Design Director, Provider Experience

📍 Job Overview

Job Title: Design Director, Provider Experience

Company: Headway

Location: New York, New York, United States; San Francisco, California, United States; Seattle, Washington, United States

Job Type: Full-Time

Category: Product Design / UX Leadership

Date Posted: 2026-06-04T22:13:26

Experience Level: 5-10 Years

Remote Status: Hybrid

🚀 Role Summary

• Lead the strategic vision and execution for Headway's Provider Electronic Health Record (EHR) experience, focusing on AI-native practice management solutions.

• Drive the design of AI-augmented workflows across scheduling, clinical documentation, session delivery, and client engagement within the EHR platform.

• Build, mentor, and manage a high-performing team of designers, fostering a culture of craft excellence and innovation.

• Act as a player-coach, contributing hands-on to key design initiatives while elevating the team's overall output and quality.

• Ensure seamless integration and design coherence across provider-facing EHR features, patient journeys, and marketplace capabilities.

📝 Enhancement Note: This role is positioned as a senior design leadership position with a strong emphasis on AI-driven product development within the healthcare technology sector. The "Provider Experience" focus indicates a deep dive into the needs of mental health professionals using Headway's platform, aiming to make it the de facto practice management solution. The AI-native aspect is critical, requiring a candidate comfortable with leveraging AI tools for design and development.

📈 Primary Responsibilities

• Define and champion the long-term strategy and vision for the provider EHR experience, collaborating closely with Product, Engineering, and senior leadership to conceptualize an AI-first practice management ecosystem.

• Recruit, onboard, and develop a talented team of product designers, setting rigorous craft standards and providing coaching to ensure consistent delivery of high-quality user experiences.

• Take ownership of critical design initiatives, acting as a hands-on contributor to prototyping, user flow design, and interaction patterns, particularly for AI-powered features.

• Maintain design consistency and coherence across the entire provider and patient journey, ensuring seamless transitions between EHR functionalities, patient search, booking, and onboarding processes.

• Utilize AI-powered design tools (e.g., Claude, Cursor, MagicPatterns) for rapid prototyping, iteration, and the development of information architecture (IA) and user flows.

• Collaborate with Product and Engineering to validate AI-generated designs and determine optimal paths for production deployment.

• Conduct user research, directly engaging with mental health providers to gather insights, validate design concepts, and ensure solutions meet real-world needs.

• Actively contribute to the growth of Headway's design system and foster a collaborative design culture by sharing AI best practices, prompts, and reusable patterns.

📝 Enhancement Note: The responsibilities highlight a dual focus on strategic leadership and hands-on design execution. The emphasis on AI tools like Claude and Cursor suggests an expectation for designers to be early adopters and proficient users of emerging AI technologies in the design and development lifecycle. The need to connect provider EHR with patient-side flows and marketplace capabilities indicates a holistic product ownership approach.

🎓 Skills & Qualifications

Education: Bachelor's or Master's degree in Design, Human-Computer Interaction, Computer Science, or a related field, 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 in hyper-growth startup environments (Series C+) and larger, more mature organizations is highly valued.

Required Skills:

• Proven experience in Design Leadership, including team management, mentorship, and fostering a strong design culture.

• Expertise in designing for complex B2B SaaS platforms with a commitment to high-quality, intuitive user experiences.

• Demonstrated ability to conceptualize and design AI-native or AI-augmented product experiences, rethinking workflows around AI capabilities.

• Strong command of Product Strategy and the ability to translate business goals into actionable design roadmaps.

• Proficiency in User Experience (UX) Design principles and methodologies.

• Hands-on experience with Prototyping tools and techniques, ideally including AI-assisted tools.

• Deep understanding of Design Thinking and its application in problem-solving.

• Experience in Team Management and talent development within a design function.

• Skills in conducting and leveraging User Research to inform design decisions.

• Knowledge of Information Architecture (IA) for organizing complex digital products.

• Experience with Design Systems to ensure consistency and scalability.

• Exceptional Cross-functional Collaboration skills, working effectively with Product Management and Engineering. Preferred Skills:

• Experience specifically within the Healthcare Technology sector, understanding its unique challenges and regulatory landscape.

• Familiarity with EHR systems and healthcare practice management software.

• Experience with Agile development methodologies and working in fast-paced startup environments.

• Proficiency with AI design tools such as Claude, Cursor, and MagicPatterns.

• Portfolio showcasing successful implementation of design at scale and systematic design approaches.

📝 Enhancement Note: The experience requirement is specific about leading teams for B2B SaaS with consumer-grade UX, indicating a high bar for both leadership and craft. The emphasis on AI-native design is a key differentiator, suggesting that candidates who have already explored or implemented AI in product workflows will be strongly considered. A portfolio showcasing both individual high-craft work and systematic design at scale is essential.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate a track record of leading design initiatives from concept to launch within complex B2B SaaS environments.

• Showcase examples of designing AI-native or AI-augmented product experiences, detailing the problem, your approach, and the impact.

• Include case studies that illustrate systematic approaches to design at scale, highlighting the use of design systems and ensuring cross-functional coherence.

• Provide evidence of strategic thinking, including how you defined vision, influenced organizational direction, and partnered with Product and Engineering.

• Present examples of your leadership capabilities, such as team management, mentorship, and fostering design best practices. Process Documentation:

• Detail your process for defining product strategy and vision, including how you collaborate with stakeholders.

• Illustrate your approach to user research and how you integrate insights into the design process, especially for complex workflows like EHR.

• Explain your methodology for working with AI design tools, including prompt engineering, iterating on AI-generated outputs, and integrating them into production code.

• Document your experience in building and maintaining design systems, ensuring scalability and consistency across a growing product suite.

📝 Enhancement Note: Candidates will be expected to present a portfolio that not only showcases their individual design prowess but also their strategic leadership and ability to manage design at scale within a high-growth tech company. The AI-native aspect of the role means that the portfolio should ideally include examples of how AI was leveraged to solve design challenges or create novel user experiences.

💵 Compensation & Benefits

Salary Range: $249,600 - $312,000 USD per year (based on location, qualifications, and experience).

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: Standard full-time hours are expected, likely around 40 hours per week, with flexibility often afforded in hybrid environments.

📝 Enhancement Note: The salary range provided is competitive for senior design leadership roles in major tech hubs like New York, San Francisco, and Seattle. The comprehensive benefits package reflects a commitment to employee well-being and professional growth, which is particularly attractive for leadership positions. The "Work-from-Home Stipend" is a notable perk for a hybrid role.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology (specifically focusing on mental healthcare access and provider enablement).

Company Size: Headway is a Series D funded company, indicating significant growth and a substantial employee base, likely in the hundreds. This suggests a structured, yet still agile, organizational environment.

Founded: Headway was founded to address the significant gap in accessible mental healthcare due to insurance complexities. This mission-driven ethos is likely central to its culture.

Team Structure:

• The design team is expected to be integrated within product development squads, working closely with Product Managers and Engineers.

• As a Design Director, you will lead a team of designers focused on the Provider EHR experience, reporting into a higher-level design leader or potentially a VP of Product/Design.

• Cross-functional collaboration is key, with regular interaction with leadership, product strategy, and engineering teams to align on vision and execution. Methodology:

• Headway emphasizes an AI-first approach to product development, integrating AI tools throughout the design and engineering process.

• The company likely employs Agile methodologies for iterative product development and rapid deployment.

• A strong focus on user-centric design, using research and direct provider feedback to inform product decisions.

• Emphasis on building scalable systems and design foundations to support rapid growth.

Company Website: https://www.headway.co/

📝 Enhancement Note: Headway's mission to improve mental healthcare access is a strong cultural anchor. The "AI-first" methodology is a defining characteristic, suggesting a culture that embraces innovation and cutting-edge technology. The company's stage (Series D) implies a dynamic environment with opportunities for significant impact.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior leadership position within the product design function, specifically focused on a critical area of the platform (Provider EHR). It's a strategic role with significant influence over product direction and team development.

Reporting Structure: The Design Director will likely report to a VP of Design, Head of Product, or a similar senior executive. They will, in turn, manage a team of individual contributor designers. This position bridges strategic vision with day-to-day execution.

Operations Impact: The Provider EHR experience is the core operational tool for tens of thousands of mental health providers on Headway's platform. Directly improving this experience has a profound impact on provider efficiency, patient care delivery, and ultimately, Headway's ability to scale its mission. Designing an AI-native system can dramatically improve operational workflows, reduce administrative burden, and enhance the quality of care.

Growth Opportunities:

• Leadership Advancement: Potential to grow into a VP of Design or Head of Design role as the company scales.

• Strategic Influence: Opportunity to shape the future of AI in healthcare practice management and influence broader company strategy.

• Team Building: Experience in building and scaling a high-performing design team in a fast-growing company.

• Domain Expertise: Deepen expertise in healthcare technology, AI applications, and B2B SaaS product development.

• Innovation: Lead the charge in pioneering AI-native design solutions that set industry standards.

📝 Enhancement Note: This role offers a clear path for growth into higher levels of design leadership, with opportunities to influence product strategy significantly. The emphasis on AI and healthcare makes it a highly relevant and future-forward career move.

🌐 Work Environment

Office Type: Headway operates on a hybrid work model, meaning employees will have the opportunity to work from designated office locations in New York, San Francisco, or Seattle, as well as remotely. This suggests a flexible approach to work arrangements.

Office Location(s):

• New York, New York, United States

• San Francisco, California, United States

• Seattle, Washington, United States

These are major tech hubs, offering access to talent and a vibrant professional community.

Workspace Context:

• The hybrid model promotes collaboration during in-office days while allowing for focused work remotely.

• Expect a dynamic, fast-paced startup environment where cross-functional teams collaborate closely.

• Access to modern design tools and technology, including AI-powered platforms, will be standard.

• The culture likely encourages open communication, idea sharing, and continuous learning.

Work Schedule: While specific hours are not detailed, a standard full-time schedule (approximately 40 hours per week) is implied. The hybrid nature allows for some flexibility in managing work hours, balanced with in-office collaboration needs.

📝 Enhancement Note: The hybrid model offers a balance between in-person collaboration and remote flexibility, a common setup for growing tech companies. The specified locations are prime tech markets, suggesting a strong talent pool and established infrastructure.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter will likely review your application and conduct an initial call to assess basic qualifications and cultural fit.

• Hiring Manager Interview: A conversation with the hiring manager (likely a VP of Design or Head of Product) to discuss your experience, leadership style, and strategic thinking.

• Portfolio Review & Design Challenge: A session where you present your portfolio, focusing on relevant case studies, and potentially tackle a design challenge related to AI-native EHR experiences.

• Cross-functional Interviews: Meetings with key stakeholders from Product Management and Engineering to assess collaboration skills and technical understanding.

• Final Round: Potentially a discussion with senior leadership to finalize the decision.

Portfolio Review Tips:

• Curate Strategically: Focus on 2-3 projects that best demonstrate your experience in B2B SaaS, AI-driven design, and leadership.

• Tell a Story: For each case study, clearly articulate the problem, your role, the process (especially AI usage), key decisions, and measurable outcomes.

• Highlight AI Integration: Explicitly show how you used AI tools (Claude, Cursor, MagicPatterns) to prototype, iterate, or solve problems. Detail the prompts, the AI outputs, and how you refined them.

• Showcase Leadership: Include examples of how you've led teams, mentored designers, influenced strategy, and collaborated across functions.

• Quantify Impact: Use metrics whenever possible to demonstrate the business impact of your design work (e.g., increased provider efficiency, improved adoption rates, reduced support tickets).

Challenge Preparation:

• Understand Headway's Mission: Be prepared to discuss how design can support their goal of making mental healthcare accessible.

• Research AI in Design: Familiarize yourself with current trends and best practices in AI-assisted design workflow.

• Practice Presenting: Rehearse your portfolio presentation to ensure clarity, conciseness, and impact within the allotted time.

• Think Systemically: Consider how your design decisions impact the broader ecosystem (patient experience, marketplace, backend operations).

📝 Enhancement Note: The interview process is designed to evaluate not only design skills but also leadership capabilities, strategic thinking, and proficiency with emerging AI technologies. A well-prepared portfolio that specifically addresses the AI-native requirement will be crucial.

🛠 Tools & Technology Stack

Primary Tools:

• AI Design Tools: Claude, Cursor, MagicPatterns (expected to be heavily utilized for prototyping and development).

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

• Design Systems: Experience with building, maintaining, and scaling design systems.

Analytics & Reporting:

• Familiarity with product analytics tools (e.g., Amplitude, Mixpanel) to track user behavior and measure design impact.

• Experience in translating data insights into design improvements. CRM & Automation:

• While not directly managing CRM, understanding how design impacts provider workflows that interact with practice management and billing systems (akin to CRM functions for providers) is important.

• Awareness of automation principles in workflow design.

📝 Enhancement Note: Proficiency with AI-powered design and development tools like Claude and Cursor is a key differentiator for this role. Candidates should be prepared to discuss their experience and comfort level with these emerging technologies.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to improving mental healthcare access and provider experience.

• AI-First Innovation: Embracing cutting-edge AI technologies to redefine product experiences.

• User-Centricity: Deep empathy for providers and a focus on solving their real-world problems.

• Collaboration & Transparency: Open communication and close partnership across Product, Engineering, and Design.

• High Craft & Quality: Striving for excellence in user experience and design execution.

• Impact & Ownership: Taking responsibility for driving meaningful outcomes and making a significant contribution.

Collaboration Style:

• Designers are expected to be embedded within product teams, fostering close collaboration with Product Managers and Engineers.

• A player-coach model means leaders are both guiding the team and actively contributing to design work.

• Emphasis on sharing knowledge, best practices, and learning from each other, especially regarding AI workflows.

• Regular feedback loops and design critiques are likely part of the process.

📝 Enhancement Note: The company culture appears to value both a strong sense of purpose and a forward-thinking, technology-driven approach. Expect a collaborative environment where individual contributions are recognized, and collective success is paramount.

⚡ Challenges & Growth Opportunities

Challenges:

• AI Integration Complexity: Seamlessly integrating AI into existing complex workflows (EHR) while ensuring reliability, usability, and ethical considerations.

• Balancing Leadership and Craft: Effectively managing a design team while remaining hands-on with strategic design initiatives.

• Scaling Design Systems: Ensuring design consistency and efficiency across a rapidly growing platform and evolving feature set.

• Cross-Functional Alignment: Maintaining alignment on vision and execution across multiple departments in a fast-paced environment.

• Provider Adoption: Encouraging adoption of new, AI-powered workflows by a diverse range of mental health professionals.

Learning & Development Opportunities:

• AI Design Leadership: Become a leader in applying AI to product design and development within the healthcare tech space.

• Mentorship & Team Building: Develop skills in coaching and growing a high-performing design team.

• Strategic Product Influence: Gain experience in shaping product strategy at a rapidly scaling, mission-driven company.

• Healthcare Tech Expertise: Deepen knowledge of the healthcare industry's challenges and opportunities.

• Industry Conferences & Training: Opportunities for professional development, attending relevant conferences, and pursuing certifications.

📝 Enhancement Note: This role offers significant challenges that are also rich with growth potential. Successfully navigating the complexities of AI integration and team leadership will be key to career advancement.

💡 Interview Preparation

Strategy Questions:

• "Describe your philosophy for leading design teams, particularly in a hybrid environment and a hyper-growth startup."

• "Walk us through a time you redefined a complex B2B SaaS workflow using AI. What was your process, and what were the outcomes?"

• "How do you ensure design coherence across different product pillars (e.g., provider EHR, patient experience, marketplace)?"

• "What's your approach to balancing hands-on design work with team management responsibilities?"

• "How would you leverage AI tools like Claude or Cursor to accelerate the design process for an EHR feature like session note generation?" Company & Culture Questions:

• "What excites you about Headway's mission to improve mental healthcare access?"

• "How do you foster a culture of design excellence and continuous learning within a team?"

• "Describe your experience working with Product and Engineering teams. How do you ensure strong collaboration?"

• "How do you approach user research and incorporate provider feedback into your design decisions?" Portfolio Presentation Strategy:

• Introduction: Briefly introduce Headway's mission and the critical role of the Provider EHR.

• Project Selection: Choose 2-3 projects demonstrating leadership, AI integration, B2B SaaS design, and a systematic approach.

• Structure Each Case Study:

  • Problem: Clearly define the user/business problem.
  • Your Role & Team: Specify your leadership responsibilities and how you collaborated.
  • Process & AI Usage: Detail your design methodology, emphasizing how AI tools were used for prototyping, ideation, or iteration. Show examples of prompts and AI outputs.
  • Solutions: Present the final designs, explaining key decisions.
  • Impact: Quantify results where possible (e.g., efficiency gains, adoption rates).

• Design System & Scalability: Discuss how your work contributes to or leverages design systems for scalability.

• Q&A: Be prepared for deep dives into your decision-making process and leadership style.

📝 Enhancement Note: Interviews will heavily focus on leadership, strategic thinking, and practical application of AI in design. Be ready to demonstrate your ability to lead a team while being a hands-on contributor, especially with AI tools.

📌 Application Steps

To apply for this operations position:

• Submit your application through the official Headway careers page.

• Tailor Your Resume: Highlight experience in Design Leadership, B2B SaaS UX, AI-driven product design, and team management. Use keywords from the job description.

• Curate Your Portfolio: Select projects that best showcase your experience with complex platforms, AI integration, and strategic design thinking. Ensure clear case studies with measurable impact.

• Prepare for AI Discussions: Be ready to articulate your experience with AI design tools and how you envision using them to enhance the Provider EHR.

• Research Headway: Understand their mission, product, and recent developments to articulate your interest and alignment with their values.

• Practice Presentation: Rehearse presenting your portfolio and answering potential interview questions, focusing on clarity, impact, and leadership.

⚠️ 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.