Lead Product Designer

📍 Job Overview

Job Title: Lead Product Designer

Company: b.well Connected Health

Location: Remote (United States)

Job Type: Full-Time

Category: Product Design / UX/UI

Date Posted: 2026-07-28

Experience Level: 7+ Years

Remote Status: Fully Remote

🚀 Role Summary

• Own and elevate the end-to-end user experience across b.well's product ecosystem, focusing on AI, healthcare data, and consumer-grade digital experiences.

• Drive product design vision, translating the company's mission into actionable design principles, patterns, and North Star product experiences.

• Employ a data-informed design approach, leveraging quantitative data and qualitative research to guide all design decisions and measure success.

• Design innovative AI and conversational UX for agentic AI experiences, ensuring clarity, trustworthiness, and accessibility for diverse users.

• Shape the health data experience, making complex health records and clinical information legible and actionable for consumers.

📝 Enhancement Note: This role is specifically for a Lead Product Designer, implying a senior individual contributor with leadership and strategic responsibilities, rather than a people management role. The focus on AI, healthcare data, and consumer-grade experiences within a B2B2C model (serving health plans, providers, employers, and tech companies) is a key differentiator.

📈 Primary Responsibilities

• Define and lead the product design vision for critical product areas, including the bailey™ AI health assistant, the b.well Health AI SDK, and consumer-facing health experiences.

• Translate b.well's core mission – simplifying healthcare, empowering consumer data control, enabling seamless care navigation, and facilitating healthcare shoppability – into tangible design principles, scalable patterns, and aspirational product experiences.

• Collaborate closely with the Chief Product Officer (CPO) and other product leadership to influence roadmap priorities by providing a strong, design-centric perspective.

• Proactively identify and champion potential experience gaps, addressing them before they evolve into significant product debt.

• Utilize both quantitative data (e.g., funnel analysis, A/B test results) and qualitative user research (e.g., usability studies, user interviews) to inform and validate design decisions, rather than merely confirming pre-existing assumptions.

• Define key performance indicators (KPIs) for product areas, such as activation rates, task completion success, data comprehension, and user engagement, and ensure design work is accountable to these metrics.

• Act as a strategic thought partner to product managers and stakeholders, contributing a data-backed viewpoint to prioritization discussions, not just focusing on execution.

• Design measurement frameworks for new features, establishing clear success criteria and collaborating with analytics teams to analyze post-launch performance.

• Conduct structured usability studies, synthesize behavioral and attitudinal data, and translate findings into actionable product recommendations for the entire team.

• Lead the design of agentic AI interactions, defining how users converse with, trust, and act upon AI-generated insights and recommendations through bailey™ and partner-embedded AI assistants.

• Ensure AI recommendations and clinical data are presented clearly, fostering trust and accessibility for users with varying levels of health literacy and technical expertise.

• Establish design standards for AI explainability, confidence signaling, and strategies for graceful failure in sensitive health contexts.

• Design intuitive experiences for longitudinal health records, clinical summaries, lab results, medication histories, and care gaps, making them understandable and actionable for consumers.

• Collaborate with data and engineering teams to effectively surface critical insights from b.well's extensive integrated data sources (350+) without overwhelming users.

• Apply deep empathy for users navigating complex health journeys, chronic conditions, or diverse health literacy levels.

• Manage the end-to-end design process: from user research and journey mapping in the discovery phase, through wireframing and high-fidelity prototyping, to final design delivery and production quality assurance.

• Maintain and evolve a scalable design system that supports white-label customization for diverse enterprise clients across health plans, providers, and technology partners.

• Design across multiple platforms, including native mobile applications (iOS and Android), web interfaces, and embedded SDK components.

• Work closely with frontend engineers to ensure precise implementation of design intent.

• Mentor and develop junior and mid-level designers, establishing craft standards and providing direct, constructive feedback.

• Champion ongoing user research practices and synthesize insights to inform team decisions.

• Facilitate design reviews, critique sessions, and cross-functional alignment workshops to foster collaboration and shared understanding.

• Act as a visible advocate for design thinking principles throughout the organization.

📝 Enhancement Note: The responsibilities highlight a blend of strategic influence, hands-on design execution, and leadership. The emphasis on data-informed decision-making, AI/conversational UX, and health data interaction is significant. The expectation to mentor junior designers positions this as a lead role within the design function.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in design principles, human-computer interaction, or a related field is typically expected. A Bachelor's or Master's degree in Design, HCI, Computer Science, or a related field is often preferred.

Experience: 7+ years of professional product design experience, with a minimum of 2 years in a senior lead or lead capacity, demonstrating progression and leadership within design teams.

Required Skills:

• A comprehensive portfolio showcasing expertise in designing complex, data-rich user experiences for consumer-facing products, with clear documentation of the problem, design process, metrics tracked, and achieved outcomes.

• Proven track record of designing and launching successful consumer products at scale (B2C, high-engagement mobile or web applications) that cater to users with choices and limited tolerance for friction.

• Extensive experience designing AI-powered or conversational interfaces, including chat applications, virtual assistants, or agentic workflows.

• Demonstrated proficiency in employing a data-informed design approach: ability to instrument designs for data collection, analyze user funnels, conduct A/B tests, and leverage insights for iterative design improvements.

• Experience in building, maintaining, and scaling design systems, including component libraries, documentation, and governance frameworks.

• Advanced proficiency in Figma for prototyping, auto-layout, variables, and component library management.

• Exceptional verbal and written communication skills, with the ability to articulate design rationale and research findings effectively to product, engineering, and executive stakeholders.

• Strong understanding of end-to-end design lifecycle, from user research and journey mapping to high-fidelity prototyping and production QA. Preferred Skills:

• Background in B2C consumer products within sectors like fintech, wellness, fitness, navigation, insurance, or financial services, where simplifying complexity is a primary design challenge.

• Experience designing white-label or multi-tenant products where a single design system must accommodate and express multiple distinct brand identities.

• Familiarity with healthcare data standards (e.g., FHIR) and terminology, or a proven ability to rapidly acquire domain expertise in complex industries.

• Experience designing for developer-facing products, such as SDKs, APIs, developer portals, or associated documentation UIs.

• Understanding of health equity, accessibility standards (WCAG), and plain language design principles.

• Prior experience designing products subject to regulatory or compliance requirements (e.g., HIPAA, SOC 2, financial regulations).

• Experience designing user flows for identity verification or privacy consent management.

📝 Enhancement Note: The "Must-Haves" clearly define the core competencies and experience required. The "Strong Differentiators" provide valuable insight into what would make a candidate stand out, particularly domain-specific experience in healthcare, finance, or regulated industries, and experience with multi-tenant/white-label solutions.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate mastery of complex, data-rich UX across consumer-facing products.

• Clearly articulate the problem statement for each project.

• Detail your specific design process, including research methodologies, ideation techniques, and iteration cycles.

• Showcase the metrics you tracked and how they informed your design decisions.

• Present the measurable outcomes and impact of your design solutions.

• Include examples of designing AI-powered or conversational interfaces.

• Highlight contributions to or utilization of design systems.

• Provide examples of high-fidelity prototypes and user flows. Process Documentation:

• Showcase your approach to user research, including methods for synthesizing qualitative and quantitative data.

• Detail how you instrument designs for data collection and analysis (e.g., defining KPIs, tracking funnels, A/B testing).

• Present case studies that illustrate your ability to translate research findings and data insights into actionable design recommendations.

• Demonstrate experience in managing the end-to-end design lifecycle, from discovery to delivery.

• Illustrate your understanding of agile development processes and collaboration with engineering teams.

📝 Enhancement Note: The portfolio requirements are heavily emphasized, particularly the need to demonstrate data-informed decision-making and measurable outcomes. Candidates should prepare case studies that explicitly link design choices to business or user metrics.

💵 Compensation & Benefits

Salary Range: $150,000 - $170,000 per year. This is an estimated range based on the provided information and industry benchmarks for a Lead Product Designer role in the US.

Benefits:

• Stock options: Equity participation in the company's growth.

• Incentive pay: Performance-based bonuses or other variable compensation.

• Health benefits: Comprehensive medical, dental, and vision coverage.

• Other potential benefits include: Paid Time Off (PTO), 401(k) matching, professional development stipends, and remote work support.

Working Hours: The role is listed as full-time, typically implying a standard 40-hour work week. Given the fully remote nature, there may be some flexibility in daily scheduling, but core collaboration hours will likely be expected.

📝 Enhancement Note: The salary range is explicitly stated. The benefits listed are common for Series C-stage tech companies, with stock options and incentive pay being key components of the total compensation package. The estimate for "other potential benefits" is based on standard offerings in the tech industry for fully remote roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology (HealthTech). b.well Connected Health operates at the intersection of digital health, AI, and data interoperability, aiming to revolutionize the consumer healthcare experience. The company leverages AI partnerships with OpenAI, Samsung, and Google, and aligns with CMS standards.

Company Size: The description notes b.well as a Series C-stage company, suggesting a growth phase with likely 100-500 employees. This size typically offers a dynamic environment with opportunities for significant impact, while still maintaining a degree of agility and direct access to leadership.

Founded: While the founding date isn't explicitly stated, being a Series C company indicates it has been operational for several years, establishing market presence and product maturity.

Team Structure:

• The design team likely includes a mix of senior and mid-level designers, potentially with specialists in UX research, interaction design, and visual design.

• This Lead Product Designer role will likely report into a Head of Product Design or VP of Product, working closely with Product Managers, Engineering Leads, and potentially Data Scientists.

• Cross-functional collaboration is expected to be high, involving close partnerships with Product Management, Engineering, Data Science, Marketing, and Executive leadership. Methodology:

• Data Analysis & Insights: Emphasis on using quantitative data (funnels, A/B tests) and qualitative research to drive design decisions and measure success.

• Workflow Planning & Optimization: Designing seamless user journeys and optimizing complex healthcare navigation processes.

• Automation & Efficiency: Leveraging AI and platform capabilities to streamline user interactions and data management.

Company Website: https://www.icanbwell.com/

📝 Enhancement Note: The company's focus on AI, healthcare interoperability, and consumer-centricity, coupled with major tech partnerships, positions it as an innovative player in the HealthTech space. The Series C stage implies a solid foundation with significant growth potential.

📈 Career & Growth Analysis

Operations Career Level: This is a Lead Product Designer role, signifying a senior individual contributor position with significant strategic responsibility and influence. It sits at the senior end of the product design career path, requiring not only exceptional design craft but also leadership in vision-setting, mentorship, and cross-functional collaboration.

Reporting Structure: The Lead Product Designer will likely report to a Director or VP of Product Design/Product Management. They will work closely with Product Managers and Engineering Leads on specific product initiatives.

Operations Impact: The role is critical in shaping the user experience of b.well's core platform, AI assistant (bailey™), and SDK. Success in this role directly impacts user adoption, engagement, satisfaction, and the ability of enterprise clients to successfully deploy and brand b.well's solutions. This design leadership contributes significantly to the company's competitive advantage and market positioning.

Growth Opportunities:

• Design Leadership: Potential to grow into a Design Manager or Director role, overseeing larger teams and broader product areas.

• Specialization: Deepen expertise in AI/Conversational UX, HealthTech design, or Design Systems, becoming a recognized expert in these domains.

• Strategic Influence: Further influence product strategy and roadmap development, taking on more ownership of product vision.

• Mentorship: Continue to mentor and develop junior designers, fostering a strong design culture.

• Cross-functional Advancement: Opportunities to move into Product Management or other strategic roles within the company, leveraging design expertise.

📝 Enhancement Note: The growth trajectory for a Lead Product Designer is typically towards more strategic influence, team leadership, or deep specialization. The emphasis on mentorship suggests an immediate need for someone to elevate the craft within the existing team.

🌐 Work Environment

Office Type: Fully Remote. b.well Connected Health supports a distributed workforce, with its headquarters in Baltimore, MD.

Office Location(s): While remote, the company is headquartered in Baltimore, MD. Support for remote employees may include stipends for home office setup or co-working spaces, depending on company policy.

Workspace Context:

• Collaborative Environment: Expect regular virtual collaboration through video conferencing, chat platforms, and collaborative design tools.

• Operations Tools & Technology: Access to industry-standard design and collaboration software (Figma, Slack, Jira, etc.) will be provided.

• Cross-functional Interaction: Frequent interaction with product managers, engineers, researchers, and executive leadership via virtual channels.

Work Schedule: Full-time, typically 40 hours per week. While remote, core working hours will likely be established to facilitate team collaboration across different time zones within the United States. Flexibility may be offered, but responsiveness during key collaboration times is crucial.

📝 Enhancement Note: The fully remote nature requires strong self-discipline and proactive communication skills. The environment is likely fast-paced and collaborative, typical of a growth-stage tech company.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with a recruiter to assess basic qualifications, cultural fit, and interest in the role and company.

• Portfolio Review & Design Discussion: A deeper dive into your portfolio with a hiring manager or senior designer. Expect to walk through 1-2 complex case studies, explaining your process, rationale, and impact.

• Cross-functional Interviews: Interviews with Product Managers and Engineering Leads to assess collaboration style, technical understanding, and ability to work within a product team.

• Design Challenge/Whiteboarding Session: Potentially a session focused on problem-solving, system thinking, or designing a specific feature, often involving whiteboarding or collaborative design tool exercises.

• Executive/Leadership Interview: A final conversation with a senior leader (e.g., CPO, Head of Design) to discuss strategic thinking, leadership potential, and overall alignment with company vision.

Portfolio Review Tips:

• Curate Strategically: Select 2-3 projects that best showcase your experience with complex, data-rich UX, AI/conversational design, and consumer-facing applications.

• Structure Your Case Studies: For each project, clearly outline:

  • The problem statement and business/user goals.
  • Your specific role and responsibilities.
  • Your design process (research, ideation, iteration, testing).
  • Key design decisions and the rationale behind them.
  • How you incorporated data and user feedback.
  • The metrics used to measure success and the achieved outcomes.
  • Any contributions to design systems or scalable patterns.

• Quantify Impact: Whenever possible, use numbers and data (e.g., "improved task completion by X%", "reduced user errors by Y%", "increased engagement by Z%") to demonstrate the impact of your work.

• Highlight AI/Data: Emphasize projects involving AI, conversational interfaces, or complex data visualization.

• Be Prepared for Deep Dives: Anticipate detailed questions about your decision-making process, trade-offs made, and how you handled challenges.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with b.well's mission, products (bailey™, SDK), and the healthcare technology landscape.

• Practice Problem Solving: Prepare to tackle hypothetical design challenges related to healthcare data simplification, AI interaction, or user engagement.

• Articulate Your Process: Be ready to explain your design thinking process clearly and concisely, even under pressure.

• Consider Constraints: Think about potential constraints like technical limitations, regulatory requirements, or business goals.

• Focus on User Value: Always anchor your solutions in user needs and business objectives.

📝 Enhancement Note: The interview process is structured to evaluate both design craft and strategic thinking. The portfolio is paramount, and candidates must be prepared to articulate their process and impact with data.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for UI design, prototyping, auto-layout, variables, and component library management. Mastery is a requirement.

• Prototyping Tools: Beyond Figma, familiarity with other prototyping tools might be beneficial, but Figma is the stated standard.

• User Research Platforms: Tools like UserTesting.com, Maze, Lookback, Dovetail, or similar for conducting usability studies and synthesizing research.

Analytics & Reporting:

• Web/Mobile Analytics: Experience with tools like Google Analytics, Amplitude, Mixpanel, or similar for tracking user behavior, funnels, and engagement metrics.

• A/B Testing Platforms: Familiarity with tools or methodologies for running controlled experiments (e.g., Optimizely, VWO, or in-house solutions).

• Data Visualization Tools: While not explicitly mentioned, experience with tools like Tableau, Looker, or Power BI can be beneficial for understanding and presenting data insights.

CRM & Automation:

• Project Management: Tools like Jira, Asana, or Trello for managing design tasks and collaborating with engineering.

• Collaboration: Slack for real-time communication, Confluence for documentation.

• Design System Management: Tools or processes for documenting and sharing design system components and guidelines.

📝 Enhancement Note: Figma proficiency is non-negotiable. Experience with analytics platforms and A/B testing is crucial given the emphasis on data-informed design. Understanding of how designs integrate with development workflows (e.g., Jira) is also important.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to simplifying healthcare and empowering consumers. Expect a culture where the impact of work on people's lives is highly valued.

• Design Excellence: A belief that high-quality user experience is a significant competitive advantage. The design team's voice is expected to be heard and respected.

• Data-Informed Decision Making: A culture that values evidence-based design, using data and research to guide strategy and execution.

• Innovation & Collaboration: Encouragement of new ideas, especially around AI and cutting-edge technology, with a strong emphasis on teamwork across departments.

• Consumer-Centricity: A relentless focus on understanding and serving the needs of the end consumer, even within a B2B2C model.

• Efficiency & Action: A drive to move quickly, iterate, and deliver impactful solutions, with a focus on measurable results.

Collaboration Style:

• Cross-functional Integration: Design is integrated early and often with Product Management and Engineering. Expect close collaboration on roadmap planning, feature development, and problem-solving.

• Open Feedback Culture: Encouragement of constructive critique sessions and open feedback loops to improve design quality and team processes.

• Knowledge Sharing: Practices that promote sharing insights from research, design explorations, and best practices across the team and wider organization.

• Proactive Communication: Essential for a remote environment, with an expectation of clear and timely communication regarding progress, challenges, and ideas.

📝 Enhancement Note: The culture appears to be a blend of mission-driven purpose, a strong appreciation for design, data-driven rigor, and collaborative execution, all within a remote-first framework.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Healthcare Complexity: The inherent complexity of healthcare data, terminology, and navigation presents a significant design challenge. Making this accessible and actionable for diverse users requires deep empathy and innovative solutions.

• Designing Trustworthy AI: Building user trust in AI-driven health recommendations and interactions is critical, especially in a sensitive domain like healthcare. This involves careful consideration of explainability, transparency, and error handling.

• Balancing Consumer Needs with Enterprise Requirements: Designing a platform that serves both individual consumers and enterprise clients (health plans, providers) with varying needs, branding requirements (white-label), and technical integrations.

• Rapidly Evolving Technology: Keeping pace with advancements in AI, data interoperability standards (like FHIR), and evolving consumer expectations in digital health.

• Data Overload: Effectively surfacing relevant insights from a vast amount of health data without overwhelming or confusing users.

Learning & Development Opportunities:

• AI/Conversational UX Expertise: Deepen skills in designing cutting-edge AI interactions and conversational interfaces.

• HealthTech Domain Mastery: Become an expert in the nuances of healthcare data, regulations, and user needs within the HealthTech industry.

• Design System Leadership: Contribute to and lead the evolution of a scalable design system supporting multi-brand expression.

• Strategic Product Influence: Develop skills in influencing product strategy and roadmap decisions at a senior level.

• Mentorship & Leadership: Grow leadership capabilities through mentoring junior designers and contributing to design team culture.

• Industry Exposure: Potential to engage with industry conferences or workshops related to HealthTech, AI, or UX design.

📝 Enhancement Note: The challenges are directly tied to the company's mission and industry. The growth opportunities align with advancing expertise in key areas and taking on greater strategic responsibility.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to simplify a highly complex or data-intensive user experience. What was your approach, what challenges did you face, and what were the results?" (Focus on process, data, and impact.)

• "How do you approach designing AI-powered experiences? What are the key considerations for building user trust in AI recommendations, especially in healthcare?" (Discuss AI UX principles, explainability, and ethical considerations.)

• "Walk us through a project where user data significantly changed your design direction. What data did you use, and how did you incorporate it into your process?" (Highlight data-informed decision-making and iterative design.)

• "How would you approach designing a user experience for a longitudinal health record that needs to be understood by both patients and clinicians?" (Assess problem-solving and user empathy for different audiences.)

• "Imagine you need to design a feature for our bailey™ AI assistant. What would be your first steps, and what metrics would you focus on?" (Evaluate strategic thinking and metric definition.) Company & Culture Questions:

• "Why are you interested in b.well Connected Health and our mission to simplify healthcare?" (Demonstrate research and alignment with company values.)

• "How do you see design contributing to b.well's competitive advantage?" (Discuss the strategic role of design.)

• "Describe your experience working in a remote-first environment. How do you ensure effective collaboration and communication?" (Assess remote work readiness and collaboration skills.)

• "How do you mentor or provide feedback to other designers?" (Evaluate leadership and mentorship potential.) Portfolio Presentation Strategy:

• Tell a Story: Frame each case study as a narrative – the challenge, your journey, and the resolution.

• Focus on Impact: Clearly articulate the "so what?" for each project. Quantify results whenever possible using metrics.

• Explain Your 'Why': Be ready to defend your design decisions, explaining the rationale behind key choices and trade-offs.

• Show, Don't Just Tell: Use visuals effectively – mockups, prototypes, user flow diagrams, research synthesis.

• Highlight Data & AI Experience: Explicitly call out projects where you used data to drive decisions or designed AI/conversational interfaces.

• Be Concise: Respect the interviewer's time; focus on the most critical aspects of each project.

📝 Enhancement Note: Prepare specific examples that align with the job description's focus on data, AI, complex UX, and consumer products. Be ready to discuss your role, process, and quantifiable impact in detail.

📌 Application Steps

To apply for this Lead Product Designer position:

• Submit your application through the provided link on the recruitingbypaycor.com portal.

• Customize Your Resume: Tailor your resume to highlight keywords and experiences mentioned in the job description, such as "Product Design," "AI Interaction Design," "Data-Informed Design," "Figma," "Design Systems," and "Healthcare Technology." Quantify achievements with metrics where possible.

• Curate Your Portfolio: Select 2-3 of your strongest projects that best demonstrate your expertise in complex consumer UX, AI/conversational design, and data-driven decision-making. Ensure each project clearly outlines the problem, your process, your role, the metrics tracked, and the outcomes achieved.

• Prepare Your Narrative: Practice articulating your design process, rationale, and the impact of your work for each portfolio case study. Be ready to discuss your experience with AI, data analysis, and user research.

• Research b.well: Familiarize yourself with b.well Connected Health's mission, products (like bailey™), target market, and recent news. Understand their approach to healthcare interoperability and AI.

⚠️ 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.