Senior Product Designer, Search Results

📍 Job Overview

Job Title: Senior Product Designer, Search Results

Company: Headway

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

Job Type: Full-Time

Category: Product Design / GTM Operations Support

Date Posted: 2026-09-17

Experience Level: 5-8 Years

Remote Status: Remote OK

🚀 Role Summary

• Design and own the patient search results experience, a critical surface for patient onboarding and conversion.

• Drive iterative improvements through continuous A/B testing and data analysis on a high-traffic patient-facing feature.

• Collaborate closely with Product Management, Engineering, and Research to deliver impactful design solutions.

• Utilize AI-first design tools and methodologies to accelerate prototyping, ideation, and shipping of features.

• Contribute to the evolution of the Headway design system, ensuring high craft standards for patient-facing interfaces.

📝 Enhancement Note: While this role is for a Product Designer, its focus on conversion-critical surfaces, A/B testing, data analysis, and direct impact on patient acquisition and experience strongly aligns with GTM Operations support functions. The role requires a deep understanding of user journeys, funnel optimization, and the ability to translate data into actionable design improvements, which are core competencies in operations.

📈 Primary Responsibilities

• Own the end-to-end design process for the patient search results page, including provider cards, match explanations, filtering, sorting, and handling sparse/empty states.

• Frame hypotheses, design variants, analyze results, and iterate on the search results experience based on live experiment outcomes.

• Collaborate with the Ranking team to understand available signals and the Profiles team to ensure consistent expression of provider styles and experiences.

• Partner with Product Managers and Engineering Managers to define and deliver shippable increments that advance the search results experience.

• Conduct user research, analyze patient hesitation points, and design solutions that cater to users who are unsure of their needs.

• Elevate the design craft and user experience of a high-traffic patient surface, contributing to and evolving the company's design system.

• Leverage AI tools (e.g., Claude Code, Cursor) for rapid prototyping, ideation, and contributing directly to the codebase.

📝 Enhancement Note: The emphasis on "sustained experiments," "conversion-critical surface," and "iterating on a shipped surface for weeks at a time" highlights a strong operational component. This role requires a mindset focused on continuous improvement, performance measurement, and data-driven decision-making, mirroring the core principles of Revenue Operations and GTM Operations. The expectation to "prototype in code" further underscores the need for operational efficiency and a hands-on approach to product development.

🎓 Skills & Qualifications

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

Experience: 5-8 years of experience designing consumer-facing products with demonstrated end-to-end ownership of live features.

Required Skills:

• Proven experience designing complex, information-heavy consumer products.

• Strong portfolio showcasing mature, shipped craft and iterative design on conversion-critical surfaces.

• Proficiency in designing and running A/B tests, with the ability to analyze results and drive iteration.

• Experience with user research methodologies and data analysis to inform design decisions.

• Expertise in evolving and contributing to design systems.

• Ability to partner effectively with Product Management and Engineering teams.

• Experience utilizing AI tools (e.g., Claude Code, Cursor) in the design and development process.

• Strong opinions on feature prioritization and the ability to articulate a point of view on what to remove to improve user experience. Preferred Skills:

• Experience with marketplace dynamics, search interfaces, or discovery surfaces.

• Background in healthcare or mental health technology.

• Familiarity with quantitative analysis and understanding of measurement limitations.

📝 Enhancement Note: The requirement for 5-8 years of experience and end-to-end ownership of a "live surface" indicates a mid-to-senior level role. The emphasis on "iterated on a conversion-critical surface over months" and "comfortable with numbers and skeptical of them" points to a need for analytical rigor and a data-informed approach, which is highly valued in operations roles focused on funnel optimization and revenue growth.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end ownership of at least one significant consumer product feature or surface that has been shipped and iterated upon.

• Demonstrate a deep understanding of information architecture and how to present dense information clearly and effectively.

• Include case studies that highlight the iterative design process, specifically detailing A/B tests, data analysis, and subsequent design improvements.

• Present examples of how you've contributed to or evolved a design system.

• Provide clear examples of collaboration with Product Managers and Engineers, illustrating your role in cross-functional teamwork.

• Showcase your experience with AI-powered design tools and how they were integrated into your workflow. Process Documentation:

• Clearly articulate your process for framing hypotheses, designing experimental variants, and analyzing results for A/B tests.

• Detail your approach to user research, from planning and execution to synthesizing findings and translating them into design actions.

• Explain your methodology for collaborating with data teams and understanding the metrics that drive product performance.

• Document your process for evolving design systems and ensuring consistency across product surfaces.

📝 Enhancement Note: The portfolio requirements are heavily focused on demonstrating a data-driven, iterative, and collaborative design process. This aligns with operations expectations for showcasing process optimization, measurable impact, and system-level thinking. The emphasis on "shipped craft," "iterated on a conversion-critical surface," and "what failed and what worked" requires a portfolio that tells a story of impact and learning, akin to an operations project portfolio.

💵 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.

• The role may also be eligible for equity grants. 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: 40 hours per week (Full-Time)

📝 Enhancement Note: The salary range of $180,000 - $225,000 for a Senior Product Designer in major tech hubs like New York, San Francisco, and Seattle is competitive and aligns with industry benchmarks for experienced professionals in these locations. The comprehensive benefits package, including equity, robust health coverage, and generous parental leave, reflects a company that invests in its employees' well-being and long-term commitment, which is attractive to operations professionals seeking stability and comprehensive support.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology (Mental Healthcare Access)

Company Size: Series D funded company ($325M+ in funding), indicating significant growth and established operations. The size suggests a dynamic environment with established processes but also room for innovation.

Founded: Headway was founded to address the significant gap in accessible mental healthcare, aiming to make therapy affordable by solving insurance barriers. This mission-driven approach likely shapes a culture focused on impact and user advocacy.

Team Structure:

• The role is within the Patient Onboarding pod, a cross-functional team.

• This pod includes a Staff Product Designer, a Product Manager (PM), an Engineering Manager (EM), and a Researcher.

• Close collaboration is expected with the team that computes provider relevance, indicating a strong interdependency between design, product, engineering, and data science. Methodology:

• AI-First Design: Designers are expected to use AI tools (Claude Code, Cursor) for prototyping, ideation, and shipping code. This suggests a forward-thinking, efficiency-driven approach to design and development.

• Experimentation: The pod runs continuous live experiments, meaning decisions are measured, and iteration is rapid (weeks, not months). This emphasizes a data-driven, agile methodology.

• Iterative Improvement: Designers are expected to "iterate on a shipped surface for weeks at a time," focusing on sustained optimization rather than one-off design handoffs.

Company Website: https://headway.co/

📝 Enhancement Note: The company's mission to fix mental healthcare access through technology creates a strong sense of purpose, which is often a key motivator for individuals in operations roles who value making a tangible impact. The AI-first and experimentation-driven methodologies suggest a culture that embraces innovation, efficiency, and data-backed decision-making, aligning well with the operational mindset.

📈 Career & Growth Analysis

Operations Career Level: Senior Product Designer. This level implies significant autonomy, ownership of complex features, and a strategic contribution to product direction. For operations professionals, this translates to a role with substantial influence on user acquisition funnels and patient experience optimization.

Reporting Structure: The role reports within the Patient Onboarding pod, working closely with a Staff Product Designer, PM, and EM. This structure fosters collaborative decision-making and direct impact on product outcomes.

Operations Impact: The Senior Product Designer's work directly influences patient acquisition and conversion rates by optimizing the search results experience. This role is critical in ensuring patients can find suitable therapists, which is a core GTM objective for Headway. The continuous experimentation model means the impact is measured and visible quickly.

Growth Opportunities:

• Design Leadership: Potential to grow into a Staff or Principal Designer role, leading larger initiatives or mentoring junior designers.

• Product Strategy: Opportunity to shape the strategic direction of patient onboarding and discovery features.

• Cross-functional Expertise: Deepen skills in product management, data analysis, and engineering through close collaboration.

• AI Tool Mastery: Become a leader in leveraging AI for product design and development.

• Specialization: Develop deep expertise in marketplace, search, or healthcare product design.

📝 Enhancement Note: This role offers significant growth potential, particularly in areas relevant to operations: data-driven decision-making, funnel optimization, and cross-functional strategic influence. The emphasis on AI tools also positions the candidate for future-forward skill development.

🌐 Work Environment

Office Type: The job posting lists multiple office locations (New York, San Francisco, Seattle) but also indicates "Remote OK" and "Work-from-Home Stipend." This suggests a hybrid or remote-first approach, offering flexibility.

Office Location(s):

• New York, NY

• San Francisco, CA

• Seattle, WA

• Remote within the United States is possible. Workspace Context:

• Collaborative Environment: The role is embedded within a cross-functional pod, emphasizing close teamwork with PM, EM, and Researchers.

• Tools & Technology: Access to AI tools like Claude Code and Cursor for design and prototyping, as well as standard design and collaboration software.

• Team Interaction: Frequent interaction with engineers, researchers, and product managers to iterate on designs and experiments.

Work Schedule: Standard full-time hours (approximately 40 hours/week) with flexible PTO, suggesting a balance between structured work and personal time, which is beneficial for sustained productivity in operations-focused roles.

📝 Enhancement Note: The flexibility offered by the remote option and work-from-home stipend is a significant draw for operations professionals who often require focused work time and may benefit from optimized home office setups. The collaborative pod structure ensures that even remote team members are highly integrated into the product development process.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a recruiter screen to assess basic qualifications and cultural fit.

• Portfolio Review: A deep dive into your portfolio, focusing on case studies demonstrating end-to-end ownership, iterative design, A/B testing, and AI tool usage. Be prepared to discuss your process, decisions, and outcomes.

• Design Challenge/Case Study: Potentially a take-home assignment or an in-depth discussion of a hypothetical problem related to search results or patient onboarding. This will assess your problem-solving skills, design thinking, and ability to articulate your rationale.

• Cross-functional Interviews: Meetings with PM, EM, Researcher, and potentially other designers to evaluate collaboration style, communication, and technical understanding.

• Hiring Manager Interview: Final discussion with the hiring manager to assess overall fit, strategic thinking, and alignment with the team's goals.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the problem, your solution, the process, and the measurable results (conversion improvements, engagement metrics).

• Show, Don't Just Tell: Use visuals, mockups, and prototypes to illustrate your design process and final outcomes.

• Highlight Iteration: Demonstrate how you used data, research, and experimentation to refine your designs over time.

• Emphasize AI Integration: Specifically call out how you used AI tools to enhance your workflow, speed up delivery, or improve design quality.

• Explain "Why": Be ready to defend your design decisions, especially concerning trade-offs and why certain elements were prioritized or removed.

• Tailor to the Role: Ensure your portfolio highlights experience with information-heavy interfaces, conversion optimization, and consumer-facing products.

Challenge Preparation:

• Understand Headway's Mission: Be familiar with their work in mental healthcare access and insurance.

• Analyze Search/Discovery Patterns: Review how other platforms handle search results, filtering, and personalized recommendations.

• Think Data-First: Consider what metrics would be most important for the search results page and how you would measure success.

• Embrace AI: Be prepared to discuss how AI could be leveraged to improve the search experience beyond current capabilities.

• Practice Articulation: Rehearse explaining complex design problems and solutions clearly and concisely.

📝 Enhancement Note: The emphasis on a "conversion-critical surface," "sustained experiments," and "iterating on a shipped surface" means interviewers will be looking for a candidate who thinks like an operations professional – focused on measurable outcomes, process efficiency, and continuous improvement. Preparing case studies that showcase this mindset will be crucial.

🛠 Tools & Technology Stack

Primary Tools:

• AI Design Tools: Claude Code, Cursor (expected proficiency and active use).

• Prototyping Tools: Figma, Sketch, Adobe XD (or similar, for static mocks and high-fidelity prototypes).

• Design System Tools: Figma libraries, Storybook, or similar for managing design components.

Analytics & Reporting:

• Experimentation Platforms: Tools for running A/B tests and analyzing results (specific tools not mentioned, but understanding the process is key).

• Data Visualization: Tools like Looker, Tableau, or internal dashboards for analyzing user behavior and experiment outcomes.

• User Analytics: Platforms like Amplitude, Mixpanel, or Google Analytics for tracking user interactions and funnels.

CRM & Automation:

• While not directly a CRM role, understanding how patient data flows and how design impacts the patient journey within the Headway platform is essential. This involves understanding the user lifecycle from discovery to care.

📝 Enhancement Note: The explicit mention of AI tools like Claude Code and Cursor signifies a modern, technologically advanced design environment. Proficiency in these, alongside standard design software, will be a key differentiator. For operations candidates, understanding how design decisions impact user funnels and conversion rates, and how these are tracked via analytics tools, is paramount.

👥 Team Culture & Values

Operations Values:

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

• Data-Informed: Decisions are heavily influenced by experimentation and quantitative analysis.

• User-Centric: Deep focus on understanding patient needs and hesitations to improve their journey.

• AI-Empowered: Embracing AI as a core tool for efficiency and innovation in design and development.

• Iterative & Agile: A culture of continuous improvement, rapid iteration, and learning from shipped products.

• Collaborative: Strong emphasis on cross-functional teamwork and peer feedback.

Collaboration Style:

• Pod-Based: Working within small, cross-functional teams (Product, Design, Engineering, Research) for focused execution.

• Peer Review: Openness to sharing work early and often, and providing constructive feedback.

• Data-Driven Debate: Discussions are grounded in data, experiment results, and user insights.

• AI as a Partner: Integrating AI tools into daily workflows and collaborating with them as part of the design process.

📝 Enhancement Note: The company culture values impact, data, and innovation. For operations professionals, this means a role where analytical thinking, process optimization, and a commitment to the company's mission are highly valued and integrated into daily work.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Choice and Clarity: Designing a search experience for a complex marketplace (therapists) with many options while preventing patient overwhelm.

• Translating Complex Data: Effectively communicating provider relevance and match explanations to users who may not fully understand the underlying algorithms.

• Rapid Experimentation Cycle: Adapting to a fast-paced environment where designs are continuously tested and iterated upon, requiring quick learning and adaptation.

• Evolving AI Landscape: Staying ahead of AI advancements and integrating them effectively into design workflows while maintaining high craft standards.

• Healthcare System Nuances: Designing within the specific constraints and opportunities of the healthcare and insurance landscape.

Learning & Development Opportunities:

• Advanced AI Design: Becoming a leader in using AI tools for product design and development.

• Conversion Rate Optimization (CRO): Deepening expertise in A/B testing, funnel analysis, and user behavior optimization.

• Product Strategy: Gaining experience in shaping the strategic direction of patient acquisition and onboarding.

• Cross-functional Acumen: Developing a strong understanding of product management, engineering, and data science principles.

• Healthcare Domain Expertise: Gaining in-depth knowledge of the mental healthcare provider and patient ecosystem.

📝 Enhancement Note: The challenges and growth opportunities are directly relevant to operations professionals seeking to leverage design thinking for business impact. The emphasis on CRO, data-driven strategy, and cross-functional understanding aligns perfectly with the development path for individuals in Revenue Operations, Sales Operations, or GTM Operations.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you owned a conversion-critical surface. What were the key metrics, what experiments did you run, and what was the outcome?" (Focus on A/B testing, data analysis, and iterative improvements.)

• "How would you approach designing a 'match explanation' feature for a provider search results page, considering a user who doesn't understand why they were recommended a particular therapist?" (Focus on user empathy, clear communication, and AI integration possibilities.)

• "Imagine the search results page has only two providers listed. How would your design approach differ from a scenario with forty providers? What are the core principles you'd apply?" (Focus on handling edge cases and maintaining user engagement.) Company & Culture Questions:

• "What interests you most about Headway's mission to improve mental healthcare access?" (Show genuine interest and alignment with the company's purpose.)

• "How do you see AI tools like Claude Code and Cursor fitting into the future of product design, and how have you used them in your previous work?" (Demonstrate practical experience and forward-thinking.)

• "Describe your experience working in a cross-functional pod. How do you ensure alignment and effective collaboration with PMs and Engineers?" (Highlight teamwork and communication skills.) Portfolio Presentation Strategy:

• Structure your Case Studies: Problem -> Your Role -> Process (including AI use) -> Solution -> Results (quantified impact) -> Learnings.

• Quantify Impact: Use numbers and data to demonstrate the success of your designs, especially regarding conversion rates and user engagement.

• Highlight Iteration: Show how you responded to data and feedback to improve designs over time.

• Discuss Trade-offs: Be prepared to talk about difficult decisions, compromises, and why certain features were prioritized or de-prioritized.

• Showcase AI Integration: Clearly explain how AI tools were used and what benefits they provided to your workflow or the final product.

📝 Enhancement Note: Interview preparation should heavily emphasize demonstrating an operations mindset: data-driven decision-making, process optimization, measurable impact, and cross-functional collaboration. Case studies that highlight these aspects will be most impactful.

📌 Application Steps

To apply for this Senior Product Designer position:

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

• Curate your Portfolio: Select 2-3 of your strongest case studies that best showcase your experience with conversion-critical surfaces, iterative design, A/B testing, and AI tool integration. Tailor the descriptions to highlight quantifiable results and your process.

• Optimize your Resume: Ensure your resume clearly highlights your years of experience, specific accomplishments in product design, and any experience with AI tools, marketplace dynamics, or healthcare technology. Use keywords from the job description.

• Prepare your Presentation: Practice walking through your portfolio case studies, focusing on clarity, conciseness, and articulating your process and impact. Be ready to discuss your approach to experimentation and data analysis.

• Research Headway: Understand their mission, product, and recent funding. Be prepared to discuss how your skills and experience can contribute to their goals, particularly in optimizing the patient acquisition funnel.

⚠️ 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.