Director, UX Research & Customer Insight

📍 Job Overview

Job Title: Director, UX Research & Customer Insight

Company: Headway

Location: New York, NY, USA (Remote OK)

Job Type: Full-Time

Category: UX Research

Date Posted: 2025-06-05

Experience Level: 5-10 years

Remote Status: Remote OK

🎨 Role Summary

• Lead and develop a world-class team of researchers to drive strategic decisions across Headway's business.
• Balance different research methodologies to address business needs and establish scalable customer insight artifacts.
• Cross-functional leadership for cultivating customer-centric culture and programs.
• Translate business questions into actionable research plans and present impactful insights to leadership.

🖼️ Primary Responsibilities

• Lead and develop a team of researchers with diverse expertise, including qualitative and quantitative research, UX research, market research, and clinical research, as well as program managers.
• Cross-functional leadership for cultivating customer-centric culture and programs: Voice of Customers, Touch Grass, Dogfooding.
• Operational excellence in establishing repeatable team processes and forums to facilitate the sharing of insights.
• Balance different research and experiment methodologies to address business needs.
• Implement and oversee a centralized research repository for knowledge sharing.
• Establish scalable and foundational customer insight artifacts: including persona, JTBD, customer journeys, etc.
• Select and manage key research tools and platforms (UserTesting, Qualtrics, etc.).
• Drive research initiatives that inform executive decision-making and product strategy with senior ICs.
• Translate business questions into actionable research plans.
• Present impactful insights to leadership, highlighting strategic implications.

🎓 Skills & Qualifications

Education: Bachelor's degree in a relevant field (e.g., Psychology, Anthropology, Human-Computer Interaction, or a related discipline) or equivalent experience.

Experience: 5+ years of experience as a people manager with a track record of building and leading high-performing teams that have effectively delivered business outcomes through technical investments. 5+ years of experience as an IC researcher in a company with mature research practices.

Required Skills:

• Proven leadership and management skills with experience building and leading high-performing teams.
• Strong product mindset with experience driving customer-centric culture and programs.
• Executive presence with the ability to communicate research value to C-suite and board-level stakeholders.
• Experience driving Voice of Customer or customer sentiment measured programs.
• Proven ability to balance different research methodologies to address business needs.
• Experience with research tools and platforms (UserTesting, Qualtrics, etc.).
• Familiarity with customer insight artifacts (persona, JTBD, customer journeys, etc.).

Preferred Skills:

• Master's degree or Ph.D. in a relevant field.
• Experience with specific research tools and platforms (e.g., UserTesting, Qualtrics, etc.).
• Familiarity with specific research methodologies (e.g., user interviews, surveys, usability testing, etc.).

🎨 Portfolio & Creative Requirements

Portfolio Essentials:

• Demonstrate experience leading and managing research teams, including qualitative and quantitative research, UX research, market research, and clinical research, as well as program managers.
• Showcase examples of driving research initiatives that informed executive decision-making and product strategy.
• Highlight experience with specific research tools and platforms (e.g., UserTesting, Qualtrics, etc.).
• Include examples of customer insight artifacts (persona, JTBD, customer journeys, etc.) created and used in previous roles.

Process Documentation:

• Provide detailed documentation of research methodologies used in previous roles, including user interviews, surveys, usability testing, etc.
• Include examples of how research findings were translated into actionable insights and presented to stakeholders.

💵 Compensation & Benefits

Salary Range: $255,000 - $300,000 USD per year

Benefits:

• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

🎯 Team & Company Context

🏢 Company & Design Culture

Industry: Mental Health Care

Company Size: 501-1,000 employees

Founded: 2019

Team Structure:

• Headway's research team is a lean, strategic function that drives business impact through consistent, high-quality insights.
• The team works closely with cross-functional leaders to inform product development, marketing strategy, sales enablement, and customer experience.

Methodology:

• Headway's research methodology is customer-centric, combining qualitative and quantitative approaches to gain a deep understanding of mental health providers and patients.
• The team uses modern tools and techniques to collect, analyze, and share insights, ensuring that every major decision is grounded in deep customer understanding.

Company Website: headway.co

📈 Career & Growth Analysis

Design Career Level: Senior-level role with significant leadership and strategic influence responsibilities.

Reporting Structure: This role reports directly to the Chief Product Officer and works closely with cross-functional leaders to drive company-wide strategy and roadmaps.

Design Impact: The Director of UX Research and Insight will have a significant impact on Headway's product development, marketing strategy, sales enablement, and customer experience, influencing thousands of providers and millions of patients.

Growth Opportunities:

• This role offers the opportunity to build and lead a world-class team of researchers, driving strategic decisions across Headway's business.
• The Director of UX Research and Insight will have the chance to shape the company's research function, ensuring that every major decision is grounded in deep customer understanding.
• As Headway continues to grow, this role presents numerous opportunities for career progression and leadership development.

🌐 Work Environment

Studio Type: Headway's offices in New York City, San Francisco, and Seattle provide collaborative workspaces designed to foster creativity and innovation.

Office Location(s): New York City, San Francisco, and Seattle

Design Workspace Context:

• Headway's offices are equipped with modern tools and technologies to support research and design work.
• The company encourages a flexible work-from-home policy, allowing researchers to balance remote and on-site work as needed.
• Headway's offices are designed to facilitate collaboration and knowledge sharing among team members and across departments.

Work Schedule: Headway offers a flexible work schedule, with core hours from 10:00 AM to 04:00 PM EST, and the option to work remotely.

📄 Application & Portfolio Review Process

Design Interview Process:

• Initial phone or video screen with the hiring manager to discuss the role and assess cultural fit.
• On-site or virtual interview with the hiring manager and cross-functional stakeholders to discuss research methodologies, strategic thinking, and leadership skills.
• Final interview with the Chief Product Officer to assess strategic alignment and cultural fit.

Portfolio Review Tips:

• Highlight examples of driving research initiatives that informed executive decision-making and product strategy.
• Include specific research methodologies used in previous roles, such as user interviews, surveys, usability testing, etc.
• Demonstrate experience with specific research tools and platforms (e.g., UserTesting, Qualtrics, etc.).
• Showcase customer insight artifacts (persona, JTBD, customer journeys, etc.) created and used in previous roles.

Challenge Preparation:

• Prepare for questions related to research methodologies, strategic thinking, and leadership skills.
• Brush up on Headway's mission, values, and research approach.
• Research the company's competitors and industry trends to demonstrate a strong understanding of the market landscape.

ATS Keywords:

• Design Skills: UX Research, Customer Insight, Qualitative Research, Quantitative Research, Market Research, Clinical Research, Research Methodologies, Strategic Thinking, Leadership, Executive Communication
• Tools: UserTesting, Qualtrics, Research Tools, Research Platforms
• Methodologies: User Interviews, Surveys, Usability Testing, Customer Journey Mapping, Persona Development, JTBD Analysis
• Soft Skills: Leadership, Strategic Thinking, Executive Communication, Cross-Functional Collaboration, Team Management
• Industry Terms: Mental Health Care, Healthcare Providers, Patient Experience, Customer-Centric Design, Product Strategy, Roadmap Development

🛠 Tools & Technology Stack

Primary Design Tools:

• UserTesting: A popular remote usability testing platform used for gathering user feedback and insights.
• Qualtrics: A comprehensive experience management platform for creating, distributing, and analyzing surveys and other customer feedback.

Collaboration & Handoff:

• Slack: A team communication platform used for collaboration and knowledge sharing among team members and across departments.
• Google Workspace: A suite of cloud-based productivity tools, including Google Docs, Sheets, and Slides, used for collaboration and document sharing.

Research & Testing:

• Google Forms: A survey creation and data collection tool used for gathering user feedback and insights.
• Google Analytics: A web analytics service used for measuring and analyzing website traffic and user behavior.

👥 Team Culture & Values

Design Values:

• Customer-Centric: Prioritize the needs and perspectives of mental health providers and patients in all decision-making processes.
• Data-Driven: Use data and insights to inform strategic decisions and measure the impact of design and research efforts.
• Collaborative: Foster a culture of knowledge sharing and cross-functional collaboration to drive innovation and growth.
• Adaptable: Embrace change and continuously evolve research methodologies and tools to meet the evolving needs of the business and users.

Collaboration Style:

• Headway's research team works closely with cross-functional leaders to inform product development, marketing strategy, sales enablement, and customer experience.
• The team uses a data-driven approach to gather and analyze insights, ensuring that every major decision is grounded in deep customer understanding.
• Headway fosters a culture of knowledge sharing and collaboration, encouraging team members to learn from one another and contribute to the company's collective expertise.

⚡ Challenges & Growth Opportunities

Design Challenges:

• Scaling Research: As Headway continues to grow, the Director of UX Research and Insight will face the challenge of scaling the research function to keep pace with the company's expansion.
• Cross-Functional Alignment: Balancing the needs and priorities of multiple departments and stakeholders can be challenging, requiring strong communication and collaboration skills.
• Data Silos: Ensuring that research insights are accessible and actionable across the organization can be a significant challenge, requiring a strategic approach to data management and sharing.
• Methodology Evolution: As the mental health landscape evolves, the Director of UX Research and Insight will need to adapt research methodologies to address emerging trends and user needs.

Learning & Development Opportunities:

• Team Leadership: This role offers numerous opportunities for developing and honing leadership skills through team management and mentorship.
• Strategic Thinking: Working closely with cross-functional leaders and executives, the Director of UX Research and Insight will have ample opportunities to refine and develop strategic thinking skills.
• Research Methodologies: As Headway's research function evolves, the Director of UX Research and Insight will have the chance to explore and implement new research methodologies and tools.

💡 Interview Preparation

Design Process Questions:

• Describe your experience leading and managing research teams, including qualitative and quantitative research, UX research, market research, and clinical research, as well as program managers.
• How have you driven research initiatives that informed executive decision-making and product strategy in previous roles?
• Can you walk us through an example of how you translated business questions into actionable research plans and presented impactful insights to stakeholders?

Company Culture Questions:

• How do you ensure that research insights are accessible and actionable across the organization, fostering a culture of knowledge sharing and collaboration?
• Can you describe your experience working with cross-functional leaders and executives to drive strategic decisions and influence product strategy?
• How do you balance the needs and priorities of multiple departments and stakeholders, ensuring that research efforts align with the company's overall mission and goals?

Portfolio Presentation Strategy:

• Prepare a portfolio showcasing your experience leading and managing research teams, driving research initiatives that informed executive decision-making and product strategy, and presenting impactful insights to stakeholders.
• Highlight specific research methodologies, tools, and platforms used in previous roles, and explain how they contributed to your success.
• Demonstrate your ability to translate complex data and insights into clear, actionable recommendations for stakeholders.

📌 Application Steps

To apply for this Director, UX Research & Customer Insight position at Headway:

• Submit your application through the provided link
• Prepare a portfolio showcasing your experience leading and managing research teams, driving research initiatives that informed executive decision-making and product strategy, and presenting impactful insights to stakeholders.
• Tailor your resume to highlight your relevant skills, experiences, and accomplishments in research leadership, strategic thinking, and cross-functional collaboration.
• Research Headway's mission, values, and research approach to demonstrate a strong understanding of the company and its goals.
• Prepare for interviews by practicing your responses to common research and leadership questions, and brushing up on your knowledge of Headway's products, services, and industry trends.