Senior / Staff Product Designer - Patient

📍 Job Overview

Job Title: Senior / Staff Product Designer - Patient

Company: Headway

Location: New York, New York, United States

Job Type: FULL_TIME

Category: Product Design / Healthcare Technology

Date Posted: 2026-08-14

Experience Level: 5+ Years (Senior), 8+ Years (Staff)

Remote Status: Remote (US-Based)

🚀 Role Summary

• Own the end-to-end patient product experience, driving innovation from problem framing through launch and iteration within an AI-native environment.

• Leverage cutting-edge AI tools like Claude Code and Cursor for rapid prototyping, ideation, and code-based iteration, treating AI as a core part of the design practice.

• Collaborate closely with Product Managers, Engineers, and Researchers to define product strategy, shape the roadmap, and ensure successful execution of patient-facing features.

• Design critical patient journey touchpoints, including provider discovery, insurance benefit understanding, appointment booking, and ongoing care engagement, with a focus on measurable outcomes.

• Drive a culture of experimentation, using data and clear success metrics to validate design decisions and iterate on features for improved conversion, retention, and task completion.

📝 Enhancement Note: This role is specifically for Product Designers focused on the patient experience within a healthcare technology company. The emphasis on an "AI-native" environment and prototyping in code is a significant differentiator, requiring candidates to be proficient with AI tools as a primary aspect of their workflow. The distinction between Senior and Staff levels highlights the need for leadership, mentorship, and strategic influence at the Staff level, particularly in shaping AI-native patient experiences and mentoring other designers.

📈 Primary Responsibilities

• Lead the design strategy and execution for patient-facing products, ensuring a seamless and accessible experience across the entire care journey.

• Develop and implement AI-powered patient experiences, including conversational flows, intelligent matching algorithms, and agentic care navigation solutions.

• Translate complex user needs and business requirements into intuitive and effective design solutions, utilizing advanced prototyping techniques with AI tools.

• Conduct user research, usability testing, and A/B experiments to gather insights and validate design hypotheses, directly impacting key performance indicators.

• Contribute to and evolve Headway's design system, "Helix," ensuring consistency, scalability, and efficiency across patient product surfaces.

• Mentor and guide junior designers, fostering a collaborative environment that encourages innovation, craft excellence, and AI-native design practices.

• Partner with cross-functional teams to influence product direction, prioritize initiatives, and articulate design rationale based on user insights, data, and strategic objectives.

• Own the quality bar for AI-generated design outputs, ensuring they meet high standards for usability, accessibility, and business impact.

📝 Enhancement Note: The responsibilities clearly delineate the dual focus on direct ownership of patient experience and leadership/mentorship for Staff-level candidates. The emphasis on AI-native workflows, agentic care navigation, and the "Helix" design system are critical operational components for this role.

🎓 Skills & Qualifications

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

Experience:

• Senior: 5+ years of professional product design experience, with a demonstrated track record of owning complex product surfaces end-to-end and delivering measurable business impact.

• Staff: 8+ years of professional product design experience, with a proven ability to lead both 0→1 product initiatives and at-scale product optimization, and to influence broader design team practices.

Required Skills:

• Product Design Craft: Exceptional visual design, interaction design, and user experience design skills, with a strong portfolio showcasing complex problem-solving and execution.

• AI-Native Prototyping: Proven fluency and practical experience with AI prototyping tools (e.g., Claude Code, Cursor) for generating code, prototypes, and design assets.

• Systems Thinking: Ability to design coherent and simple experiences for complex, state-heavy problems, considering the full patient journey and backend implications.

• User Research & Experimentation: Experience conducting user research, running A/B tests, and leveraging data to inform design decisions and measure impact (conversion, retention, task completion).

• Cross-functional Collaboration: Demonstrated ability to partner effectively with Product Managers, Engineers, and Researchers to shape product strategy and roadmap.

• Product Strategy Acumen: Ability to bring a strong point of view to the product roadmap, translating customer insights into actionable design strategies.

• Design Systems: Experience contributing to or utilizing design systems for maintaining consistency and scalability.

• Mission Alignment: Strong motivation and passion for Headway's mission to make mental healthcare accessible and affordable.

Preferred Skills:

• Experience designing for consumer-facing or patient-facing products in the healthcare industry.

• Experience designing agentic or AI-powered workflows, conversational interfaces, or intelligent recommendation systems.

• Experience leading design initiatives from concept (0→1) to launch and iteration.

• Mentorship experience, with a track record of elevating the craft and practices of other designers.

• Fluency in designing for complex, stateful, multi-actor experiences.

📝 Enhancement Note: The required skills are heavily weighted towards practical application of AI in the design process, systems thinking for complex healthcare workflows, and data-driven validation. The distinction between Senior and Staff is clear in the experience years and the expectation of leadership, mentorship, and 0→1 product experience for Staff level.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 2-3 detailed case studies demonstrating end-to-end product design ownership, from problem definition to shipped product and iteration.

• Highlight projects that involved complex user journeys, preferably in consumer-facing or healthcare contexts.

• Clearly articulate your role and contributions within each project, especially in collaborative environments.

• Emphasize structured thinking, problem-solving methodologies, and how you translated insights into design decisions.

• Demonstrate measurable business impact or user outcome improvements, with specific metrics and data-driven validation.

• Include examples of your work with AI prototyping tools, showcasing how you leveraged AI to accelerate ideation, prototyping, or code generation. Process Documentation:

• Case studies should detail your process for user research, ideation, prototyping (including AI-assisted methods), user testing, and iteration.

• Clearly outline how you collaborated with PMs, Engineers, and Researchers throughout the design lifecycle.

• Explain your approach to defining success metrics and how you used data to iterate on designs.

• For Staff-level candidates, include examples of how you've influenced product direction or mentored other designers through process improvements or sharing best practices.

• Showcase contributions to design systems or the development of reusable patterns.

📝 Enhancement Note: The portfolio requirements are highly specific, demanding evidence of AI tool usage in the design process, measurable impact, and detailed documentation of the design lifecycle. For Staff, the portfolio should also reflect leadership and strategic influence.

💵 Compensation & Benefits

Salary Range:

• Senior: $180,000 - $225,000 USD per year (Base Salary)

• Staff: $212,000 - $265,000 USD per year (Base Salary)

Benefits:

• Equity compensation (stock options/grants)

• Comprehensive Medical, Dental, and Vision coverage

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

• 401K retirement savings plan

• Work-from-Home Stipend for home office setup

• Therapy Reimbursement to support mental well-being

• 16 weeks of paid 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) policy

• Employee Assistance Program (EAP) for confidential support

• Generous budget for Training and professional development opportunities

Working Hours: Standard full-time work week, typically 40 hours. The company promotes a flexible approach to work schedules, encouraging autonomy and results-oriented performance within the remote work setting.

📝 Enhancement Note: The salary ranges are explicitly provided for both Senior and Staff levels, reflecting a significant difference in compensation expectations. The benefits package is extensive, with specific mentions of therapy reimbursement, fertility support, and a substantial parental leave policy, all highly relevant to employee well-being and work-life balance. The work hours are standard but accompanied by a note on flexibility.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology / Mental Health Services

Company Size: Series D company with significant growth; likely 200-500 employees based on funding stage.

Founded: Headway was founded to address the critical gap in accessible mental healthcare, aiming to build a new system where insurance is a viable payment method for mental health services.

Team Structure:

• The design team operates with a high degree of autonomy and collaboration, integrated into product squads alongside PMs and Engineers.

• Designers are expected to be proactive, taking ownership of their respective product areas.

• A strong emphasis is placed on cross-functional partnership and shared ownership of outcomes.

• For Staff Designers, there's an expectation of mentorship and contributing to the growth and direction of the broader design organization. Methodology:

• AI-First Design: The core methodology involves treating AI as an integral tool for design, from ideation and prototyping to potentially code generation.

• Data-Driven Iteration: Decisions are heavily influenced by experimentation, A/B testing, and analysis of user behavior metrics (conversion, retention).

• Customer Obsession: Deep understanding of patient needs and challenges is paramount, driving the design of empathetic and effective solutions.

• Agile Development: The product development process likely follows agile principles, enabling rapid iteration and adaptation.

Company Website: https://headway.co/

📝 Enhancement Note: The company culture is portrayed as mission-driven, innovative, and collaborative, with a strong emphasis on leveraging AI and data to solve significant problems in mental healthcare accessibility. The size and funding stage suggest a dynamic, fast-paced environment with opportunities for impact.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior-to-principal individual contributor track within Product Design, focusing on high-impact patient experience ownership.

• Senior: Expected to independently own complex product areas, drive significant feature development, and contribute to product strategy.

• Staff: Expected to lead ambiguous, large-scale initiatives, define new product areas (0→1), mentor other designers, and influence the design organization's practices and direction.

Reporting Structure: Designers typically report into a Head of Design or Design Lead, who is part of the broader product leadership team. They work within cross-functional product squads, reporting functionally to design leadership and collaboratively to product management and engineering leads for their specific initiatives.

Operations Impact: The work directly impacts patient access to mental healthcare, driving engagement, retention, and overall success of Headway's platform. The success of the patient experience is critical to Headway's mission and business growth, directly influencing provider adoption and patient utilization of services.

Growth Opportunities:

• Skill Specialization: Deepen expertise in AI-native design workflows, conversational UI, and complex healthcare patient journeys.

• Leadership Development: For Staff designers, opportunities to mentor, lead design initiatives, shape team processes, and influence product strategy.

• Career Progression: Potential to move into Principal Designer, Design Lead, or management roles within the design organization.

• Industry Impact: Contribute to a mission-critical area of healthcare technology, gaining experience in a rapidly evolving field.

• Learning & Development: Access to training, professional development budgets, and opportunities to stay at the forefront of design and AI technologies.

📝 Enhancement Note: The career path is clearly defined for both Senior and Staff levels, emphasizing individual contribution, strategic influence, and leadership growth. The impact of the role is directly tied to the company's core mission, offering significant professional fulfillment.

🌐 Work Environment

Office Type: Headway operates as a remote-first company, with a strong emphasis on supporting employees working from home. While specific office locations are not detailed for this role, the primary requirement is for US-based candidates.

Office Location(s): Primarily remote within the United States. The company is headquartered in New York, NY, but this role is designated as TELECOMMUTE.

Workspace Context:

• Remote Collaboration: The environment is built for effective remote collaboration, utilizing digital tools for communication, design, and project management.

• AI-Powered Tools: Designers have access to and are expected to utilize AI tools (Claude Code, Cursor) as part of their daily workflow.

• Cross-functional Interaction: Frequent interaction with product managers, engineers, researchers, and other designers, facilitated through virtual meetings and collaboration platforms.

• Focus on Autonomy: A culture that empowers individuals to manage their work and time effectively in a remote setting.

Work Schedule: While the standard is 40 hours per week, the remote-first nature and focus on results allow for flexibility in scheduling, accommodating different time zones within the US and personal work styles.

📝 Enhancement Note: The remote-first nature is a key aspect, supported by tools and culture designed for distributed teams. The integration of AI tools into the daily workspace is a defining characteristic of this environment.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Application review focusing on portfolio and resume, assessing alignment with experience requirements and AI-native design skills.

• Hiring Manager / Recruiter Call: Discussion about your background, motivations, and the role specifics.

• Design Challenge / Portfolio Presentation: A core part of the process will involve presenting your portfolio, likely focusing on 1-2 key case studies that demonstrate your process, craft, impact, and AI tool usage. This may include a take-home challenge or a live presentation.

• Cross-functional Interviews: Meetings with Product Managers, Engineers, and Researchers to assess collaboration style, product thinking, and technical understanding.

• Staff-Level Interview: For Staff candidates, interviews may include discussions on leadership, mentorship, strategic influence, and shaping design practices.

• Final Round: Potential final interviews with senior leadership to assess cultural fit and strategic alignment.

Portfolio Review Tips:

• Highlight AI Integration: Clearly showcase how you used AI tools in your design process, from ideation to prototyping. Provide examples of prompts, generated assets, and how AI accelerated your work.

• Focus on Impact: For each case study, clearly define the problem, your solution, your specific role, and the measurable outcomes achieved (e.g., conversion lift, retention improvement, task success rate).

• Structure Your Narrative: Tell a compelling story for each case study. Explain your thought process, the challenges you faced, and how you overcame them.

• Showcase Systems Thinking: Demonstrate your ability to design for complex systems and understand the broader implications of your design decisions.

• Tailor to the Role: Emphasize projects that are most relevant to patient-facing products, healthcare, or AI-driven experiences.

• Be Prepared for Code Prototypes: Given the AI-native requirement, be ready to discuss or even demonstrate code-based prototypes if applicable.

Challenge Preparation:

• Understand Headway's mission and the specific problem space of mental healthcare accessibility.

• Prepare to discuss your approach to designing for sensitive user needs and complex insurance/benefit landscapes.

• Practice articulating your design decisions clearly and concisely, backing them up with user data and strategic rationale.

• Be ready to discuss your experience with experimentation and how you measure design success.

• For Staff: Prepare examples of how you've mentored others, influenced product direction, or improved design processes.

📝 Enhancement Note: The interview process emphasizes practical application of AI in design and a strong portfolio review. Candidates should be prepared to demonstrate their skills with AI tools and articulate the impact of their work with data.

🛠 Tools & Technology Stack

Primary Tools:

• AI Prototyping & Development: Claude Code, Cursor, and other AI-powered coding and design assistants are central to the workflow.

• Design Software: Figma (or similar industry-standard tools like Sketch, Adobe XD) for UI design, wireframing, and prototyping.

• Prototyping Tools: Beyond AI, potentially InVision, Principle, or Framer for specific prototyping needs.

Analytics & Reporting:

• Product Analytics: Tools like Amplitude, Mixpanel, or Google Analytics for tracking user behavior, feature adoption, and conversion funnels.

• Experimentation Platforms: Tools for A/B testing and multivariate testing to validate design hypotheses.

• Data Visualization: Potentially Tableau, Looker, or internal dashboards for reporting on key metrics and communicating findings.

CRM & Automation:

• While not directly a designer's primary tool, understanding CRM principles (e.g., Salesforce, HubSpot) might be beneficial for context on user lifecycle management.

• Automation tools may be used for workflow optimization within product development, though specific tools are not listed for design. Design Systems:

• Helix: Headway's internal design system, which designers will contribute to and leverage.

📝 Enhancement Note: The explicit mention of Claude Code and Cursor as primary AI tools is a critical technical requirement. Proficiency with Figma is assumed, and familiarity with product analytics and experimentation platforms is essential for a data-driven design role.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A deep commitment to making mental healthcare accessible and affordable for everyone.

• AI-Native: Embracing AI as a fundamental tool to innovate and accelerate design and product development.

• Customer Obsession: Prioritizing the patient and provider experience, seeking to deeply understand and solve their challenges.

• Data-Informed: Relying on experimentation, metrics, and research to guide decisions and measure impact.

• Craft Excellence: Maintaining high standards for design quality, usability, and aesthetic appeal.

• Collaboration & Ownership: Fostering a culture where individuals take ownership and work effectively across teams.

• Continuous Learning: Encouraging exploration of new technologies, methodologies, and professional development.

Collaboration Style:

• Cross-functional Partnership: Designers are integrated into product teams and work hand-in-hand with PMs, Engineers, and Researchers.

• Open Communication: Encouraging transparent feedback, constructive critique, and knowledge sharing.

• Iterative & Agile: A flexible approach that embraces change and allows for rapid iteration based on learnings.

• Shared Ownership: Teams collectively own the success of their product initiatives, fostering a sense of collective responsibility.

📝 Enhancement Note: The values highlight a blend of mission-oriented purpose, technological innovation (AI), data-driven decision-making, and strong collaborative practices, all crucial for success in this role and company.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Sensitive Populations: Creating empathetic and effective experiences for individuals seeking mental health support, navigating complex emotional and logistical barriers.

• AI Integration Complexity: Mastering and effectively leveraging AI tools for design, ensuring ethical use, and maintaining a high quality bar for AI-generated outputs.

• Balancing Innovation with Scalability: Developing novel AI-native solutions while ensuring they are robust, scalable, and maintainable within a growing platform.

• Navigating Healthcare Systems: Designing for the intricacies of insurance benefits, provider networks, and regulatory landscapes within mental healthcare.

• Proving ROI of Design: Consistently demonstrating the business value and user impact of design initiatives through data and experimentation.

Learning & Development Opportunities:

• AI Design Mastery: Becoming a leader in AI-native product design, exploring cutting-edge techniques and tools.

• Healthcare Product Expertise: Deepening understanding of the mental healthcare ecosystem, patient journeys, and provider needs.

• Leadership & Mentorship: For Staff designers, opportunities to shape design practices, mentor junior talent, and influence product strategy.

• Cross-functional Acumen: Enhancing skills in product management, engineering collaboration, and user research methodologies.

• Professional Growth: Access to training, conferences, and development resources to continuously enhance skills and knowledge.

📝 Enhancement Note: The challenges are specific to the intersection of AI, healthcare, and user experience design, offering significant opportunities for professional growth and problem-solving.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you used AI tools to significantly accelerate your design process or improve an outcome. What was your prompt, and what was the result?"

• "How would you approach designing an AI-driven conversational flow for a patient seeking their first mental health provider, considering factors like anxiety, insurance, and provider availability?"

• "Walk me through a complex, state-heavy patient experience you designed. How did you ensure coherence and usability across different touchpoints and user states?"

• "How do you balance rapid experimentation with maintaining a cohesive and high-quality user experience, especially when leveraging AI-generated components?" Company & Culture Questions:

• "What excites you about Headway's mission, and how does your design philosophy align with making mental healthcare accessible?"

• "How do you foster collaboration with product managers and engineers, particularly in an AI-native environment where prototyping might involve code?"

• "Describe your experience contributing to or advocating for a design system like Helix. How do you ensure adoption and consistency?"

• "For Staff candidates: How have you mentored other designers, and how do you approach raising the overall craft bar of a design team?" Portfolio Presentation Strategy:

• Narrative Arc: Structure your case studies with a clear problem, your approach, your specific contributions (especially AI usage), the solution, and the measurable impact.

• Show, Don't Just Tell: Use visuals, prototypes, and data to illustrate your points effectively.

• Focus on AI: Be prepared to deeply discuss your AI prototyping process, including specific tools, prompts, iterations, and the benefits it provided.

• Quantify Impact: Clearly present the metrics that demonstrate the success of your designs. For older projects, estimate impact based on relevant industry benchmarks if direct data isn't available.

• Highlight Systems Thinking: For complex projects, explain how you considered the broader system and long-term implications.

• Prepare for Staff-Level Questions: Have examples ready for leadership, mentorship, and strategic influence.

📝 Enhancement Note: The interview preparation advice is tailored to the unique aspects of the role, particularly the AI-native requirements and the healthcare context. Candidates should be ready to articulate their AI workflow and demonstrate measurable impact.

📌 Application Steps

To apply for this operations position:

• Submit your application through the official Headway careers page via the provided job link.

• Portfolio Customization: Curate your portfolio to prominently feature 1-2 case studies that best demonstrate your experience with AI-native design, complex patient journeys, and measurable impact. Ensure AI tool usage is clearly articulated.

• Resume Optimization: Tailor your resume to highlight keywords such as "Product Design," "AI Prototyping," "Systems Thinking," "Healthcare," "Patient Experience," and any relevant AI tools (Claude Code, Cursor). Quantify achievements with metrics.

• Interview Preparation: Practice presenting your portfolio, focusing on your AI workflow, problem-solving process, and the business/user outcomes of your work. Prepare answers to strategy and behavioral questions.

• Company Research: Thoroughly research Headway's mission, values, and recent news. Understand their approach to fixing mental healthcare access and their commitment to AI. Prepare thoughtful questions for the interviewers.

⚠️ 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.