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: April 24, 2026

Experience Level: 5-10 Years

Remote Status: Fully Remote

🚀 Role Summary

• Lead the end-to-end user experience strategy and execution across b.well's innovative AI-driven healthcare platform and SDKs.

• Drive data-informed design decisions, leveraging quantitative metrics and qualitative research to shape product direction and validate user engagement.

• Spearhead the design of complex AI and conversational UX interactions, focusing on clarity, trust, and actionable insights for consumers and developers.

• Champion a user-centric approach to designing with sensitive health data, making it accessible, understandable, and empowering for diverse user populations.

• Mentor and grow a team of designers, establishing craft standards and fostering a culture of design excellence and continuous improvement.

📝 Enhancement Note: This role is positioned as a Lead Product Designer, implying a significant level of autonomy, strategic influence, and team leadership. The emphasis on AI, healthcare data, and consumer-grade experiences suggests a need for a designer who can translate complex technical and medical information into intuitive, empowering user journeys. The "not a pixel-pusher" comment highlights the expectation for strategic thinking and business acumen alongside design execution.

📈 Primary Responsibilities

• Own and evolve the product design vision and strategy for key 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 promoting healthcare shoppability – into tangible design principles, patterns, and aspirational product experiences.

• Act as a strategic design partner to the Chief Product Officer (CPO) and product leadership, influencing roadmap prioritization through a user experience lens and identifying potential experience gaps proactively.

• Utilize a robust framework for data-informed design, integrating quantitative data analysis (funnel analysis, A/B testing) and qualitative user research (usability studies, behavioral signal synthesis) to drive design decisions and measure success.

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

• Design intuitive and trustworthy AI interaction models for agentic AI experiences, focusing on how users converse with, trust, and act upon AI-generated recommendations and health actions.

• Establish clear standards for AI explainability, confidence signaling, and graceful failure states within the sensitive context of healthcare.

• Create experiences that make longitudinal health records, clinical summaries, lab results, and medication histories legible and actionable for everyday consumers with varying health literacy levels.

• Collaborate closely with data and engineering teams to effectively surface critical health information from b.well's extensive data integrations without overwhelming users.

• Lead the full design lifecycle from discovery and definition through high-fidelity prototyping and delivery, ensuring design intent is accurately translated by frontend engineers across mobile (iOS, Android), web, and embedded SDK components.

• Maintain and advance a scalable design system that accommodates white-label customization for enterprise clients, ensuring brand consistency and flexibility.

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

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

• Serve as a visible advocate for design thinking and user-centric methodologies across the entire organization.

📝 Enhancement Note: The responsibilities clearly delineate a senior-level role requiring strategic thinking, data literacy, and leadership. The emphasis on AI and health data design indicates a need for specialized UX skills. The mention of a design system for white-labeling highlights the complexity of enterprise solutions and the need for scalable design.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's or Master's degree in Design, Human-Computer Interaction (HCI), Computer Science, or a related field is often preferred for senior design roles and can be beneficial.

Experience: 7+ years of professional product design experience, with a minimum of 2 years in a lead or senior lead capacity demonstrating strategic ownership and team mentorship.

Required Skills:

• Proven mastery of complex, data-rich User Experience (UX) design across consumer-facing products, clearly articulated through a compelling portfolio.

• Demonstrated success in designing for large-scale consumer products (B2C, high-engagement mobile or web applications) where user choice and minimal friction are critical.

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

• Strong proficiency in using quantitative data (e.g., funnel analysis, A/B testing results) and qualitative research to inform and validate design decisions.

• Experience building, maintaining, and governing scalable design systems, including component libraries and documentation.

• Expert-level proficiency in Figma, including advanced features like prototyping, auto-layout, variables, and component library management.

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 requiring a single design system to support diverse brand expressions.

• Familiarity with health data concepts (e.g., FHIR, clinical terminology) or a proven ability to quickly master domain-heavy industries.

• Experience designing developer-facing products such as Software Development Kits (SDKs), Application Programming Interfaces (APIs), or developer portals.

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

• 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 a senior-level designer with a strong focus on data-driven decision-making and AI/conversational UX. The "Strong Differentiators" point towards candidates with specific industry experience that would accelerate their impact within b.well's domain. The emphasis on Figma and design systems is crucial for this role.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end design process for complex, data-rich UX challenges, emphasizing problem definition, user research methodologies, ideation, interaction design, and final execution.

• Include detailed case studies demonstrating how quantitative data and qualitative research directly informed and validated design decisions.

• Highlight specific examples of designing AI-powered or conversational interfaces, detailing interaction models, conversational flows, and user trust mechanisms.

• Present work on scalable design systems, illustrating component architecture, documentation, governance, and application in multi-brand or white-label contexts.

• Articulate the impact of your design work through clear metrics and outcomes, demonstrating accountability for user activation, task completion, comprehension, or engagement.

Process Documentation:

• Demonstrate a structured approach to user research, including planning, execution of usability studies, synthesis of findings, and translation into actionable product recommendations.

• Illustrate a methodical approach to defining and tracking design success metrics, showing how you instrument designs and collaborate with analytics teams.

• Document your process for contributing to or maintaining design systems, including interaction with engineering for implementation and governance.

• Provide examples of how you collaborate with product managers and engineers throughout the design and development lifecycle, ensuring design intent is realized.

📝 Enhancement Note: The portfolio requirements are tailored to a lead role, emphasizing strategic impact, data-driven validation, and system-level thinking. The focus on AI, health data, and design systems aligns with the core responsibilities. Applicants should prepare to discuss metrics and ROI.

💵 Compensation & Benefits

Salary Range: $150,000 - $170,000 per year.

Benefits:

• Stock options: Potential for equity ownership in a growing Series C company.

• Incentive pay: Performance-based bonuses or incentive compensation.

• Health benefits: Comprehensive health insurance coverage.

• Other benefits as part of a competitive total rewards package.

Working Hours: 40 hours per week, full-time. The role is fully remote, offering flexibility in work schedule within reasonable operational hours, though specific team collaboration times will be expected.

📝 Enhancement Note: The salary range is explicitly provided. The benefits list is extracted from the AI data and the description. The working hours are inferred from the "full time" designation and standard industry practice. The remote nature implies flexibility, but active collaboration will require adherence to some schedule.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology, focused on healthcare interoperability and AI-driven consumer health experiences. The company operates at the intersection of health tech, AI, and consumer digital products, aiming to simplify complex healthcare journeys.

Company Size: Series C-stage, indicating a growth-oriented environment with established processes but still retaining a degree of agility. The company is likely between 50-250 employees, transitioning from startup to scale-up.

Founded: Founded to address the fragmentation in healthcare, aiming to make health data accessible and actionable for consumers. This mission drives innovation and a user-centric approach.

Team Structure:

• The Product Design team likely includes a mix of junior, mid-level, and senior designers, with this role acting as a Lead.

• Designers will report into Product or Design leadership, potentially a CPO or VP of Product/Design.

• Close collaboration is expected with Product Managers, Engineers (frontend, backend, AI/ML), Data Scientists, and Researchers.

Methodology:

• Data-Informed Design: Decisions are backed by quantitative metrics and qualitative user research.

• Agile Development: Iterative product development cycles are standard.

• User-Centricity: A strong emphasis on understanding and addressing consumer needs in healthcare.

• AI-First Approach: Leveraging AI to create novel and improved health experiences.

• Design System Utilization: Employing a scalable design system for efficiency and consistency, especially for white-label solutions.

Company Website: https://icanbwell.com/

📝 Enhancement Note: The company context is derived from the "About b.well Connected Health" section and the funding stage. The emphasis on mission, advanced technology partnerships, and design's strategic role informs the culture and methodology.

📈 Career & Growth Analysis

Operations Career Level: This role is a "Lead Product Designer," signifying a senior individual contributor with leadership responsibilities. It's a pivotal role for designers aiming to influence product strategy, mentor others, and drive design vision within a specialized domain like health tech and AI.

Reporting Structure: The Lead Product Designer will likely report to a Director of Product Design, VP of Product, or the Chief Product Officer (CPO). They will collaborate closely with Product Managers and Engineering leads on specific product initiatives.

Operations Impact: The Lead Product Designer's impact is significant, directly shaping the user experience of products that aim to revolutionize healthcare access and data management. Their work influences consumer engagement, developer adoption of the SDK, and the success of enterprise clients deploying b.well's solutions. They are instrumental in turning complex health data and AI capabilities into simple, empowering user journeys, which directly impacts user trust, adoption, and ultimately, business growth.

Growth Opportunities:

• Leadership Development: Opportunity to formally lead and mentor designers, honing management and strategic leadership skills.

• Domain Specialization: Deepen expertise in healthcare interoperability, AI/conversational UX, and data-rich consumer applications.

• Strategic Influence: Grow influence on product roadmap, strategy, and company-wide design culture.

• Technical Acumen: Develop a deeper understanding of AI architectures, health data standards (like FHIR), and SDK design.

• Cross-Functional Acumen: Enhance skills in collaborating with C-suite executives, product, and engineering leadership on high-stakes initiatives.

• Potential for Group Lead/Director Role: Success in this role can pave the way for more senior leadership positions within the design organization as the company scales.

📝 Enhancement Note: The growth analysis focuses on the "Lead" aspect of the role, highlighting progression beyond individual contribution into strategic and leadership domains, particularly within the specialized context of health tech and AI.

🌐 Work Environment

Office Type: Fully Remote. This means the company operates with a distributed workforce, with no central physical office required for this role.

Office Location(s): While the company is headquartered in Baltimore, MD, this role is open to candidates located anywhere within the United States, provided they can work effectively remotely.

Workspace Context:

• Collaborative Environment: Expect a highly collaborative remote environment, utilizing digital tools for communication, design collaboration (Figma), and project management.

• Operations Tools & Technology: Access to industry-standard design tools (Figma), collaboration platforms (Slack, Zoom), project management software (likely Jira or similar), and potentially analytics dashboards.

• Team Interaction: Regular virtual meetings, design critiques, brainstorming sessions, and 1:1s with team members and stakeholders to foster connection and alignment.

Work Schedule: Standard 40-hour work week. While fully remote, candidates should be prepared to align with core business hours for team collaboration and stakeholder meetings, likely within US time zones. Flexibility may be possible, but consistent availability for team interaction is key.

📝 Enhancement Note: The description explicitly states "full time and open to fully remote work." The company headquarters in Baltimore, MD, is mentioned, but the remote nature for this role implies it's not tied to a specific office location beyond the country.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review your application and portfolio for alignment with the core requirements.

• Portfolio Review & Design Challenge: Expect a deep dive into your portfolio, focusing on your process, problem-solving approach, and impact. A design challenge, potentially involving a case study or a prompt related to AI/health data, is likely.

• Cross-Functional Interviews: Interviews with Product Managers, Engineering leads, and potentially other designers to assess collaboration skills, technical understanding, and cultural fit.

• Executive Interview: A final interview with senior leadership (e.g., CPO, CEO) to evaluate strategic thinking, vision, and alignment with company mission.

Portfolio Review Tips:

• Storytelling: Structure your case studies to tell a compelling story: the problem, your approach, your role, the insights gained, the solutions designed, and the measurable outcomes.

• Process Emphasis: Clearly articulate your design process, highlighting how you used research, data, and collaboration to arrive at your solutions.

• Metrics & Impact: Quantify your impact wherever possible. Discuss metrics you influenced (activation, engagement, task completion) and demonstrate ROI.

• AI & Data Focus: Showcase specific work related to AI interactions, conversational UX, or designing with complex data sets, especially if you have healthcare experience.

• Figma Proficiency: Be prepared to discuss your Figma workflow, including design system contributions, auto-layout usage, and prototyping techniques.

• Tailor to b.well: Research b.well's mission and products. Highlight relevant experience that aligns with their focus on simplifying healthcare, AI, and data unification.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with healthcare data challenges, AI assistant interactions, and user needs in managing health information.

• Focus on Strategy: For any design challenge, think beyond just the UI. Consider the business goals, user needs, technical constraints, and scalability.

• Data-Driven Rationale: Be ready to explain the "why" behind your design decisions, referencing data or user research principles.

• Communication: Practice articulating your thought process clearly and concisely, as if presenting to a mixed audience of designers, product managers, and engineers.

📝 Enhancement Note: This section synthesizes common interview practices for lead design roles, combined with specific requirements mentioned in the job description (portfolio, Figma, AI/data focus, mentorship). The "What Success Looks Like" section provides excellent clues for interview preparation.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for all aspects of design, including wireframing, high-fidelity prototyping, design system management, auto-layout, and variables.

• Prototyping Tools (within Figma): Advanced prototyping capabilities for demonstrating complex interactions and user flows.

• Design Systems: Experience with creating, maintaining, and scaling design systems is critical, likely involving component libraries and documentation standards.

Analytics & Reporting:

• Analytics Platforms (e.g., Amplitude, Mixpanel, Google Analytics): While not directly a designer's tool, understanding how to instrument designs for analytics and interpret funnel data is crucial.

• Data Visualization Tools (e.g., Tableau, Looker): Familiarity with how data is visualized and presented can aid in designing effective dashboards and reports.

CRM & Automation:

• Project Management Tools (e.g., Jira, Asana, Trello): For managing design tasks, sprints, and collaborating with engineering teams.

• Collaboration Platforms (e.g., Slack, Microsoft Teams): For daily communication and team interaction.

Specialized Healthcare/AI Tools:

• FHIR Standards: Understanding or familiarity with Fast Healthcare Interoperability Resources (FHIR) is a strong differentiator, indicating an ability to work with health data standards.

• AI/ML Platforms: While not directly designing the models, understanding the output and interaction patterns of AI/ML systems will be beneficial.

📝 Enhancement Note: This section focuses on the tools explicitly mentioned (Figma) and inferred based on the role's responsibilities (design systems, analytics, collaboration). The mention of FHIR as a differentiator is key.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to simplifying healthcare and empowering consumers, fostering a sense of purpose in the work.

• User-Centricity: Placing the needs and experiences of consumers at the forefront of all product development decisions.

• Data-Driven: Valuing evidence-based decision-making, using both quantitative and qualitative data to guide strategy and execution.

• Innovation: Encouraging creative problem-solving and embracing new technologies, particularly AI, to transform healthcare.

• Collaboration: Fostering a team environment where cross-functional partnerships are essential for success.

• Quality & Craftsmanship: Holding high standards for design quality, user experience, and attention to detail.

Collaboration Style:

• Cross-functional Integration: Designers are expected to work seamlessly with Product Managers and Engineers, acting as true partners rather than order-takers.

• Open Communication: Encouraging direct, honest feedback through design reviews and critique sessions.

• Knowledge Sharing: Promoting the sharing of insights from research, data analysis, and design explorations across teams.

• Iterative Mindset: Embracing an agile approach where designs are continuously refined based on feedback and performance data.

📝 Enhancement Note: These values are inferred from the company's mission, the emphasis on data-informed design, and the collaborative nature of product development in a tech company. The "Why b.well" section is a rich source for these cultural insights.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Healthcare Complexity: The inherent difficulty in making complex medical information and healthcare navigation intuitive and accessible for all users.

• Designing for Trust in AI: Building user trust and confidence in AI-driven health recommendations and actions, especially in a sensitive domain like healthcare.

• Balancing Consumer & Enterprise Needs: Designing a flexible system that serves individual consumers while also meeting the white-label customization and integration needs of enterprise clients.

• Navigating Health Data Privacy & Security: Designing experiences that are compliant with regulations like HIPAA while also being user-friendly.

• Remote Collaboration Dynamics: Maintaining strong team cohesion, communication, and design quality in a fully remote setting.

Learning & Development Opportunities:

• AI Interaction Design Expertise: Becoming a leader in designing advanced AI and conversational user experiences within a regulated industry.

• Health Tech Domain Mastery: Deepening knowledge of healthcare interoperability standards (FHIR), clinical data, and patient journeys.

• Design System Leadership: Gaining experience in scaling and governing robust design systems for diverse applications and brands.

• Strategic Product Influence: Developing skills in shaping product roadmaps and influencing executive-level decisions.

• Mentorship & Team Building: Honing leadership skills through mentoring junior designers and contributing to team growth.

📝 Enhancement Note: Challenges are derived from the core complexities of the role and industry. Growth opportunities are framed around deepening expertise and expanding influence, aligning with the "Lead" position.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing an AI health assistant that needs to build trust with users who are dealing with chronic conditions?" (Focus on AI explainability, graceful failure, user control).

• "Describe your process for translating complex health data (e.g., lab results, medication history) into an actionable and understandable format for a consumer." (Focus on data visualization, plain language, user research).

• "How would you ensure our design system effectively supports white-label customization for enterprise clients across different health plans and providers?" (Focus on component flexibility, theming, governance).

• "Imagine we're seeing low activation rates for a new feature. How would you use data and research to diagnose the problem and propose design solutions?" (Focus on funnel analysis, A/B testing, usability studies).

Company & Culture Questions:

• "Why are you interested in b.well's mission to simplify healthcare?" (Prepare to discuss personal motivations and alignment with the company's purpose).

• "How do you see design contributing to b.well's competitive advantage?" (Focus on user experience as a moat, innovation, and brand differentiation).

• "Describe your experience mentoring junior designers. What is your approach to giving feedback?" (Prepare examples of mentorship and your feedback philosophy).

• "How do you collaborate with product managers and engineers to ensure design quality and successful implementation?" (Highlight your partnership approach and communication strategies).

Portfolio Presentation Strategy:

• Narrative Arc: Structure each case study as a story with a clear beginning (problem/opportunity), middle (your process, challenges, solutions), and end (outcomes, lessons learned).

• Highlight Your Role: Be explicit about your contributions, especially if it was a team project. Use "I" when describing your actions and "we" for team efforts.

• Visual Clarity: Use high-quality visuals (mockups, prototypes, user flows) to illustrate your work. Ensure they are easy to understand.

• Data & Metrics: Dedicate a section to discussing the metrics you influenced and the results achieved. This is critical for a data-informed role.

• AI & Data Examples: Prioritize showcasing work that demonstrates your ability to handle complex data and design AI interactions.

• Conciseness: Be mindful of time. Focus on the most impactful aspects of your work and be prepared to answer deeper questions.

📝 Enhancement Note: These questions are tailored to the specific requirements of the Lead Product Designer role at b.well, emphasizing AI, health data, design systems, and data-driven decision-making. The portfolio presentation strategy focuses on actionable advice for showcasing relevant experience.

📌 Application Steps

To apply for this Lead Product Designer position:

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

• Curate Your Portfolio: Select 2-3 of your most relevant case studies that demonstrate end-to-end complex UX design, ideally with examples of AI/conversational interfaces, data-rich applications, or design systems. Ensure each case study clearly articulates the problem, your process, your role, the outcomes, and any metrics tracked.

• Optimize Your Resume: Tailor your resume to highlight your 7+ years of experience, specific experience in lead roles, proficiency in Figma, and any background in AI, healthcare, or complex B2C products. Use keywords from the job description.

• Prepare Your Narrative: Practice walking through your portfolio, focusing on your problem-solving approach, design rationale, and how you leverage data and research. Be ready to discuss your leadership style and mentorship approach.

• Research b.well: Understand their mission, products (bailey™, SDK), partnerships (OpenAI, Samsung), and their vision for simplifying healthcare. Prepare to articulate why you are a strong fit for their specific goals and culture.

⚠️ 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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