategic thinking, and a deep understanding of AI-driven design. Candidates should be ready to articulate their vision for the Provider EHR experience and showcase their ability to lead a team in an innovative, mission-driven environment.

📌 Application Steps

To apply for this Design Director position:

• Submit your application through the official Headway careers page: https://headway.co/careers or the provided Ashby link.

• Tailor Your Resume: Highlight experience in Design Leadership, B2B SaaS, AI-native product design, and team management. Use keywords from the job description to ensure ATS compatibility.

• Curate Your Portfolio: Select projects that best showcase your leadership, strategic thinking, hands-on design skills with AI tools, and experience with complex SaaS platforms.

• Prepare Your Presentation: Practice presenting your portfolio concisely, focusing on your process, AI integration, and impact. Be ready to discuss your leadership philosophy.

• Research Headway: Understand the company's mission, product, funding, and recent developments. Prepare thoughtful questions to ask the interviewers about the company and the role.

⚠️ 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.