Senior Product Designer, New Channels

📍 Job Overview

Job Title: Senior Product Designer, New Channels

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 / User Experience (UX)

Date Posted: 2026-06-05T14:45:48

Experience Level: Mid-Senior Level

Remote Status: Hybrid

🚀 Role Summary

• Design and scale patient experiences for Headway's partnership channels, including Health Systems, Employee Assistance Programs (EAP), and Payer Partnerships, focusing on seamless third-party handoffs into care.

• Drive product strategy and execution for new channel initiatives, leveraging AI tools for rapid prototyping and iteration within an AI-native design environment.

• Own the end-to-end design process, from initial problem discovery and ideation to experimentation, iteration, and launch, with a strong emphasis on conversion and retention metrics.

• Collaborate closely with Product Management, Engineering, and cross-functional teams (Payer Relations, Health System BD, Ops) to define and deliver innovative solutions that improve patient access to mental healthcare.

• Act as the sole designer for these critical channels, influencing multi-million dollar partner relationships through compelling prototypes and persuasive design presentations.

📝 Enhancement Note: This role is positioned as a Senior Product Designer with a specific focus on "New Channels," indicating a strategic growth area for Headway. The emphasis on B2B2C, platform constraints, and third-party handoffs suggests a need for designers experienced in complex ecosystems where user experience bridges multiple entities (patient, partner, Headway). The AI-native aspect is a significant differentiator, requiring candidates comfortable with cutting-edge design workflows.

📈 Primary Responsibilities

• Health Systems Channel Design: Lead the design of the referral-to-booking experience for patients referred through health system partners, including the Booking Assistant (BA) tool, referrer-facing dashboards, and new intake flows.

• EAP Channel Design: Develop and redesign user journeys for patients accessing mental healthcare via employer EAP benefits, focusing on onboarding, maximizing free session utilization, and exploring new product opportunities within this channel.

• Payer Partnerships Design: Create co-branded patient journeys, enhance provider directory discoverability, and optimize conversion funnels for patients sourced through payer channels.

• Experimentation & Optimization: Design, implement, and analyze multi-sprint experiments to close the conversion gap between partnership-sourced and organically acquired patients, using data to drive design decisions and product improvements.

• AI-Native Design Workflow: Integrate AI tools (Claude, Cursor, MagicPatterns) into the daily design process for problem clarification, assumption testing, rapid prototyping, and iterating on design solutions directly with code.

• Cross-functional Collaboration: Partner closely with Product Managers, Engineers, Payer Relations, Health System Business Development, and Operations teams to ensure alignment and successful execution of design initiatives.

• Stakeholder Communication: Present design concepts, prototypes, and findings to internal teams and external partners (including BD and Ops) to influence strategy and secure buy-in.

📝 Enhancement Note: The responsibilities clearly delineate ownership across three key partnership channels, emphasizing a need for a designer who can manage multiple distinct but interconnected user experiences. The explicit mention of "AI-First design team" and specific tools (Claude, Cursor, MagicPatterns) indicates a requirement for candidates with demonstrable experience or strong aptitude in leveraging AI for design productivity and innovation.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's or Master's degree in Design, HCI, Computer Science, or a related field is typically expected for a Senior Product Designer role. Equivalent practical experience will also be considered.

Experience: Minimum of 5-7 years of experience in Product Design or UX Design, with a significant portion focused on consumer-facing experiences within B2B2C or platform environments.

Required Skills:

• Proven experience designing consumer experiences within B2B2C or complex platform constraints, with a strong understanding of third-party handoffs and building trust.

• Demonstrated product strategy instinct; ability to proactively shape product direction based on customer insights and business objectives, not just execute design tasks.

• Fluency in experimentation methodologies, including designing, running, and analyzing multi-sprint A/B tests with a focus on conversion and retention metrics.

• Strong proficiency in rapid prototyping tools, with a specific emphasis on AI-powered design tools such as Claude, Cursor, and MagicPatterns.

• Excellent communication and presentation skills, with the ability to articulate design decisions and influence non-design stakeholders (e.g., BD, Ops, partners).

• Experience translating ambiguous problem spaces into clear product requirements and actionable design solutions.

• User-centered design approach with a strong understanding of user research, journey mapping, and usability testing principles. Preferred Skills:

• Experience in the healthcare or mental health technology sector.

• Familiarity with data analysis and working with analytics platforms to inform design decisions.

• Experience designing for referral systems, provider directories, or patient intake workflows.

• Ability to work effectively in a fast-paced, startup environment with evolving priorities.

• Understanding of front-end development principles to facilitate effective collaboration with engineers.

📝 Enhancement Note: The requirements emphasize a blend of strategic thinking, hands-on design craft, and a forward-thinking approach to technology adoption (AI). The "only designer in the room" aspect for these channels suggests a need for a highly autonomous and proactive individual.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• B2B2C Case Studies: Showcase at least 2-3 detailed case studies demonstrating experience designing consumer-facing products within a B2B2C context or complex platform. Highlight how you managed third-party integrations or partner requirements.

• Product Strategy & Problem Solving: Include examples where you identified a user problem or business opportunity and proactively defined the solution, outlining your strategic thinking process.

• Experimentation & Iteration: Present case studies that detail your involvement in designing and running experiments, including hypothesis formulation, A/B test design, analysis of results, and subsequent iterations based on learnings.

• AI-Powered Design Process: If possible, include examples or describe your approach to using AI tools in your design workflow, demonstrating how they enhanced your productivity or the quality of your output.

• Conversion Optimization: Showcase projects where you directly impacted conversion rates, user engagement, or retention metrics, clearly articulating the problem, your solution, and the quantifiable results.

Process Documentation:

• Problem Definition & Research: Detail how you approach understanding a new problem space, including user research methodologies, competitive analysis, and stakeholder interviews.

• Design Process Walkthrough: Illustrate your end-to-end design process from ideation and wireframing to high-fidelity prototyping and user testing, emphasizing iterative refinement.

• Collaboration & Communication: Provide examples of how you documented and communicated design decisions, requirements, and findings to cross-functional teams and external partners.

• Metrics & Impact: Demonstrate how you define, track, and report on the success of your designs using key performance indicators (KPIs) and business metrics.

📝 Enhancement Note: For a senior role, especially one with significant ownership and strategic input, the portfolio needs to go beyond visual design. It should clearly articulate the candidate's strategic thinking, problem-solving abilities, and impact on business outcomes, particularly through experimentation and AI-driven workflows.

💵 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

• 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, 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: The standard working hours are typically around 40 hours per week, common for full-time roles. Flexibility may be offered, but the demands of the role, especially with cross-functional collaboration and potential partner interactions, suggest a need for consistent availability.

📝 Enhancement Note: The salary range is competitive for a Senior Product Designer in major US tech hubs. The comprehensive benefits package, including equity, robust health coverage, significant parental leave, and professional development, reflects a company committed to employee well-being and growth. The AI-native focus may also imply a need for candidates comfortable with a modern, potentially more flexible, work approach.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology / Mental Healthcare Access

Company Size: Headway is a Series D funded company with over 75,000 providers on its platform, indicating a significant and rapidly growing organization. While the exact employee count isn't provided, Series D funding and broad provider adoption suggest a company size likely in the hundreds of employees, with a substantial engineering and product team.

Founded: Headway was founded to address the accessibility gap in mental healthcare, aiming to build a new system where care is affordable and accessible via insurance.

Team Structure:

• Patient Team: This role is within the "Patient team," suggesting a focus on the end-user experience for individuals seeking care.

• AI-First Design Team: Designers are part of an "AI-first" initiative, integrating AI tools deeply into their workflow.

• Reporting: The role reports to the Director of Product Design for Patient.

• Collaboration: Close partnerships are expected with Staff PM, Engineering, Payer Relations, Health System BD, and Operations teams.

Methodology:

• AI-Driven Design: The team leverages AI tools (Claude, Cursor, MagicPatterns) extensively for problem definition, prototyping, and iteration.

• Experimentation-Focused: A strong emphasis is placed on running sustained experiments to drive measurable improvements in conversion and retention.

• User-Centric & Partner-Centric: Design efforts are informed by both patient needs and the requirements of strategic partners (Health Systems, EAPs, Payers).

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

📝 Enhancement Note: Headway's mission-driven culture in the mental healthcare space is a significant draw. The explicit "AI-First Design Team" is a key differentiator, indicating a forward-thinking approach to design processes and a need for adaptable, tech-savvy designers.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, signifying a mid-to-senior level position. It implies a need for significant autonomy, strategic input, and the ability to mentor or guide less experienced designers. The "only designer in the room" aspect for these channels further elevates the seniority and impact of the role.

Reporting Structure: The role reports to the Director of Product Design for Patient. This structure suggests opportunities for direct mentorship from a design leader and visibility into broader patient product strategy. The close collaboration with a Staff PM and other cross-functional leads indicates a highly collaborative and matrixed environment.

Operations Impact: The work directly impacts Headway's growth through strategic partnerships. By improving the patient experience for Health Systems, EAPs, and Payers, this role contributes to patient acquisition, retention, and ultimately, the company's mission of making mental healthcare accessible. The design decisions directly influence multi-million dollar partner relationships and patient conversion rates.

Growth Opportunities:

• Specialization: Deepen expertise in B2B2C design, partnership channel optimization, and AI-driven design workflows.

• Leadership: Potential to grow into a lead role for a specific channel or product area, or to mentor junior designers as the team expands.

• Strategic Influence: Contribute significantly to the product roadmap and strategic direction for Headway's partnership channels.

• Skill Development: Continuous learning and adoption of cutting-edge AI design tools and methodologies.

• Impact: Drive meaningful change in mental healthcare accessibility, contributing to a high-impact mission.

📝 Enhancement Note: The Senior title, combined with sole ownership for key channels and the AI-native focus, presents a substantial growth opportunity for a designer looking to make a significant impact and advance their career in a rapidly evolving design landscape.

🌐 Work Environment

Office Type: Headway operates with a hybrid work model. While specific office details aren't provided, the presence of multiple office locations (New York, San Francisco, Seattle) suggests physical hubs for collaboration. The "Work-from-Home Stipend" further supports a flexible approach.

Office Location(s): The role is available in New York, NY; San Francisco, CA; and Seattle, WA. This indicates that candidates must be located in or willing to relocate to one of these major tech hubs.

Workspace Context:

• Collaborative Environment: The hybrid model and emphasis on cross-functional teams suggest a dynamic work environment that balances focused individual work with collaborative sessions.

• AI-Enabled Tools: Designers will have access to and be expected to utilize advanced AI tools integrated into their workflow, potentially enhancing productivity and creative output.

• Cross-functional Interaction: Frequent interaction with Product, Engineering, Business Development, and Operations teams is expected, fostering a holistic product development culture.

Work Schedule: A standard 40-hour work week is typical, but the fast-paced nature of a Series D startup and the need to collaborate with various teams and potentially partners across different time zones may require flexibility. The emphasis on experimentation and iteration suggests a focus on outcomes and impact rather than strict adherence to hours.

📝 Enhancement Note: The hybrid model combined with AI integration points to a modern, results-oriented work environment. Candidates should be comfortable with a mix of remote and in-office collaboration, and eager to embrace new technological paradigms in their daily work.

📄 Application & Portfolio Review Process

Interview Process:

1. Initial Screening: A recruiter will assess your background, experience, and alignment with the role, particularly your interest in Headway's mission and your experience with B2B2C and AI design.

2. Hiring Manager Interview: A conversation with the Director of Product Design for Patient to discuss your experience, design philosophy, and approach to product strategy and experimentation.

3. Portfolio Presentation & Design Exercise: A session where you present your portfolio, highlighting relevant case studies. This may include a take-home design challenge or an in-person/virtual design exercise focused on a problem relevant to the role's responsibilities (e.g., optimizing a referral flow).

4. Cross-functional Team Interviews: Meetings with key collaborators, including Product Managers, Engineers, and potentially members of BD or Ops, to assess your collaboration skills, technical understanding, and cultural fit.

5. Final Interview: A concluding discussion, potentially with senior leadership, to confirm fit and discuss final details.

Portfolio Review Tips:

• Focus on Impact: Structure your case studies around the problem, your strategic approach, your design solutions, and most importantly, the measurable impact and outcomes (conversion metrics, user engagement, partner satisfaction).

• Showcase B2B2C Nuances: Clearly explain the complexities of designing for users within a partner's ecosystem and how you navigated those constraints.

• Highlight AI Integration: If you have examples, describe how you used AI tools to accelerate your process, iterate faster, or achieve better results. Be prepared to discuss your philosophy on AI in design.

• Demonstrate Strategy: Go beyond "making it look good." Articulate why you made certain design decisions, linking them back to user needs, business goals, and experimentation hypotheses.

• AI-Native Readiness: Be prepared to discuss your enthusiasm and readiness for an AI-native design environment. If you have prior experience, this is your chance to shine.

Challenge Preparation:

• Understand the Channels: Research Headway's existing partnership channels (Health Systems, EAP, Payers) and the typical user journeys involved.

• Embrace Ambiguity: The role thrives on "figuring out what to build." Be ready to tackle open-ended problems and demonstrate your ability to structure your thinking.

• AI Tool Familiarity: Familiarize yourself with the mentioned AI tools (Claude, Cursor, MagicPatterns) or similar technologies, and be ready to discuss how you would leverage them for the challenge.

• Metrics-Driven Approach: Prepare to discuss how you would measure success for any proposed solution, focusing on conversion, retention, and user satisfaction.

📝 Enhancement Note: The emphasis on AI tools and the "only designer" aspect means candidates need to showcase not just design craft but also strategic autonomy, problem-solving skills, and a proactive, experimental mindset. The portfolio should reflect this.

🛠 Tools & Technology Stack

Primary Tools:

• AI Design Suite: Claude (for problem clarification, assumption testing, content generation), Cursor (AI-integrated code editor for design iteration), MagicPatterns (AI-powered UI pattern generation and prototyping). Candidates are expected to be proficient or quickly learn these.

• Prototyping Tools: While AI tools are primary, proficiency in standard prototyping tools like Figma, Sketch, or Adobe XD may still be beneficial for certain workflows or for demonstrating core design principles.

• Design Software: Standard design tools for creating detailed UI assets and flows.

Analytics & Reporting:

• Analytics Platforms: Experience with tools like Google Analytics, Amplitude, Mixpanel, or similar platforms to track user behavior, experiment results, and conversion metrics.

• Data Visualization: Ability to interpret and present data, potentially using tools like Tableau, Looker, or internal dashboards.

CRM & Automation:

• CRM: Familiarity with CRM systems (e.g., Salesforce, HubSpot) would be beneficial for understanding how patient acquisition and partner management tie into the broader business operations.

• Workflow Tools: Experience with project management and collaboration tools like Jira, Asana, or Trello for managing design tasks and sprint cycles.

• Integration Concepts: Understanding of how different systems (CRM, patient platforms, partner portals) might integrate to create seamless user journeys.

📝 Enhancement Note: The explicit mention of AI tools is critical. Candidates need to demonstrate not just familiarity but a proactive approach to integrating these tools into their design process. This is a key differentiator for Headway's design team.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to Headway's mission of making mental healthcare accessible and affordable. This should translate into design decisions that prioritize patient well-being and ease of access.

• AI-Native & Innovative: Embracing cutting-edge technology, particularly AI, as a core component of the design workflow to drive efficiency and creativity.

• Data-Informed & Experimental: Relying on data and rigorous experimentation to validate hypotheses and drive continuous improvement in user experience and conversion rates.

• Collaborative & Transparent: Working closely with cross-functional teams and partners, fostering open communication and shared ownership of product outcomes.

• Empathetic & User-Centric: Deep understanding and empathy for patients navigating the complexities of mental healthcare access and for partners seeking reliable solutions.

Collaboration Style:

• Cross-functional Integration: Designers are integrated into product teams, working hand-in-hand with PMs and Engineers from discovery through launch and iteration.

• Partner-Focused: A willingness to engage with and understand the needs of external partners (Health Systems, EAPs, Payers), translating those needs into actionable design solutions.

• Feedback-Rich Environment: An expectation of constructive feedback, both giving and receiving, to continuously improve designs and processes.

• Proactive Communication: Designers are expected to proactively communicate progress, challenges, and insights to relevant stakeholders.

📝 Enhancement Note: The "AI-First" and "Experimental" values are paramount. Candidates should demonstrate how they embody these principles in their work and how they approach collaboration within a fast-paced, innovative environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complex B2B2C Ecosystems: Navigating the distinct needs and constraints of patients, referral partners (health systems, EAPs), and payers simultaneously to create a cohesive experience.

• Driving Conversion in Partnership Channels: Closing the conversion gap between partnership-sourced and organic patients requires sophisticated experimentation and nuanced design solutions.

• Rapidly Evolving AI Landscape: Staying ahead of the curve in AI design tools and methodologies, and effectively integrating them into established workflows.

• Ambiguity and Prioritization: Thriving in a role where "figuring out what to build" is a core responsibility, requiring strong self-direction and prioritization skills.

• Scaling Proven Solutions: Adapting and scaling successful designs across new partners and segments while maintaining a high-quality user experience.

Learning & Development Opportunities:

• AI Design Mastery: Becoming a leader in the application of AI tools within product design, potentially shaping best practices for the industry.

• Strategic Product Development: Gaining deep experience in product strategy, experimentation, and growth loops within a high-impact mission-driven company.

• Partner Relationship Design: Developing expertise in designing for and influencing strategic B2B partnerships.

• Career Advancement: Potential to grow into a Lead Designer role, manage design initiatives, or transition into product management or design leadership.

• Industry Impact: Contributing directly to solving a critical societal problem – access to mental healthcare.

📝 Enhancement Note: The challenges are directly tied to the role's unique responsibilities, particularly the AI integration and B2B2C complexity. The growth opportunities highlight the potential for significant professional development and impact.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a consumer experience within a B2B2C context. What were the unique challenges, and how did you ensure a seamless handoff for the end-user?" (Focus on your understanding of multi-stakeholder design and user journey mapping.)

• "How would you approach designing a new intake flow for patients referred through a major health system, considering their existing systems and our need for efficient data capture?" (Demonstrate structured problem-solving, user empathy, and an understanding of partner integration.)

• "Walk me through an experiment you designed and ran to improve conversion rates. What was your hypothesis, how did you measure success, and what did you learn?" (Highlight your experimental rigor, data-driven approach, and ability to iterate.) Company & Culture Questions:

• "Why are you drawn to Headway's mission, and how do you see your role as a designer contributing to it?" (Show genuine interest in the mission and connect it to your design values.)

• "Our design team is AI-first. How have you used AI tools in your design process previously, or how do you envision using them at Headway to accelerate your work?" (Be prepared to discuss specific tools and your philosophy on AI in design; enthusiasm is key.)

• "How do you approach collaborating with Product Managers and Engineers when you're the sole designer for a specific product area?" (Emphasize communication, transparency, and partnership.) Portfolio Presentation Strategy:

• Storytelling is Key: Frame each case study as a narrative: the problem, your role and approach (strategy, research, design), the solution, and the impact (quantifiable results).

• Focus on B2B2C and AI: Select case studies that best showcase your experience with complex ecosystems and, if possible, your use of AI tools. Explicitly call out these aspects.

• Show, Don't Just Tell: Use visuals (wireframes, mockups, prototypes, data charts) to illustrate your points. Be prepared to walk through interactive prototypes.

• Quantify Impact: Whenever possible, present metrics that demonstrate the success of your designs (e.g., % increase in conversion, % decrease in drop-off, partner satisfaction scores).

• Be Ready for "What Ifs": Anticipate follow-up questions about alternative solutions, trade-offs, or how you'd handle specific challenges in the role.

📝 Enhancement Note: The interview process will likely test for strategic thinking, adaptability to AI, and the ability to operate autonomously. Candidates should prepare to articulate their process, impact, and passion for Headway's mission.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the official Headway careers page at https://headway.co/careers.

• Curate Your Portfolio: Select 2-3 of your strongest case studies that best demonstrate your B2B2C design experience, product strategy capabilities, and any experience with AI-driven design workflows or experimentation. Emphasize clear problem definition, your strategic approach, and quantifiable outcomes.

• Tailor Your Resume: Highlight keywords from the job description, such as "Product Design," "B2B2C," "AI-Native Design," "Experimentation," "Product Strategy," and specific tools mentioned. Quantify your achievements wherever possible.

• Prepare Your Narrative: Practice articulating your design process, your approach to problem-solving, and your enthusiasm for Headway's mission and innovative AI-first design approach. Be ready to discuss your portfolio in detail.

• Research Headway: Understand Headway's business model, mission, and its position in the mental healthcare market. Familiarize yourself with their product and any available information on their partnership channels.

⚠️ 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. Headway emphasizes that they only accept applications through their official careers page and will not refer you to external websites or ask for payment.