Senior Product Designer, Provider Acquisition

📍 Job Overview

Job Title: Senior Product Designer, Provider Acquisition

Company: Headway

Location: New York, NY, United States

Job Type: FULL_TIME

Category: Product Design, Growth Operations

Date Posted: 2026-08-03

Experience Level: 5-10 years

Remote Status: Fully Remote

🚀 Role Summary

• This role is focused on optimizing the provider acquisition funnel, a critical component of Headway's growth operations strategy, by designing user-centric experiences that drive conversion.

• You will be instrumental in designing both external-facing provider experiences and internal tooling, directly impacting the efficiency and effectiveness of the Provider Growth team.

• The position emphasizes an AI-first design approach, requiring proficiency in AI tools for prototyping and iteration, aligning with modern operations and product development practices.

• This is a high-leverage role within the Provider Acquisition pod, responsible for improving key performance indicators such as SQL to Intake-Complete conversion rates through data-driven design and experimentation.

📝 Enhancement Note: While the job title is "Senior Product Designer," the responsibilities and focus on funnel optimization, conversion rates, and internal tooling strongly align with a Growth Operations or Product Operations mindset within a GTM context. The emphasis on AI tools also points to a forward-thinking operations approach.

📈 Primary Responsibilities

• Lead the design strategy and execution for the provider rebrand and landing page, partnering with Creative to ensure a premium, high-converting provider-facing experience.

• Own the design of the lead/application entry point, focusing on creating a low-friction, high-trust, and conversion-optimized flow for prospective providers.

• Design and enhance Provider Growth Associate (PGA) enablement tools and agentic experiences, translating best-in-class playbooks into effective product features for real-time decision support.

• Drive funnel conversion by diagnosing SQL→Intake-Complete drop-off points, formulating hypotheses, and executing design experiments to move key metrics.

• Conduct user research with providers and PGAs, in collaboration with the research team, to inform design decisions and contribute new patterns to the Helix design system.

• Apply AI tools (e.g., Claude Code, Cursor, MagicPatterns) as a core part of the design workflow for rapid prototyping, iteration, and direct involvement in the development lifecycle.

• Collaborate closely with Product Management, Engineering, Creative, and Research teams to ensure cohesive and impactful product development.

• Contribute to raising the overall design craft bar within the organization and advocate for user-centered design principles across the acquisition pod.

📝 Enhancement Note: The responsibilities clearly outline a focus on conversion optimization and operational efficiency within the provider acquisition process, aligning with key GTM and Revenue Operations principles. The ownership of internal tooling also points to a significant operational impact.

🎓 Skills & Qualifications

Education:

• While no specific degree is listed, a Bachelor's degree in Design, Human-Computer Interaction, or a related field is often preferred for senior design roles. Equivalent practical experience will also be strongly considered. Experience:

• 5+ years of demonstrated experience in product design, with a significant portion focused on conversion optimization, growth initiatives, or acquisition funnels.

• Proven experience designing and launching features that directly impact key business metrics and user conversion. Required Skills:

• Exceptional visual and interaction design craft, with a portfolio showcasing polished, high-quality work for public-facing surfaces and attention to detail.

• Strong analytical mindset and ability to "think in funnels," diagnosing drop-off points and leveraging data to drive design decisions.

• Experience designing agentic or AI-powered workflows, including real-time decision support and intelligent automation.

• Proficiency in AI prototyping tools such as Claude Code, Cursor, and MagicPatterns, integrating them as core elements of the design workflow.

• Demonstrated ability to partner fluently across functions, particularly with Creative/Brand, Product Management, and Engineering.

• Experience conducting user research and translating insights into actionable design solutions.

• Familiarity with design systems and the ability to contribute to and leverage them effectively. Preferred Skills:

• Experience within the healthcare industry or a mission-driven, high-growth startup environment.

• Familiarity with A/B testing methodologies and experimentation frameworks.

• Experience designing for both B2C (provider-facing) and internal B2B (PGA tooling) applications.

• Understanding of front-end development principles to facilitate closer collaboration with engineering teams.

📝 Enhancement Note: The emphasis on AI tools, funnel analysis, and conversion metrics suggests that candidates with a background in growth marketing operations or product-led growth strategies would be highly valuable. The "agentic workflows" requirement points towards a need for understanding complex operational processes and how design can optimize them.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 2-3 case studies demonstrating significant experience in conversion optimization, growth design, or acquisition funnels.

• For each case study, clearly articulate the problem, your design process, the specific AI tools or methodologies used, the challenges encountered, and the quantifiable results achieved (e.g., increased conversion rates, reduced drop-off).

• Highlight examples of designing for both external-facing user journeys and internal operational tooling.

• Include examples of designs that leverage AI or agentic workflows to enhance user experience or operational efficiency.

• Demonstrate a strong understanding of visual hierarchy, interaction patterns, and the creation of high-fidelity prototypes. Process Documentation:

• Be prepared to discuss your design process in detail, including how you integrate user research, data analysis, and AI tools into your workflow.

• Describe how you approach diagnosing funnel drop-off and formulating hypotheses for design interventions.

• Explain your experience with A/B testing and experimentation in a product design context.

• Discuss your approach to collaborating with cross-functional teams (PM, Eng, Creative, Research) throughout the design and development lifecycle.

📝 Enhancement Note: The portfolio should clearly demonstrate the candidate's ability to impact key operational metrics through design. Case studies that quantify improvements in conversion, efficiency, or user activation will be highly regarded. The expectation for AI tool integration means portfolio pieces should ideally reflect this.

💵 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, reflecting industry benchmarks for senior-level design roles in high-cost-of-living areas like New York. Benefits:

• Equity compensation

• Medical, Dental, and Vision coverage

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

• 401K retirement plan

• Work-from-Home Stipend

• Therapy Reimbursement

• 16-week parental leave for eligible employees

• Carrot Fertility annual reimbursement and membership

• 13 paid holidays annually, plus a Holiday Break between December 25th and December 31st

• Flexible Paid Time Off (PTO)

• Employee Assistance Program (EAP)

• Training and professional development opportunities Working Hours:

• This is a full-time role. While standard working hours are typically 40 per week, the company emphasizes flexible PTO, suggesting a results-oriented work environment that values work-life balance. However, given the fast-paced startup environment and focus on conversion, proactive engagement and responsiveness are expected.

📝 Enhancement Note: The salary range is competitive for a Senior Product Designer role in a major US metropolitan area, especially for a well-funded Series D company. The comprehensive benefits package supports employee well-being and professional growth, which are crucial for retaining top talent in specialized roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology, Mental Healthcare, SaaS. Headway operates at the intersection of healthcare and technology, aiming to democratize access to mental health services by simplifying insurance complexities for providers and patients. This industry focus implies a mission-driven culture.

Company Size: Headway is a Series D funded company, indicating significant growth and a substantial employee base, likely ranging from 200-500+ employees. This size suggests a dynamic environment with established processes but still retaining startup agility.

Founded: Headway was founded with a mission to fix the mental healthcare system's accessibility issues. Its founding principles are centered around innovation, problem-solving, and social impact.

Team Structure:

• The Provider Growth team is a key component of Headway's Go-To-Market (GTM) strategy, focusing on acquiring and enabling mental health providers.

• This role is the first embedded design position within the Acquisition pod, indicating a growing need for specialized design expertise within this critical growth area.

• The design team is adopting an "AI-first" methodology, suggesting a forward-thinking and technologically adept team culture.

• Designers are expected to work closely with Product Managers, Engineers, Creative teams, and Researchers, fostering a highly collaborative and cross-functional environment. Methodology:

• Data-driven decision-making is central, with a focus on analyzing funnel metrics (SQL → Intake-Complete) and running experiments to optimize conversion.

• AI tools are integrated into the design workflow for rapid prototyping and iteration, reflecting a commitment to leveraging cutting-edge technology for efficiency.

• A strong emphasis is placed on user research to understand the needs of both providers and internal users (PGAs).

• Design is seen as a critical lever for growth and operational efficiency, not just an aesthetic component.

Company Website: https://headway.co/

📝 Enhancement Note: Headway's mission to improve mental healthcare accessibility creates a strong sense of purpose that likely permeates its culture. The company's growth stage suggests opportunities to shape processes and contribute significantly to its evolution, particularly within the Provider Acquisition function.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, indicating a mid-to-senior career stage. It requires a high degree of autonomy, strategic thinking, and the ability to mentor or influence others. The focus on acquisition and conversion aligns with growth operations, offering a path towards specializing in GTM optimization.

Reporting Structure: The role is embedded within the Provider Acquisition pod and will report to a design lead or Head of Design. Close collaboration with Product Management and Engineering leads within the pod is expected.

Operations Impact: This role has a direct and measurable impact on Headway's growth by increasing the number of providers on the platform. This directly translates to increased patient access to affordable mental healthcare, fulfilling the company's core mission. The design of internal tooling also enhances the operational efficiency of the Provider Growth Associates, further contributing to scalable growth.

Growth Opportunities:

• Skill Specialization: Deepen expertise in growth design, conversion optimization, AI-driven product development, and user research within a mission-critical GTM function.

• Leadership Potential: As the first embedded designer in the acquisition pod, there's an opportunity to shape design processes, mentor junior designers, and potentially grow into a design lead role for acquisition or related growth areas.

• Cross-Functional Development: Gain extensive experience working with Product, Engineering, Creative, and Data Science teams, broadening understanding of the entire product development lifecycle and GTM strategy.

• Industry Impact: Contribute to a rapidly evolving mental healthcare tech landscape, developing solutions that have a tangible positive impact on access to care.

📝 Enhancement Note: For operations professionals, this role offers a unique blend of product design and growth operations focus. The emphasis on metrics, conversion, and internal tooling makes it a compelling opportunity for those looking to apply design skills to solve operational challenges and drive business outcomes.

🌐 Work Environment

Office Type: The role is listed as "TELECOMMUTE" and "Fully Remote" within the United States. This indicates a distributed workforce where collaboration happens primarily through digital tools.

Office Location(s): While the role is remote, the salary range is benchmarked against New York, suggesting that candidates may be expected to be in or near a major metropolitan area, or that the company has a significant presence or talent pool there. However, the remote nature provides flexibility.

Workspace Context:

• Collaborative Environment: Expect a highly collaborative digital workspace, relying heavily on tools like Slack, Zoom, Figma, and project management software. Regular virtual team meetings, design critiques, and cross-functional syncs will be part of the routine.

• Tools and Technology: Access to a robust technology stack, including AI-powered design tools (Claude, Cursor, MagicPatterns), Figma for design and prototyping, and potentially other collaboration platforms.

• Operations Team Interaction: Frequent interaction with the Provider Growth Associates (PGAs) and their leadership, as well as with Product Managers and Engineers responsible for the acquisition funnel and internal tooling.

Work Schedule:

• This is a full-time position, typically requiring around 40 hours per week. The remote nature and flexible PTO policy suggest a degree of autonomy in managing one's schedule, provided that core working hours for collaboration and meetings are met. Responsiveness during US business hours, particularly for the New York timezone, is likely expected.

📝 Enhancement Note: For operations candidates, the fully remote aspect is a significant factor. It requires strong self-discipline, excellent asynchronous communication skills, and comfort with digital collaboration tools. The emphasis on AI tools suggests a modern, tech-forward remote work environment.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review your application and resume, looking for alignment with the core requirements (5+ years experience, conversion/growth focus, AI tool proficiency).

• Portfolio Review & Design Exercise: You will likely be asked to present your portfolio, focusing on case studies relevant to conversion, acquisition, or AI-driven workflows. A take-home design exercise or a live design challenge may be part of this stage, focusing on a problem related to the provider acquisition funnel.

• Cross-Functional Interviews: Interviews with Product Management, Engineering, and potentially Creative leads to assess collaboration skills, technical understanding, and alignment with the team's methodology.

• Hiring Manager Interview: A final interview with the hiring manager to discuss strategic fit, career aspirations, and overall alignment with Headway's mission and culture.

Portfolio Review Tips:

• Quantify Impact: For each case study, clearly state the problem, your role, the actions taken (especially how AI was used), and the measurable outcomes (e.g., X% increase in conversion, Y% reduction in drop-off).

• Showcase AI Integration: Explicitly detail how you used AI tools (Claude, Cursor, MagicPatterns) in your process – for ideation, prototyping, code generation, or iteration.

• Focus on Funnel Thinking: Demonstrate your understanding of user funnels and how your design decisions directly addressed specific drop-off points or conversion barriers.

• Highlight Collaboration: Be prepared to discuss how you collaborated with PMs, engineers, and other stakeholders to bring your designs to life.

• Craft and Detail: Ensure your portfolio is polished, well-organized, and clearly communicates your design rationale and craft.

Challenge Preparation:

• Understand the Funnel: Research Headway's business model and the provider acquisition funnel. Think about potential friction points for providers signing up.

• AI Tool Familiarity: Be ready to discuss your experience with AI design tools and how you envision using them in this role.

• Growth & Conversion Mindset: Prepare to discuss strategies for improving conversion rates and driving growth through design.

• Agentic Workflows: Consider how AI or automated systems can assist or guide users (in this case, PGAs or providers) through complex processes.

📝 Enhancement Note: Candidates should prepare to demonstrate not just design skills but also a strong understanding of business metrics, operational efficiency, and the practical application of AI in a product development context. The portfolio is critical for showcasing these abilities.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (primary tool for UI design, prototyping, and collaboration).

• AI Design & Prototyping Tools: Claude Code, Cursor, MagicPatterns (essential for this role, used for rapid prototyping, iteration, and potentially code generation/assistance).

• Collaboration: Slack (real-time communication), Zoom (video conferencing), Google Workspace (documentation, spreadsheets).

• Project Management: Likely tools like Asana, Jira, or similar platforms for tracking design tasks and project progress.

Analytics & Reporting:

• Data Analysis: Tools for analyzing funnel metrics (SQL → Intake-Complete), identifying drop-off points, and measuring experiment results. This could include SQL queries, internal dashboards, or specialized analytics platforms.

• Experimentation Platforms: Tools for running A/B tests and other design experiments.

CRM & Automation:

• CRM: While not directly a design tool, understanding the CRM used by the Provider Growth team (e.g., Salesforce, HubSpot) would be beneficial for designing integrated tooling.

• Internal Tooling: The role involves designing internal agentic tooling for Provider Growth Associates (PGAs), which may interact with CRM data or other operational systems.

📝 Enhancement Note: Proficiency with Figma is standard for product designers. However, the explicit requirement for AI prototyping tools like Claude, Cursor, and MagicPatterns is a key differentiator for this role and should be highlighted by applicants. Understanding how design integrates with data analytics and operational workflows is also crucial.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to Headway's mission of making mental healthcare accessible, influencing design decisions to prioritize user impact.

• AI-First & Innovative: Embracing AI as a core tool for design and development, fostering a culture of continuous learning and adoption of new technologies.

• Data-Informed: Utilizing data and experimentation to validate design hypotheses and measure the impact of design solutions on key business metrics.

• Collaborative & Cross-Functional: Valuing strong partnerships across Product, Engineering, Creative, and Research teams to achieve shared goals.

• User-Centric: Deep empathy for both providers and internal users, ensuring that designs are intuitive, efficient, and solve real problems.

• Detail-Oriented: A commitment to high craft and attention to detail in all aspects of design, from visual aesthetics to interaction flow and functional implementation.

Collaboration Style:

• Asynchronous Communication: Given the remote nature, effective asynchronous communication via Slack and documentation is paramount.

• Proactive Engagement: Designers are expected to be proactive in seeking feedback, sharing work, and collaborating with team members.

• Design Critiques: Regular participation in design reviews and critiques to provide and receive constructive feedback.

• Cross-Functional Syncs: Active participation in meetings with Product, Engineering, and other teams to ensure alignment and shared understanding.

• Shared Ownership: A culture of shared ownership for product outcomes, where design plays a key role in driving success.

📝 Enhancement Note: The emphasis on AI and data-driven approaches suggests a team that is both innovative and results-oriented. Candidates should be prepared to articulate how their values align with these principles and how they contribute to a collaborative, mission-focused environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing External & Internal Design: Simultaneously designing for external provider-facing experiences and internal PGA tooling requires understanding different user needs and contexts.

• Driving Conversion: Optimizing complex funnels with multiple touchpoints and user types presents an ongoing challenge that requires continuous experimentation and iteration.

• AI Integration at Scale: Effectively integrating AI tools into the design workflow and ensuring they genuinely enhance efficiency and outcomes requires thoughtful application and continuous learning.

• Cross-Functional Alignment: Ensuring seamless collaboration and alignment with diverse teams (especially Creative and Engineering) on complex projects can be challenging in a fast-paced environment.

• Rapid Iteration: The nature of growth-focused roles often involves rapid iteration and experimentation, which can be demanding but also rewarding.

Learning & Development Opportunities:

• Specialization in Growth Design: Develop deep expertise in conversion rate optimization (CRO), A/B testing, and growth hacking through practical application.

• AI in Design Mastery: Become a leader in leveraging AI tools for design and prototyping, staying at the forefront of this rapidly evolving field.

• Healthcare Tech Domain Expertise: Gain in-depth knowledge of the mental healthcare industry and its unique operational and user challenges.

• Product Strategy Influence: Contribute significantly to the product strategy for provider acquisition, influencing roadmap decisions through data-driven design insights.

• Mentorship and Leadership: As the first embedded designer, there's an opportunity to shape best practices and potentially mentor future team members.

📝 Enhancement Note: This role offers significant opportunities for professional growth by pushing boundaries in AI-assisted design and conversion optimization within a high-impact industry. Candidates should highlight their proactive approach to learning and problem-solving.

💡 Interview Preparation

Strategy Questions:

• "How would you approach redesigning our provider lead form to improve conversion rates, given our AI-first approach?" (Focus on funnel analysis, AI tool usage, A/B testing).

• "Describe a time you used data to diagnose a drop-off in a user funnel and how your design intervention addressed it. What were the results?" (Quantifiable impact, process, metrics).

• "How do you see AI tools like Claude or Cursor enhancing the design process for agentic workflows? Provide an example." (Practical application of AI, understanding of agentic systems).

• "Walk us through a challenging cross-functional collaboration you experienced. How did you navigate disagreements and ensure project success?" (Collaboration, communication, problem-solving). Company & Culture Questions:

• "What excites you about Headway's mission to improve mental healthcare access?" (Mission alignment, personal connection).

• "How do you see your design philosophy aligning with an 'AI-first' team culture?" (Adaptability, tech-savviness, integration).

• "How do you approach user research for both external users and internal tooling stakeholders?" (Empathy, methodology, breadth of experience).

• "Describe your experience working in a fast-paced, growth-stage startup environment." (Resilience, adaptability, impact focus). Portfolio Presentation Strategy:

• Structure: Organize your presentation logically: Problem -> Your Role -> Process (including AI usage) -> Solution -> Results (quantified).

• Quantify Everything: For each case study, clearly state the key metrics you influenced and the percentage of improvement.

• Show, Don't Just Tell: Use visuals effectively to demonstrate your design solutions, user flows, and prototypes.

• Highlight AI Integration: Explicitly point out where and how you leveraged AI tools in your workflow.

• Tell a Story: Engage your audience by framing your projects as narratives with clear challenges, strategic decisions, and impactful outcomes.

• Be Ready for Deep Dives: Anticipate questions about specific design choices, trade-offs, and your reasoning behind them.

📝 Enhancement Note: Preparation should focus on demonstrating a blend of design craft, analytical rigor, operational understanding, and enthusiasm for Headway's mission. Emphasizing experience with conversion, growth, and AI tools will be key.

📌 Application Steps

To apply for this Senior Product Designer position:

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

• Portfolio Customization: Tailor your portfolio to highlight 2-3 case studies specifically demonstrating your experience in conversion optimization, growth design, or acquisition funnels. Clearly articulate your role, process (including AI tool usage), and quantifiable results.

• Resume Optimization: Ensure your resume clearly states your years of experience (5+ years), emphasizes your focus on conversion, growth, or acquisition, and mentions your proficiency with AI prototyping tools and design systems. Use keywords from the job description.

• Interview Preparation: Practice articulating your design process, your approach to funnel analysis, and how you leverage AI tools. Prepare compelling answers for strategy and behavioral questions, drawing from your portfolio examples.

• Company Research: Thoroughly research Headway's mission, product, and recent news. Understand their target audience (providers) and the challenges they aim to solve. Be prepared to discuss how your design contributions align with their goals.

⚠️ 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.