Senior Product Designer, New Channels

📍 Job Overview

Job Title: Senior Product Designer, New Channels

Company: Headway

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

Job Type: Full-Time

Category: Product Design / User Experience (UX)

Date Posted: 2026-06-05

Experience Level: Senior Level

Remote Status: Hybrid

🚀 Role Summary

• Drive the end-to-end patient experience design for Headway's crucial partnership channels, including Health Systems, Employee Assistance Programs (EAP), and Payer Partnerships.

• Develop and scale innovative patient journeys and referral-to-booking flows that ensure a seamless, trustworthy, and human-centered handoff from third-party sources into care.

• Own product strategy for new channel initiatives, leveraging data-driven experimentation and AI-native design tools to optimize conversion rates and patient retention.

• Collaborate closely with Product Management, Engineering, Sales, and Operations teams to translate partner needs and business objectives into impactful design solutions.

• Act as the primary design voice in partner meetings, using prototypes to influence multi-million-dollar relationships and shape the future of Headway's patient acquisition strategies.

📝 Enhancement Note: This role is situated within the "Patient Team" and specifically focuses on "New Channels," indicating a strategic growth area for Headway. The emphasis on B2B2C and platform constraints, alongside AI-native design workflows, suggests a forward-thinking and highly integrated design process. The responsibility to "shape what gets built" highlights a significant level of product ownership and strategic influence for the designer.

📈 Primary Responsibilities

• Design and iterate on the patient experience for Health System partnerships, encompassing the Booking Assistant (BA) tool, referrer-facing dashboards, and intake flows.

• Lead the redesign of patient onboarding and access experiences for EAP benefits, focusing on improving the utilization of free EAP sessions and exploring new product opportunities.

• Create co-branded patient journeys and landing pages for Payer Partnerships, enhancing provider directory discoverability and optimizing conversion funnels.

• Develop and execute sustained, multi-sprint experimentation plans to close the conversion gap between partnership-sourced and organically acquired patients.

• Translate complex partner requirements and user needs into intuitive and scalable design solutions, presenting prototypes and design rationale to internal teams and external partners.

• Champion an AI-native design workflow, utilizing tools like Claude, Cursor, and MagicPatterns for rapid prototyping, code generation, and iterative development throughout the product lifecycle.

• Conduct user research and analysis to identify pain points and opportunities within the partnership channels, informing design decisions and product strategy.

• Collaborate with cross-functional teams, including Payer Relations, Health System Business Development, and Operations, to ensure design solutions align with business goals and operational feasibility.

• Contribute to the development of design systems and best practices, particularly those relevant to AI-assisted design and B2B2C platform experiences.

📝 Enhancement Note: The primary responsibilities clearly delineate ownership across three key partnership channels (Health Systems, EAP, Payer). The emphasis on "scaling proven ones across new partners and segments" and "experimentation to close the conversion gap" points to a growth-focused role where data analysis and iterative design are paramount. The expectation to use AI tools for prototyping and code generation indicates a need for a designer comfortable with bleeding-edge technology.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent practical experience in product design and UX is expected.

Experience: Proven experience as a Product Designer or UX Designer, with a significant portion focused on B2B2C or platform-constrained consumer experiences. Demonstrated success in designing and scaling user-facing products within complex partnership ecosystems.

Required Skills:

• Product Strategy Instinct: Ability to proactively shape product direction based on user insights and business objectives, rather than solely executing on defined requirements.

• B2B2C Design Expertise: Experience designing consumer-facing experiences within a B2B2C framework, understanding how to create seamless and trustworthy third-party handoffs.

• Experimentation Fluency: Proven ability to design, run, and analyze multi-sprint experiments focused on conversion and retention metrics, with a mindset of learning from both positive and negative results.

• AI-Native Design Workflow: Proficiency and enthusiasm for working within an AI-native design environment, including experience with tools like Claude, Cursor, and MagicPatterns for prototyping and code generation.

• Prototyping & Iteration: Strong skills in creating interactive prototypes as primary artifacts for design validation and stakeholder communication.

• User Experience (UX) Design: Deep understanding of UX principles, user-centered design methodologies, and creating intuitive user flows.

• Conversion Optimization: Experience designing for and improving conversion rates across various user journeys and platforms.

• Stakeholder Communication: Excellent ability to communicate design decisions clearly and persuasively to non-design stakeholders, including business development, operations, and partner teams.

• Problem Framing: Comfort and skill in tackling ambiguous problems, defining the core issues, and identifying opportunities for design intervention.

Preferred Skills:

• Experience in the healthcare or mental healthcare industry.

• Familiarity with data analysis tools and methodologies for evaluating design performance.

• Understanding of front-end development principles to facilitate collaboration with engineering and work with AI-generated code.

• Experience with user research methodologies and synthesizing qualitative and quantitative data.

• Visual design and interaction design craft.

📝 Enhancement Note: The emphasis on "product strategy instinct" and thriving in "ambiguity" suggests that candidates should highlight instances where they've identified opportunities and driven product initiatives, not just executed them. The AI-native requirement is critical; candidates should be prepared to discuss their current or desired workflow with these tools. Experience with experimentation is also a key differentiator, requiring candidates to quantify the impact of their A/B tests.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least one significant B2B2C or platform-constrained consumer experience project, detailing the challenges of third-party handoffs and how they were addressed.

• Include case studies demonstrating a strong understanding of product strategy, including how user insights and business goals informed design decisions.

• Present a project where experimentation played a key role in iterating on design solutions and driving measurable improvements in conversion or retention.

• Highlight examples of using AI tools (e.g., Claude, Cursor, MagicPatterns) in the design process, showcasing how these technologies were leveraged for prototyping, iteration, or code generation.

• Demonstrate the ability to communicate complex design decisions and rationale to non-technical and non-design stakeholders, potentially through presentation examples or descriptions of partner interactions. Process Documentation:

• Detail the process of defining problems and framing opportunities within ambiguous contexts, illustrating how you moved from uncertainty to actionable design solutions.

• Explain your approach to running and analyzing multi-sprint experiments, including how you set up tests, tracked metrics, and incorporated learnings into subsequent design iterations.

• Describe your workflow for collaborating with cross-functional teams (Product, Engineering, BD, Ops) on design projects, emphasizing communication and alignment strategies.

• Provide examples of how you've used prototypes as persuasive tools in partner meetings or for influencing key stakeholders.

📝 Enhancement Note: The portfolio should not just be a collection of visually appealing designs. It needs to tell a story about strategic thinking, problem-solving, and measurable impact, with a specific focus on partnership dynamics and the emerging use of AI in design. Candidates should be prepared to walk through their portfolio, explaining their thought process and the business outcomes of their work.

💵 Compensation & Benefits

Salary Range: The expected base pay range for this position is $180,000 - $225,000 USD per year. This range is determined by factors such as qualifications, experience, and geographic location.

Benefits:

• Equity Compensation: Meaningful ownership opportunities through stock options or grants.

• Health & Wellness: Comprehensive Medical, Dental, and Vision coverage.

• Financial Well-being: Health Savings Account (HSA) / Flexible Spending Account (FSA), 401K retirement savings plan.

• Work-Life Support: Work-from-Home Stipend, Therapy Reimbursement, Employee Assistance Program (EAP).

• Family Support: 16-week parental leave for eligible employees, Carrot Fertility annual reimbursement and membership.

• Time Off: 13 paid holidays annually, a dedicated Holiday Break between December 25th and December 31st, and Flexible Paid Time Off (PTO).

• Professional Development: Access to training and professional development opportunities.

Working Hours: The standard working hours are typically 40 hours per week, aligning with full-time employment expectations. The hybrid work arrangement suggests flexibility in structuring these hours, with potential for remote work days and in-office collaboration.

📝 Enhancement Note: The salary range is competitive for a Senior Product Designer role in major tech hubs like New York, San Francisco, and Seattle. The comprehensive benefits package, particularly the emphasis on mental health support (Therapy Reimbursement, EAP), aligns with Headway's mission. The inclusion of a Work-from-Home Stipend and flexible PTO further supports a modern, hybrid work environment.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology (specifically focused on mental healthcare access and insurance). Headway operates at the intersection of healthcare, technology, and finance, aiming to disrupt traditional mental healthcare access by leveraging technology to solve insurance and administrative barriers.

Company Size: Headway is a Series D funded company with over 75,000 providers on its platform, indicating a significant and rapidly scaling organization. This size suggests a dynamic environment with established processes but also ample room for innovation and individual impact.

Founded: Headway was founded with the mission to fix the inaccessibility of mental healthcare due to cost and insurance complexities. This foundational purpose drives its company culture and product development.

Team Structure:

• Patient Team: The role is part of the Patient team, responsible for the patient's journey and acquisition.

• Design Team: The designer will be the sole designer for the "New Channels" vertical within the Patient Team and will report to the Director of Product Design for Patient. This implies a high degree of autonomy and ownership.

• Cross-Functional Collaboration: Close partnerships are expected with a Staff PM, engineering teams, Payer Relations, Health System BD, and Operations.

Methodology:

• AI-First Design: Headway is committed to an AI-first design approach, integrating AI tools like Claude, Cursor, and MagicPatterns into the daily workflow for prototyping, coding, and iteration.

• Experimentation-Driven: A strong emphasis on running sustained experiments to measure impact and drive product improvements, particularly for conversion rate optimization.

• Data-Informed Decision Making: Design decisions are expected to be informed by user insights, conversion metrics, and A/B testing results.

Company Website: https://headway.co/

📝 Enhancement Note: The company's mission to make mental healthcare accessible is a strong cultural anchor. The AI-first design team is a significant differentiator, indicating a commitment to leveraging cutting-edge technology for efficiency and innovation. The "New Channels" focus suggests a growth-oriented and entrepreneurial spirit within a well-funded, established company.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, indicating a position of significant individual contribution and strategic influence. The designer is expected to own specific product areas, shape strategy, and act as a key decision-maker within their domain.

Reporting Structure: The Senior Product Designer will report to the Director of Product Design for Patient. This provides a clear reporting line while allowing for substantial autonomy in day-to-day work and project execution. The role is the sole designer for the "New Channels" vertical within the Patient Team, emphasizing direct impact and ownership.

Operations Impact: The work of this role directly impacts Headway's growth by optimizing patient acquisition through key partnerships. Success means driving millions of dollars in revenue through improved conversion rates and successful partner integrations, directly contributing to the company's mission of expanding access to mental healthcare.

Growth Opportunities:

• Product Leadership: Potential to grow into a lead designer role for a specific vertical or team, mentoring other designers and shaping broader design strategy.

• AI Design Specialization: Deepen expertise in AI-native design workflows, becoming a leader in this emerging field within the company.

• Cross-Functional Expertise: Develop a strong understanding of business development, operations, and payer relations through close collaboration, opening doors to roles with broader strategic scope.

• Impactful Product Development: Contribute to the evolution of a critical platform in the mental healthcare space, gaining experience in scaling a mission-driven technology company.

📝 Enhancement Note: The "Senior" title combined with "owning" specific channels and being the "only designer in the room" suggests a role with significant responsibility and potential for rapid advancement. The AI-native aspect offers a unique opportunity for skill development in a rapidly evolving design landscape.

🌐 Work Environment

Office Type: Headway offers a hybrid work model, allowing for a mix of remote and in-office work. This suggests a flexible environment that balances focused individual work with collaborative team interactions.

Office Location(s): The role is available in New York, NY; San Francisco, CA; and Seattle, WA. These are major tech hubs, implying access to vibrant professional communities and well-equipped office spaces.

Workspace Context:

• Collaborative Environment: The hybrid model necessitates intentional collaboration. Designers will work closely with product managers, engineers, and business teams, often requiring structured meetings, design critiques, and shared digital workspaces.

• AI Tools Integration: The workspace is equipped with AI tools (Claude, Cursor, MagicPatterns), indicating a tech-forward environment where designers are expected to leverage these tools for efficiency and innovation.

• Cross-Functional Interaction: Opportunities for regular interaction with diverse teams, including business development, operations, and partner management, fostering a holistic understanding of the business.

Work Schedule: The standard work schedule is typically 40 hours per week, consistent with full-time employment. The hybrid arrangement offers flexibility in how these hours are structured, allowing for in-office days for collaboration and remote days for focused work.

📝 Enhancement Note: The hybrid nature of the role means candidates should be comfortable with both remote autonomy and in-office collaboration. The choice of locations (NYC, SF, SEA) suggests access to well-resourced offices and a vibrant talent pool. The integration of AI tools into the daily workflow is a key characteristic of the work environment.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application, resume, and portfolio to assess qualifications and alignment with the role.

• Design/Product Challenge: Likely an exercise to assess product strategy, problem-solving, and design skills, potentially involving AI tool usage or a case study presentation. This may be a take-home assignment or a live session.

• Portfolio Presentation: A deep dive into your portfolio, where you'll present 1-2 key projects, explaining your process, strategic thinking, and outcomes, with a focus on B2B2C, experimentation, and AI integration.

• Team & Stakeholder Interviews: Meetings with the Director of Product Design, Staff PM, Engineering leads, and potentially members of BD or Ops teams to evaluate collaboration style, communication skills, and cultural fit.

• Final Round: Interviews with senior leadership to discuss strategic alignment and overall fit for Headway.

Portfolio Review Tips:

• Showcase Strategic Thinking: Prioritize projects where you influenced "what to build" based on user insights and business goals, not just "how it looks."

• Highlight B2B2C Nuances: Clearly articulate the unique challenges of designing for third-party handoffs and your solutions for creating seamless, trustworthy experiences.

• Demonstrate Experimentation Impact: Quantify the results of your A/B tests and experiments, emphasizing your learnings and iterative process.

• Integrate AI Workflow: Explicitly show how you've used AI tools (Claude, Cursor, MagicPatterns) in your process, detailing the benefits and outcomes.

• Storytelling: Structure your case studies with a clear narrative: problem, your role, process, solution, and measurable results. Use visuals effectively to support your story.

• Partner Communication: Be prepared to discuss how you communicate design decisions to non-design stakeholders, using prototypes as persuasion tools.

Challenge Preparation:

• Anticipate AI Integration: Expect design challenges that encourage or require the use of AI tools. Be ready to demonstrate your proficiency and innovative use of these technologies.

• Focus on Metrics: Prepare to discuss how you measure success and optimize for conversion and retention. Have specific examples of metrics you've influenced.

• Problem Framing: Practice articulating how you approach ambiguous problems and define the scope of a design challenge.

• Cross-Functional Scenarios: Be ready to discuss how you would collaborate with PM, Engineering, BD, and Ops on a given problem, considering their perspectives.

📝 Enhancement Note: The interview process emphasizes a blend of design craft, strategic thinking, and technical proficiency, particularly with AI tools. Candidates should be prepared to demonstrate not only their design skills but also their ability to drive product strategy and collaborate effectively in a fast-paced, AI-native environment.

🛠 Tools & Technology Stack

Primary Tools:

• AI Design Tools: Claude, Cursor, MagicPatterns (central to Headway's design workflow for prototyping, code generation, and iteration).

• Prototyping Tools: Figma (or similar industry-standard tools for wireframing, high-fidelity mockups, and interactive prototyping).

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

Analytics & Reporting:

• Experimentation Platforms: Tools for running A/B tests and analyzing conversion data (specific tools not listed, but proficiency in data-driven iteration is key).

• Analytics Platforms: Familiarity with web and product analytics tools (e.g., Amplitude, Google Analytics) for understanding user behavior and tracking key metrics.

CRM & Automation:

• CRM: While not directly a CRM role, understanding how patient acquisition funnels integrate with CRM systems or partner platforms may be beneficial.

• Collaboration Tools: Slack, Notion, or similar for team communication and documentation.

• Project Management Tools: Tools like Jira or Asana for tracking design tasks and project progress.

📝 Enhancement Note: Proficiency with AI design tools is a non-negotiable requirement for this role. Candidates should be prepared to discuss their experience and comfort level with Claude, Cursor, and MagicPatterns. Familiarity with standard design and prototyping tools like Figma is also expected, alongside an understanding of how design integrates with analytics and experimentation platforms.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to Headway's mission of making mental healthcare accessible. This value influences decision-making and prioritizes impact.

• AI-Native Innovation: Embracing and actively utilizing AI tools to enhance design processes, speed up iteration, and explore new creative possibilities.

• Data-Driven Experimentation: A culture that values hypothesis testing, A/B testing, and data analysis to validate design decisions and drive measurable improvements.

• Collaboration & Transparency: Open communication and a willingness to share work, provide feedback, and work closely with cross-functional teams.

• User-Centricity: A deep focus on understanding and serving the needs of patients, even within complex B2B2C partnerships.

Collaboration Style:

• Cross-Functional Integration: Designers are expected to work seamlessly with Product Managers, Engineers, Business Development, and Operations teams, acting as a bridge between user needs and business objectives.

• Prototyping as a Communication Tool: Prototypes are used extensively to align stakeholders, gather feedback, and drive consensus, especially in partner discussions.

• Feedback-Rich Environment: A culture that encourages constructive feedback on designs and processes to foster continuous improvement and learning.

• Agile and Iterative: The team likely operates with agile methodologies, embracing iterative development cycles and adapting to new insights and requirements.

📝 Enhancement Note: The core values revolve around mission, innovation (especially AI), data, collaboration, and user focus. Candidates should be able to articulate how they embody these values in their work, particularly how they leverage AI and data in their design process and collaborate with diverse teams.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating B2B2C Complexity: Designing for multiple stakeholders (patient, partner organization, internal teams) and ensuring a seamless experience across disparate systems and branding.

• Balancing Partnership Needs with User Experience: Reconciling the specific requirements and branding of health systems, EAPs, and payers with Headway's core user experience goals.

• Driving Conversion in Partnership Channels: Closing the gap between partnership-sourced patient acquisition and organic acquisition, requiring sophisticated experimentation and optimization strategies.

• Adopting and Leading with AI Tools: Continuously learning and integrating new AI capabilities into the design workflow, potentially leading to challenges in tool adoption and workflow optimization.

• Ambiguity in New Channels: Defining and building out new product experiences for emerging partnership channels, requiring strong strategic thinking and initiative.

Learning & Development Opportunities:

• AI Design Mastery: Becoming a highly skilled practitioner in AI-native design workflows, a critical and evolving area in the tech industry.

• Product Strategy Development: Gaining in-depth experience in shaping product roadmaps and influencing business strategy through design leadership.

• Healthcare Industry Expertise: Deepening knowledge of the healthcare ecosystem, its complexities, and how technology can drive access and improvement.

• Cross-Functional Acumen: Developing a comprehensive understanding of sales, partnerships, operations, and engineering functions within a scaling tech company.

• Leadership Potential: Opportunities to grow into lead design roles, mentor junior designers, and contribute to the evolution of Headway's design practice.

📝 Enhancement Note: The challenges highlight the strategic importance and complexity of the role, particularly the blend of B2B2C, AI, and healthcare. The growth opportunities are significant, offering a chance to become a leader in both product design and cutting-edge AI technologies within a mission-driven organization.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design a consumer experience within B2B2C or platform constraints. What were the key challenges, and how did you ensure the experience felt native and trustworthy?" (Focus on third-party handoff, stakeholder management, and user experience.)

• "Walk us through an experiment you designed and ran that significantly impacted conversion or retention metrics. What was your hypothesis, methodology, results, and key learnings?" (Emphasize data-driven design, experimentation process, and quantifiable outcomes.)

• "How do you approach a product challenge where the problem space is ambiguous? Describe a situation where you had to 'figure out what to build' and how you navigated that uncertainty." (Highlight problem framing, user research, and strategic initiative.) Company & Culture Questions:

• "What interests you about Headway's mission to improve mental healthcare access, and how does that align with your personal values?" (Show genuine interest and mission alignment.)

• "How do you see AI tools like Claude, Cursor, and MagicPatterns fitting into a product design workflow? How have you used them, or how would you integrate them into your process here?" (Demonstrate enthusiasm and practical application of AI in design.)

• "Describe your experience working in a hybrid or remote environment, and how you maintain strong collaboration with remote and in-office colleagues." (Focus on communication and collaboration strategies.) Portfolio Presentation Strategy:

• Select Projects Wisely: Choose 1-2 projects that best showcase your B2B2C experience, strategic product thinking, and experimentation skills. Ensure at least one highlights your use of AI tools.

• Structure Your Narrative: For each project, clearly articulate the problem, your specific role and contributions, the strategic decisions you made, your design process (including AI integration), the solutions, and the measurable impact.

• Quantify Results: Whenever possible, use data and metrics to demonstrate the success of your designs, especially regarding conversion rates and user engagement.

• Explain AI Integration: Be prepared to detail how you used AI tools. Did they help with ideation, prototyping, code generation, or something else? What was the benefit?

• Anticipate Questions: Prepare for questions about your design rationale, trade-offs you made, how you handled feedback, and how your work aligns with Headway's mission and values.

📝 Enhancement Note: Interview preparation should strongly emphasize the AI-native aspect of the role. Candidates should be ready to discuss their experiences and ideas regarding AI in design. Demonstrating strategic thinking beyond just visual execution is crucial, as is quantifying the impact of their work through metrics and experimentation.

📌 Application Steps

To apply for this Senior Product Designer position:

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

• Curate Your Portfolio: Select 1-2 key projects that best demonstrate your expertise in B2B2C design, product strategy, and experimentation. Ensure you explicitly showcase your use of AI tools like Claude, Cursor, or MagicPatterns in your process and highlight the measurable impact of your work.

• Optimize Your Resume: Tailor your resume to highlight experience in product design, UX, B2B2C platforms, AI-native workflows, and experimental design. Use keywords from the job description to ensure ATS compatibility and draw attention to quantitative achievements.

• Prepare Your Presentation: Practice walking through your chosen portfolio projects, focusing on clear storytelling, strategic rationale, and quantifiable results. Be ready to discuss your AI design process and how you approach ambiguous problems.

• Research Headway: Familiarize yourself with Headway's mission, product, and recent news. Understand their approach to mental healthcare access and their commitment to an AI-first design philosophy.

⚠️ 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.