Staff Product Designer, Group Practices

📍 Job Overview

Job Title: Staff Product Designer, Group Practices

Company: Headway

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

Job Type: FULL_TIME

Category: Product Design / GTM Operations Support

Date Posted: 2026-08-19

Experience Level: 10+ Years

Remote Status: On-site

🚀 Role Summary

• Lead product design initiatives for Headway's group practice segment, focusing on complex multi-user systems and 0-to-1 product development.

• Drive the end-to-end design experience for group practices, encompassing onboarding, supervisory billing, packaging, and practice management tools.

• Leverage AI-first design practices, utilizing tools like Claude Code and Cursor for rapid prototyping and development.

• Collaborate closely with Sales and Customer Success teams to translate deep customer insights into impactful product strategies and design decisions.

• Contribute to the evolution of Headway's design system and foster a culture of AI-driven design innovation.

📝 Enhancement Note: While the title is "Product Designer," the responsibilities and required experience strongly indicate a senior-level role focused on a specific business segment (Group Practices) that has significant Go-To-Market (GTM) implications. The emphasis on understanding revenue models, driving growth, and partnering with Sales/CS positions this role as having a strong operational and GTM support component, even within a design function. The AI-first approach is a significant differentiator for this role.

📈 Primary Responsibilities

• Own the complete design lifecycle for the group practice segment, from initial discovery and onboarding through to advanced practice management and administrative tooling.

• Spearhead the design and scaling of supervisory billing functionalities, creating seamless onboarding and activation experiences for supervisors and supervisees across all 50 states.

• Design robust administrative workflows, role-based views, multi-provider management capabilities, and practice-level analytics tailored for group practice owners and administrators.

• Adapt and customize platform-wide feature launches (e.g., packaging, identity verification) to meet the unique requirements and design considerations of group practices.

• Utilize AI-powered tools (e.g., Claude Code, Cursor) for rapid prototyping, ideation, and contributing to the codebase, defining patterns, behaviors, and quality standards.

• Act as a key liaison between the product design team and Sales/Customer Success, translating direct customer feedback and relationships into actionable product requirements and design iterations.

• Actively contribute to the development and maintenance of the design system, sharing AI design practices, prompts, and patterns with the broader design team to foster collective learning and efficiency.

📝 Enhancement Note: The responsibilities highlight a strategic ownership of a critical business segment, requiring not just design execution but also business acumen and cross-functional leadership, particularly in translating GTM insights into product. The AI component is central to the execution methodology.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating advanced product design capabilities and understanding of complex systems is paramount. The emphasis on AI tools suggests a comfort with technical environments, implying that degrees in Design, Computer Science, or related fields could be beneficial but are not strictly required.

Experience: 8+ years of progressive product design experience, with a substantial portion dedicated to designing for multi-user systems involving distinct roles, permissions, and workflows (e.g., administrators, operators, end-users). Proven experience in 0-to-1 product development, including validating business models and scaling new product lines from concept to maturity.

Required Skills:

• Extensive experience in product design, with a proven track record of designing for complex, multi-user SaaS platforms.

• Demonstrated ability in 0-to-1 product development, from concept validation to market launch and scaling.

• Strong business acumen, with the ability to connect design decisions directly to business outcomes and revenue generation.

• Expertise in visual and interaction design, covering both growth-oriented surfaces (onboarding, activation) and operational workflows (dashboards, tooling).

• Proficiency with AI prototyping tools such as Claude Code, Cursor, or similar, viewing AI as an integral part of the design workflow.

• Exceptional stakeholder management skills, with a proven ability to partner effectively with Sales, Customer Success, and other cross-functional teams.

• Experience designing for platforms or marketplaces where segment-specific needs must be balanced with overarching platform consistency. Preferred Skills:

• Experience in the healthcare technology or mental health sector.

• Familiarity with designing for financial or billing-related workflows within a B2B context.

• Contribution to or experience with established design systems.

• Understanding of agile development methodologies and experience working within cross-functional product teams.

• Data-driven design approach, utilizing analytics to inform design decisions and measure impact.

📝 Enhancement Note: The experience requirement is elevated to "10+" years by the AI's assessment, reflecting the "Staff" level designation and the breadth of responsibilities. The emphasis on business building and AI proficiency are key differentiators for this role, moving beyond traditional product design.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A curated selection of case studies demonstrating end-to-end product design ownership for complex, multi-user systems.

• Examples showcasing 0-to-1 product development, illustrating the journey from initial concept and validation through to scaled implementation and iteration.

• Case studies that highlight the candidate's ability to translate business objectives and revenue models into effective design solutions.

• Projects demonstrating experience in designing for platforms or marketplaces, with a clear articulation of how segment-specific needs were balanced with platform consistency.

• Visual and interaction design examples that showcase strong craft across both user acquisition (growth) and operational tooling surfaces. Process Documentation:

• Detailed walkthroughs of the design process employed for key projects, emphasizing how AI tools were integrated into ideation, prototyping, and development phases.

• Clear explanations of how user research, stakeholder feedback, and business requirements were synthesized into design decisions.

• Demonstrations of iterative design processes, including user testing methodologies and how feedback informed subsequent design iterations.

• Examples of how design contributed to defining new product lines or validating business models.

📝 Enhancement Note: The portfolio requirements are tailored to emphasize the unique aspects of this role: complex systems, business impact, and AI integration, which are critical for a "Staff" level designer with GTM responsibilities.

💵 Compensation & Benefits

Salary Range: $212,000 - $265,000 USD per year. This range is competitive for a Staff Product Designer role in major tech hubs like New York, San Francisco, and Seattle, reflecting the senior experience level, specialized focus on group practices, and the AI-first approach.

Benefits:

• Equity compensation, offering ownership and potential upside in a rapidly growing Series D company.

• Comprehensive health coverage: Medical, Dental, and Vision insurance plans.

• Health Savings Account (HSA) and Flexible Spending Account (FSA) for tax-advantaged healthcare expenses.

• 401K retirement savings plan.

• Work-from-Home Stipend to support a productive remote or hybrid setup.

• Therapy Reimbursement to support employee mental well-being.

• Generous 16-week parental leave for eligible employees.

• Carrot Fertility annual reimbursement and membership for fertility support.

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

• Flexible Paid Time Off (PTO) policy, allowing employees to manage their time off as needed.

• Employee Assistance Program (EAP) for confidential support services.

• Opportunities for training and professional development to foster continuous learning and career growth.

Working Hours: 40 hours per week, consistent with full-time employment. Given the on-site nature and the demands of a senior role, flexibility may be expected, but a standard 40-hour work week is the baseline.

📝 Enhancement Note: The salary range provided is directly from the job posting. The benefits list is comprehensive and tailored to attract senior talent, emphasizing both financial and well-being aspects. The working hours are inferred to be standard full-time, with potential for flexibility typical of senior roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology (HealthTech), specifically focused on mental healthcare access and provider enablement. Headway operates within a SaaS and marketplace model, aiming to disrupt traditional mental healthcare payment and access barriers.

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, fast-paced environment with established processes but still retaining startup agility.

Founded: Headway was founded with a mission to make mental healthcare accessible and affordable by streamlining insurance processes for providers. Its growth trajectory has been rapid, supported by significant venture capital funding.

Team Structure:

• The Staff Product Designer will be the "design anchor" for the "segment-based pod" focused on Group Practices, implying a dedicated, cross-functional team structure (pod) comprising design, product, engineering, and potentially GTM roles.

• This role reports into a design leadership function, contributing to the broader design team's strategy and culture.

• Close collaboration is expected with Sales and Customer Success teams, highlighting a strong GTM integration within the product development lifecycle. Methodology:

• AI-First Design: Headway emphasizes an "AI-first" approach where designers leverage AI tools (Claude Code, Cursor) extensively for prototyping, ideation, and code generation. Designers are expected to define patterns, behaviors, and quality standards rather than solely generating pixels from scratch.

• Data-Driven Product Development: Insights from Sales and Customer Success, combined with user research and platform analytics, are critical for informing product direction and design decisions.

• Iterative Development: The emphasis on rapid prototyping and testing with AI tools suggests an agile and iterative product development process.

Company Website: https://headway.co/

📝 Enhancement Note: The company context is derived from the provided description, highlighting its mission, funding stage, and industry. The "AI-first" methodology is a defining characteristic of their design practice and a key aspect for potential candidates to understand. The team structure is inferred from the "segment-based pod" and "design anchor" terminology.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a senior "Staff" level within the Product Design function, with a strategic focus on a critical business segment (Group Practices). It demands not only deep design expertise but also business acumen, product strategy input, and the ability to drive significant impact on growth and revenue. The role is akin to a Senior Product Manager with a design specialization, owning a customer segment.

Reporting Structure: The Staff Product Designer will likely report to a Head of Design or a Director of Product Design. They will work within a dedicated pod for Group Practices, collaborating closely with Product Managers, Engineers, and potentially GTM leads for that segment.

Operations Impact: The role has a direct impact on Headway's growth trajectory by designing experiences that attract, onboard, and retain group practices. Success in this role will translate to increased provider adoption, patient reach, and ultimately, revenue growth, by making the platform more valuable and scalable for group practice organizations.

Growth Opportunities:

• Leadership within a Segment: Opportunity to become the definitive design authority for the group practice segment, shaping its product roadmap and user experience.

• AI Design Specialization: Deepen expertise in AI-assisted design workflows, becoming a leader and advocate for these practices within the company and potentially the broader industry.

• Cross-Functional Influence: Develop stronger strategic partnerships with Sales, CS, and Product Management, gaining broader business understanding and influence.

• Mentorship and Team Contribution: Contribute to the design system, mentor junior designers, and help shape the design culture at a rapidly growing company.

• Potential for Design Management: As the company scales, this senior individual contributor role could serve as a stepping stone towards design management or lead design positions for larger product areas.

📝 Enhancement Note: The "Staff" designation signifies a senior individual contributor role with significant strategic influence and ownership, directly impacting GTM success through product design. The growth opportunities are framed around leadership, specialization, and broader business impact.

🌐 Work Environment

Office Type: Headway operates with an on-site work model in its listed locations (New York, San Francisco, Seattle). This suggests a collaborative office environment where in-person interaction is valued for team cohesion, brainstorming, and rapid problem-solving.

Office Location(s): The role is available in major tech hubs: New York City, NY; San Francisco, CA; and Seattle, WA. These locations offer vibrant ecosystems for tech professionals, access to talent, and proximity to industry events and networking opportunities.

Workspace Context:

• Collaborative Hub: The office environment is designed to foster collaboration, likely featuring open-plan workspaces, meeting rooms, and common areas conducive to spontaneous interactions and team syncs.

• Technology-Enabled: Expect access to modern office technology and tools, including robust IT support, high-speed internet, and potentially specialized hardware for design work. The company's AI-first approach implies a strong digital infrastructure and access to necessary software licenses.

• Cross-Functional Proximity: Being on-site facilitates direct and frequent interaction with product managers, engineers, sales representatives, and customer success managers, essential for the role's collaborative demands.

Work Schedule: While the standard is 40 hours per week, the on-site nature and senior level of the role may necessitate a degree of flexibility. Design teams often operate with agile methodologies, which can involve periods of intense focus and collaboration, especially during critical project phases.

📝 Enhancement Note: The "On-site" remote status dictates the work environment description. The emphasis is on the benefits of an in-office setting for collaboration and the specific context of Headway's tech-forward and AI-centric approach.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A call with a recruiter to assess general fit, experience, and interest in Headway's mission and the specific role.

• Design Portfolio Review: Presentation of a curated portfolio to the design team, focusing on case studies that demonstrate experience with multi-user systems, 0-to-1 product development, and business impact. Expect discussion on your design process, especially your use of AI tools.

• Hiring Manager Interview: Deep dive into your experience, particularly regarding designing for complex segments, business strategy integration, and leadership potential. This stage will likely assess your fit with the Group Practices pod and your ability to own a customer segment.

• Cross-Functional Interviews: Interviews with peers from Product Management, Engineering, Sales, and Customer Success to evaluate collaboration skills, communication style, and ability to translate GTM insights into product.

• Final Round / Executive Interview: Potentially a discussion with senior leadership to assess overall fit, strategic thinking, and alignment with Headway's mission and culture.

Portfolio Review Tips:

• Focus on Impact: Select 3-4 strong case studies that clearly demonstrate your problem-solving skills, design process, and measurable business outcomes. Prioritize projects involving multi-user systems or 0-to-1 initiatives.

• Highlight AI Integration: Be prepared to walk through how you utilized AI tools (Claude Code, Cursor) in your process. Showcase specific prompts, workflows, and how AI accelerated your work or led to innovative solutions.

• Showcase Business Acumen: Clearly articulate the business context for each project, the revenue model considerations, and how your design decisions directly contributed to business goals (e.g., growth, activation, retention).

• Address Segment Ownership: For this role, emphasize projects where you owned a specific customer segment or a complex product area, detailing how you managed diverse user needs and stakeholder requirements.

• Visual & Interaction Craft: Ensure your presentation showcases strong visual design principles and sophisticated interaction design, demonstrating your ability to create polished and effective user experiences.

Challenge Preparation:

• AI Prototyping Exercise: Be ready for a design challenge that may involve using AI tools to rapidly prototype a solution to a given problem, similar to what is expected in the role.

• Strategic Thinking: Prepare to discuss how you would approach designing for a complex segment like group practices, considering their unique workflows, administrative needs, and revenue models.

• Cross-Functional Collaboration Scenarios: Anticipate questions about how you would collaborate with Sales and CS, manage conflicting stakeholder priorities, and translate GTM feedback into design action.

📝 Enhancement Note: This section is tailored to the specific demands of a senior product designer role with a strong GTM component and an AI-first methodology. The advice focuses on demonstrating impact, AI proficiency, and strategic thinking relevant to owning a business segment.

🛠 Tools & Technology Stack

Primary Tools:

• AI Prototyping & Development: Claude Code, Cursor, MagicPatterns, or similar AI-powered design and coding tools are central to the workflow. Proficiency and a proactive approach to leveraging these tools are expected.

• Design Software: Figma or Sketch for core design and prototyping.

• Collaboration Tools: Slack for communication, Jira/Asana for project management.

Analytics & Reporting:

• Product Analytics: Tools like Amplitude, Mixpanel, or similar for understanding user behavior, tracking feature adoption, and measuring GTM impact.

• Data Warehousing/BI Tools: Potential exposure to tools like Looker, Tableau, or SQL for accessing and analyzing data that informs design decisions.

CRM & Automation:

• CRM: Salesforce or similar CRM platforms for understanding customer segments, sales pipelines, and customer success interactions.

• Workflow Automation: While not explicitly mentioned for designers, an understanding of how automation impacts user workflows within a SaaS product is beneficial.

📝 Enhancement Note: The technology stack is heavily influenced by the "AI-first" mandate, highlighting specialized AI tools. Other standard design and product development tools are also included, reflecting a modern tech environment.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to Headway's mission of making mental healthcare accessible and affordable. This value translates into a focus on user impact and problem-solving.

• AI-Centric Innovation: Embracing AI as a core tool for innovation, efficiency, and elevating the design practice. Encouraging experimentation and sharing of AI-driven workflows.

• Business Growth Focus: A clear understanding and drive towards business objectives, with design decisions directly contributing to user acquisition, activation, and revenue growth, particularly within the group practice segment.

• Collaboration and Transparency: Valuing open communication, cross-functional teamwork, and transparent sharing of insights and challenges across design, product, and GTM teams.

• User-Centricity with Pragmatism: Deep empathy for users (group practices, providers, patients) balanced with pragmatic decision-making that considers business constraints and scalability.

Collaboration Style:

• Pod-Based Teamwork: Working within dedicated, cross-functional pods focused on specific business segments (like Group Practices), fostering tight-knit collaboration with product managers and engineers.

• GTM Integration: A highly collaborative approach with Sales and Customer Success, treating them as key partners and sources of critical customer insights that directly inform product direction.

• Design System Contribution: Active participation in the design community, contributing to and leveraging the design system, and sharing best practices, especially around AI tools.

• Feedback-Rich Environment: Encouraging constructive feedback loops within the design team and across other disciplines to ensure high-quality output and continuous improvement.

📝 Enhancement Note: The culture and values are inferred from the company's mission, the "AI-first" approach, and the emphasis on business impact and cross-functional collaboration, especially with GTM teams.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of Multi-User Systems: Designing for diverse user roles (owners, admins, supervisors, supervisees) within group practices, each with unique needs, permissions, and workflows.

• Balancing Segment Needs with Platform Consistency: Ensuring that the unique requirements of group practices are met without compromising the overall platform's coherence and scalability for other user segments.

• Driving 0-to-1 Product Development: Taking new product concepts for group practices from initial ideation and validation through to a scaled, market-ready solution, often with ambiguous requirements.

• AI Tool Integration and Evolution: Staying at the forefront of AI design tools, effectively integrating them into workflows, and navigating the rapid evolution of AI capabilities in design.

• Translating GTM Insights: Effectively synthesizing and acting upon feedback from Sales and Customer Success, who have deep but sometimes disparate customer relationships, into actionable product design.

Learning & Development Opportunities:

• Deep Specialization: Becoming the go-to expert for group practice product design and strategy within Headway.

• AI Design Mastery: Developing cutting-edge skills in AI-assisted design and prototyping, potentially becoming a thought leader in this emerging field.

• Strategic Product Influence: Gaining significant experience in shaping product strategy and roadmap for a critical business segment, directly impacting company growth.

• Cross-Functional Acumen: Expanding business understanding by working closely with Sales, CS, and Product Management, enhancing strategic partnership capabilities.

• Mentorship and Design Leadership: Contributing to the growth and culture of the design team, with potential avenues for leading design initiatives or mentoring junior colleagues.

📝 Enhancement Note: Challenges are identified based on the role's specific focus (group practices, multi-user systems, AI) and the inherent complexities of scaling a platform. Growth opportunities are aligned with career progression for a senior individual contributor in a high-growth tech environment.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed for a complex multi-user system with distinct roles and permissions. What were the key challenges, and how did you ensure each user type had an optimal experience?" (Prepare to discuss your process, decision-making, and outcomes, highlighting group practice parallels.)

• "Walk us through a 0-to-1 product you designed. How did you validate the business model, what was your design process, and what was the ultimate impact?" (Focus on early-stage product development and business model validation.)

• "How do you see AI tools like Claude Code or Cursor changing the product design process? Provide specific examples of how you've used them, and what were the benefits and limitations?" (Be ready to demonstrate practical application and strategic thinking about AI in design.)

• "Imagine you're tasked with designing a new feature for group practices that needs to drive significant revenue growth. How would you approach this, considering input from Sales and Customer Success?" (Demonstrate your ability to connect design to business outcomes and GTM collaboration.) Company & Culture Questions:

• "Why Headway? What about our mission to improve mental healthcare access resonates with you?" (Show genuine interest in the company's purpose.)

• "How would you contribute to an 'AI-first' design culture? What are your thoughts on sharing AI prompts and patterns?" (Highlight your collaborative spirit and proactive approach to AI.)

• "How do you approach balancing the needs of a specific customer segment (like group practices) with the broader platform's consistency and scalability?" (Assess your strategic thinking and platform-level perspective.) Portfolio Presentation Strategy:

• Structure for Impact: Organize your presentation logically, starting with the business problem and user needs, followed by your process (including AI integration), key design decisions, and finally, the measurable outcomes.

• Quantify Success: Wherever possible, use data and metrics to demonstrate the impact of your designs. This is crucial for a role focused on business outcomes.

• Narrate Your Process: Don't just show screens; tell the story behind your designs. Explain why you made certain choices, what alternatives you considered, and how you iterated.

• Showcase AI in Action: Dedicate specific slides or sections to demonstrating your AI workflows. Show before/after, illustrate how AI accelerated your work, or how it enabled novel solutions.

• Engage and Converse: Treat the portfolio review as a conversation. Be ready to answer in-depth questions about your work and your design philosophy.

Challenge Preparation:

• Problem Framing: For any design challenge, start by clearly defining the problem, identifying key user personas, and outlining your assumptions.

• Rapid Prototyping: Practice using AI tools to quickly generate wireframes, mockups, or even interactive prototypes. Focus on speed and iteration.

• Justification: Be prepared to articulate the rationale behind every design decision, especially in the context of business goals and user needs.

📝 Enhancement Note: Interview preparation is geared towards a senior designer role with a strong emphasis on business impact, AI utilization, and segment ownership, reflecting the specific requirements of this position.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your application through the official Headway careers page linked in the job posting.

• Portfolio Customization: Tailor your portfolio to highlight projects involving complex multi-user systems, 0-to-1 product development, and demonstrated business impact. Explicitly showcase your experience with AI design tools and how they were integrated into your workflow.

• Resume Optimization: Ensure your resume clearly articulates your 8+ years of experience, focusing on achievements in product design for SaaS platforms, business model validation, and any experience with healthcare technology or marketplaces. Use keywords such as "Product Design," "SaaS," "AI Prototyping," "Multi-user Systems," and "0-1 Product Development."

• Interview Preparation: Thoroughly prepare for each stage of the interview process, practicing your portfolio presentation, anticipating strategic and behavioral questions, and being ready to discuss your approach to AI-assisted design and cross-functional collaboration.

• Company Research: Deeply research Headway's mission, its current product offerings for group practices, its market position, and its AI-first philosophy. Understand their business model and how product design contributes to their growth objectives.

⚠️ 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.