Senior / Staff Product Designer - Provider

📍 Job Overview

Job Title: Senior / Staff Product Designer - Provider

Company: Headway

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

Job Type: FULL_TIME

Category: Product Design (Provider Experience)

Date Posted: 2026-08-14

Experience Level: 5+ years (Senior) / 8+ years (Staff)

Remote Status: On-site

🚀 Role Summary

• Lead the end-to-end design of provider-facing products, focusing on streamlining complex workflows such as credentialing, scheduling, clinical documentation, and billing for mental healthcare providers.

• Champion an AI-native design approach, leveraging tools like Claude Code and Cursor for rapid prototyping, ideation, and shipping code-based improvements.

• Drive product strategy and roadmap influence through a combination of deep customer empathy, data-driven experimentation, and strong design rationale.

• Contribute to and evolve Headway's design system, 'Helix,' ensuring consistency and scalability across the provider platform.

• Mentor junior designers and elevate the overall craft and practice of the design team, particularly in AI-native methodologies.

📝 Enhancement Note: While the job title is "Product Designer," the responsibilities, required skills, and company focus heavily lean into operations and process optimization within the healthcare tech domain. This role is crucial for improving the operational efficiency of healthcare providers by designing user-friendly tools that automate administrative tasks. The emphasis on AI and code-based prototyping suggests a highly technical and forward-thinking design function critical for GTM and operational success.

📈 Primary Responsibilities

• Own the entire product lifecycle for provider-facing features, from initial problem framing and user research to launch, iteration, and performance measurement.

• Develop and implement AI-native design patterns and workflows, particularly for agentic documentation, intelligent billing automation, and replacing manual provider processes.

• Collaborate intensely with Product Managers, Engineers, and Researchers to define scope, prioritize initiatives, and ensure successful product delivery.

• Design and conduct experiments to validate hypotheses, measure task completion rates, reduce error rates, and improve overall provider satisfaction.

• Translate complex, high-stakes provider workflows into intuitive, efficient, and reliable user experiences.

• Contribute to the growth and maintenance of the 'Helix' design system, documenting new patterns and AI prompts for team-wide adoption.

• For Staff Designers: Lead 0→1 product initiatives, set design standards for AI-native practices, and mentor other designers to enhance team capabilities and craft.

📝 Enhancement Note: The responsibilities highlight a deep dive into operational efficiency for healthcare providers. Tasks like "credentialing, scheduling, clinical documentation, and billing" are core operational functions. The emphasis on AI for automation and efficiency directly aligns with GTM and operational goals of reducing overhead and improving user throughput for providers.

🎓 Skills & Qualifications

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

Experience:

• Senior: 5+ years of professional product design experience, with a demonstrated track record of delivering impactful B2B or professional tools.

• Staff: 8+ years of professional product design experience, including significant experience in 0→1 product development and designing AI-powered workflows.

Required Skills:

• Portfolio: A robust portfolio showcasing strong design craft, structured thinking, systems thinking, and measurable business impact.

• AI Prototyping: Fluency with AI prototyping tools (e.g., Claude Code, Cursor) and experience treating AI as a primary tool in the design process.

• B2B/Professional Tools: Experience designing for expert users who prioritize efficiency, reliability, and deep workflow integration.

• Systems Thinking: Ability to conceptualize and design complex, state-heavy workflows and multi-actor systems.

• Product Strategy: Strong product sense, with the ability to contribute to roadmap definition and shape product direction based on customer insights and strategic vision.

• Experimentation: Proven experience designing and running A/B tests and multi-sprint experiment arcs against clear success metrics.

• Cross-functional Collaboration: Excellent communication and collaboration skills to partner effectively with PMs, Engineering, and Research.

Preferred Skills:

• Experience designing agentic or AI-driven workflows (e.g., automated clinical documentation, intelligent billing).

• Contributions to or experience with design systems.

• Experience in the healthcare technology sector, particularly with provider-facing software.

• Mentorship experience (for Staff level).

• Experience designing for scalability and high-volume usage.

📝 Enhancement Note: The required skills are heavily weighted towards operational efficiency drivers: systems thinking, B2B/professional tools, and AI prototyping for automation. The portfolio requirement emphasizes measurable business impact, which is a key metric in operations and GTM roles.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end ownership of complex product surfaces, demonstrating problem framing, user research, ideation, prototyping, and iteration.

• Include case studies detailing the design of B2B or professional tools that improved user efficiency and achieved measurable business outcomes.

• Highlight your process for leveraging AI tools (Claude Code, Cursor) in your design workflow, showing how AI contributed to rapid prototyping and solution development.

• Demonstrate your ability to design for complex, stateful workflows and systems, illustrating how you managed intricate user journeys.

• Present examples of how you've used experimentation and data analysis to inform design decisions and measure success. Process Documentation:

• Clearly articulate your design process, emphasizing how you approach problem-solving, user research, and iterative development.

• Detail your methodology for collaborating with cross-functional teams, including PMs, engineers, and researchers, throughout the product development lifecycle.

• Illustrate your approach to creating and maintaining design systems, showing how you ensure consistency and scalability.

• Provide examples of how you measure the impact of your designs, focusing on metrics related to efficiency, task completion, error reduction, and user satisfaction.

📝 Enhancement Note: The portfolio requirements are designed to assess a candidate's ability to solve operational challenges through design. The emphasis on AI, B2B tools, and measurable impact directly reflects the operational nature of this role and the company's focus on efficiency.

💵 Compensation & Benefits

Salary Range:

• Senior: $180,000 - $225,000 per year (Base Salary)

• Staff: $212,000 - $265,000 per year (Base Salary)

Benefits:

• Equity compensation

• Medical, Dental, and Vision coverage

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

• 401K 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 (December 25th - 31st)

• Flexible Paid Time Off (PTO)

• Employee Assistance Program (EAP)

• Training and professional development opportunities

Working Hours: 40 hours per week (Standard full-time)

📝 Enhancement Note: The salary ranges provided are competitive for Senior and Staff Product Designer roles in major tech hubs like New York, San Francisco, and Seattle. The benefits package is comprehensive, supporting employee well-being and professional growth, which are important for retaining talent in specialized operational and design roles. The role is listed as "On-site," implying a standard 40-hour work week, though flexibility may exist within teams.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology (Mental Health Tech)

Company Size: Series D company with significant funding ($325M+), indicating a growth-stage company with established operations and a growing team. Headway's employee count is likely in the hundreds, suggesting a structured but agile environment.

Founded: Headway was founded to address a critical gap in mental healthcare accessibility by tackling insurance barriers. Its mission is to build a new, accessible mental healthcare system.

Team Structure:

• The design team operates with an AI-first methodology, integrating AI tools like Claude Code and Cursor directly into the design and prototyping workflow.

• Designers are embedded within product teams, partnering closely with Product Managers, Engineers, and Researchers to drive product outcomes.

• The team emphasizes cross-functional collaboration, with designers influencing roadmap priorities and product direction.

• There's a clear distinction between Senior and Staff roles, with Staff designers expected to mentor, set standards, and lead broader initiatives. Methodology:

• AI-Native Design: AI is treated as a core tool for prototyping, ideation, and even code generation, with designers focusing on defining patterns, behaviors, and quality.

• Data-Driven Experimentation: A strong emphasis on running experiments, measuring key metrics (task completion, error rates, satisfaction), and learning from both positive and negative results.

• Systems Thinking: A focus on designing for complex, state-heavy workflows and understanding the broader system implications of design decisions.

• Customer Obsession: Deep focus on understanding provider workflows and pain points to build tools that genuinely improve their practice efficiency and patient care.

Company Website: https://headway.co/

📝 Enhancement Note: Headway's culture is characterized by its mission-driven approach, technological innovation (AI-first), and a structured yet collaborative team environment. For operations-minded designers, this means working in an environment that values efficiency, data-informed decisions, and impactful product development within a critical sector.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a senior to staff level within the product design function, specifically focusing on a critical operational area for Headway: the provider experience. It’s not a traditional "operations" role but deeply impacts operational efficiency. Designers at this level are expected to take significant ownership, drive strategic initiatives, and contribute to the overall product direction.

Reporting Structure: Designers will likely report to a Design Lead or Head of Design, while working day-to-day within cross-functional product teams. Staff designers will also take on mentorship responsibilities and influence broader design team practices.

Operations Impact: The work of these designers directly impacts Headway's operational scalability and effectiveness. By improving the provider experience and automating administrative tasks through design, they enable more providers to use the platform, onboard more patients, and reduce operational overhead for both Headway and the providers. This role is crucial for driving the company's mission and business growth by optimizing the core platform for its users.

Growth Opportunities:

• Skill Development: Deepen expertise in AI-native design practices, complex B2B workflow design, and product strategy within the healthcare tech space.

• Leadership: For Staff Designers, opportunities to mentor, set design standards, and influence the broader design organization's methodology and culture.

• Impact: Drive significant improvements in provider operational efficiency, directly contributing to Headway's mission of making mental healthcare accessible.

• Career Progression: Potential to move into Principal Designer roles, lead larger product areas, or transition into management roles within the design organization.

📝 Enhancement Note: The career path emphasizes strategic impact and leadership within the design function, directly influencing operational outcomes. The growth opportunities are tied to advanced design skills, AI proficiency, and leadership within a mission-critical, high-growth company.

🌐 Work Environment

Office Type: The role is described as "On-site," indicating a physical office presence in New York, San Francisco, or Seattle. This suggests a collaborative office environment designed to foster teamwork and innovation.

Office Location(s): Headway has offices in New York, San Francisco, and Seattle, offering candidates flexibility in location. These are major tech hubs with established infrastructure and accessibility.

Workspace Context:

• Collaborative Environment: The emphasis on cross-functional teams and an AI-first methodology implies a workspace that encourages frequent interaction, brainstorming, and shared problem-solving.

• Technology & Tools: Designers will have access to cutting-edge AI tools (Claude Code, Cursor) and likely a robust design system (Helix), supported by the company's significant funding.

• Team Interaction: Opportunities to engage with diverse teams (PM, Engineering, Research) on a daily basis, fostering a dynamic and intellectually stimulating work environment.

Work Schedule: While the role is full-time (40 hours/week), the "On-site" nature combined with a mission-driven culture and focus on rapid iteration may suggest a dynamic work pace. However, the comprehensive benefits like Flexible PTO indicate a commitment to work-life balance.

📝 Enhancement Note: The on-site requirement points to a traditional office setup, likely with modern amenities to support collaborative design work. The integration of AI tools suggests a technologically advanced workspace.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess alignment with the role's requirements and experience level.

• Design Exercise/Challenge: Likely a take-home or live exercise focused on solving a complex provider workflow problem, potentially involving AI-driven solutions or system design. Candidates may be asked to prototype in code or present a detailed process.

• Portfolio Review & Case Studies: In-depth discussion of your portfolio, focusing on specific case studies that demonstrate your craft, strategic thinking, AI proficiency, and impact on business outcomes. Expect questions about your process, decision-making, and collaboration.

• Cross-functional Interviews: Meetings with Product Managers, Engineers, and Researchers to assess your collaboration style, communication skills, and ability to influence product direction.

• Staff-Level Interviews: For Staff candidates, expect discussions focused on leadership, mentorship, strategic influence, and experience with 0→1 product development.

Portfolio Review Tips:

• Curate Strategically: Select 2-3 projects that best showcase your ability to design for complex B2B workflows, leverage AI tools, drive measurable impact, and demonstrate systems thinking.

• Focus on Process & Impact: Clearly articulate the problem, your role, your process (especially AI integration), your design decisions, and the quantifiable results achieved. Use metrics to demonstrate business impact.

• Showcase AI Fluency: Dedicate a section or highlight within your case studies how you utilized AI tools for prototyping, ideation, or even code generation, explaining the benefits and your approach.

• Tell a Story: Structure your case studies to tell a compelling narrative about the problem, your journey to a solution, and the ultimate outcome.

• Be Prepared for Code: Given the AI-native requirement, be ready to discuss or even demo code snippets if your prototyping involved them.

Challenge Preparation:

• Understand Provider Workflows: Research common pain points and operational challenges for mental healthcare providers (credentialing, billing, scheduling, documentation).

• Think AI-First: Approach any challenge with an AI-native mindset. How can AI automate, augment, or transform the workflow?

• Systems Thinking: Consider the broader system implications of your proposed solution. How does it interact with other parts of the Headway platform or provider's practice?

• Metrics-Driven: Identify key metrics for success and be prepared to explain how you would measure the impact of your proposed solution.

📝 Enhancement Note: The interview process is designed to rigorously assess a candidate's operational design skills, AI proficiency, and strategic thinking. The portfolio and challenge preparation should directly address these core requirements.

🛠 Tools & Technology Stack

Primary Tools:

• AI Prototyping Tools: Claude Code, Cursor (or similar AI-powered coding/prototyping environments). Proficiency here is crucial.

• Design & Prototyping Software: Figma, Sketch, or similar industry-standard tools for wireframing, UI design, and interactive prototyping.

• Design System: 'Helix' (Headway's internal design system). Familiarity with contributing to or working within design systems is a plus.

Analytics & Reporting:

• Experience with product analytics tools (e.g., Amplitude, Mixpanel, Google Analytics) to understand user behavior and measure experiment results.

• Familiarity with data analysis to inform design decisions and quantify impact. CRM & Automation:

• While not a direct CRM role, understanding how product design impacts user journeys within SaaS platforms that may have CRM elements is beneficial. The focus is on automating provider workflows, which aligns with operational efficiency goals.

• Familiarity with workflow automation principles.

📝 Enhancement Note: The explicit mention of Claude Code and Cursor highlights a significant emphasis on AI-driven design and development. This is a key differentiator for this role and would be a critical area for candidates to prepare for.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to making mental healthcare accessible and affordable, which permeates all decision-making.

• AI-First Innovation: Embracing cutting-edge AI technologies to solve complex problems and drive efficiency.

• Customer Obsession: Deeply understanding and prioritizing the needs of mental healthcare providers to build exceptional tools.

• Data-Informed Decisions: Relying on experimentation, metrics, and user research to guide product development and validate impact.

• Efficiency & Reliability: Designing solutions that are not only user-friendly but also robust, fast, and reliable for professional use.

Collaboration Style:

• Cross-functional Partnership: Designers are integral members of product teams, working closely with PMs, Engineers, and Researchers to define strategy and execute on initiatives.

• Open Critique & Feedback: A culture that encourages constructive feedback through design critiques and team discussions to elevate craft and product quality.

• Knowledge Sharing: A commitment to sharing best practices, AI prompts, and design patterns across the team to foster collective growth and maintain consistency.

• Bias for Action: An environment that encourages rapid iteration, experimentation, and shipping to learn quickly.

📝 Enhancement Note: The culture emphasizes innovation, impact, and a collaborative, data-driven approach to problem-solving, which are all hallmarks of successful operations and GTM environments.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Expert Users: Creating intuitive interfaces for highly skilled professionals who demand efficiency and reliability, without oversimplifying complex workflows.

• AI Integration Complexity: Effectively integrating AI into existing or new workflows to provide genuine value, not just novelty, and managing the inherent complexities of AI-driven solutions.

• Balancing Innovation and Scale: Developing novel AI-native features while ensuring they are scalable, reliable, and maintainable within Headway's growing platform.

• Measuring AI Impact: Developing robust metrics and methodologies to quantify the ROI and effectiveness of AI-driven design solutions.

Learning & Development Opportunities:

• AI Design Mastery: Becoming a leader in AI-native product design, mastering tools and techniques that are at the forefront of the industry.

• Healthcare Tech Expertise: Gaining deep knowledge of the mental healthcare industry's operational challenges and regulatory landscape.

• Product Strategy Leadership: Contributing to and influencing the strategic direction of a rapidly growing healthcare technology company.

• Mentorship & Craft Elevation: For Staff Designers, opportunities to shape the design team's practices and mentor emerging talent.

📝 Enhancement Note: The challenges are directly related to operational efficiency and technological innovation, offering significant opportunities for professional growth in specialized areas of design and operations.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex B2B workflow you've designed. How did you approach understanding the user's needs and ensuring efficiency?" (Focus on structured thinking, user empathy, and operational impact.)

• "How do you see AI transforming product design for professional tools? Walk me through a hypothetical AI-native feature for mental health providers." (Highlight AI fluency, creative problem-solving, and understanding of operational automation.)

• "Tell me about a time you used experimentation to significantly improve a product metric. What was your process, and what did you learn?" (Demonstrate data-driven decision-making and iterative design for operational improvement.) Company & Culture Questions:

• "What interests you about Headway's mission to make mental healthcare accessible?" (Show genuine alignment with the company's purpose.)

• "How do you approach collaboration with PMs and Engineers, especially when influencing product strategy or roadmap?" (Illustrate teamwork and strategic influence.)

• "How do you ensure your designs are not only user-friendly but also contribute to measurable business outcomes like efficiency or cost reduction?" (Connect design work to operational and GTM success.) Portfolio Presentation Strategy:

• Structure for Impact: For each case study, clearly define the problem, your role, the user, your process (especially AI integration), your solutions, and the measurable results.

• Quantify Everything: Use numbers and data to demonstrate the impact of your work. For example, "Reduced task completion time by X%", "Decreased error rate by Y%", "Increased provider adoption by Z%."

• Highlight AI Use: Explicitly point out where and how AI tools were used in your process and the benefits they provided (e.g., faster prototyping, novel solutions).

• Showcase Systems Thinking: Explain how your design fits into the larger ecosystem and addresses complex interdependencies.

• Be Ready for Code: If your prototypes involved code, be prepared to discuss the technical aspects and how they informed your design.

📝 Enhancement Note: Interview preparation should focus on demonstrating a deep understanding of operational challenges, AI capabilities, and how design can drive efficiency and business impact within a mission-driven context.

📌 Application Steps

To apply for this Senior/Staff Product Designer position:

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

• Tailor your resume: Highlight experience with B2B tools, AI prototyping, systems thinking, and quantifiable achievements related to efficiency or user productivity.

• Curate your portfolio: Select 2-3 key projects that showcase your end-to-end design process, AI tool usage, and measurable impact on operational workflows. Ensure case studies clearly articulate the problem, your solution, and the results.

• Prepare for AI-specific discussions: Be ready to talk about your experience with tools like Claude Code and Cursor, and how you approach AI-native design challenges.

• Research Headway: Understand their mission, product, and the operational challenges they are solving in the mental healthcare space. Prepare thoughtful questions about their AI strategy and provider experience.

⚠️ 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.

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