Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer Company: Waymark Location: US - Remote Job Type: Full-time Category: Product Design / User Experience Date Posted: 2025-07-24T21:41:43 Experience Level: Mid-Senior Level (3-7 years) Remote Status: Fully Remote

🚀 Role Summary

• Design user-centered digital products and experiences that directly impact healthcare outcomes for underserved communities, particularly Medicaid beneficiaries.
• Collaborate closely with product, engineering, and data science teams to translate complex user needs into intuitive and effective solutions.
• Conduct thorough user research, including participatory design methodologies, to deeply understand the challenges faced by community health workers and patients.
• Develop end-to-end user flows, wireframes, and high-fidelity prototypes for a proprietary CRM platform focused on automated patient outreach, appointment scheduling, and care coordination.
• Ensure all designs adhere to strict healthcare compliance standards, including HIPAA and accessibility requirements, while amplifying community wisdom and lived experiences.

📝 Enhancement Note: This role is for a Senior Product Designer, indicating a need for significant experience in end-to-end product design, with a strong emphasis on user research and a passion for mission-driven work within the healthcare sector. The "second designer" aspect suggests a critical role in shaping the design function and potentially mentoring future hires.

📈 Primary Responsibilities

• Lead the design process for Waymark's technology solutions, focusing on enhancing the impact of community-based care programs and reducing manual labor for care teams.
• Conduct qualitative and quantitative user research with diverse stakeholders, including community health workers, pharmacists, therapists, care coordinators, and patients, to identify pain points and opportunities for innovation.
• Design user flows, wireframes, mockups, and interactive prototypes for Waymark's proprietary CRM platform, supporting features like automated patient outreach, appointment scheduling, and care coordination.
• Create user-friendly and customizable interfaces that provide actionable insights to care teams, enabling them to focus on patient goals rather than administrative tasks.
• Design AI-assisted workflows that build trust and complement human-centered care delivery, ensuring technology amplifies, rather than replaces, the human element.
• Partner with the existing designer to evolve and maintain the company's design system, establishing scalable design patterns for community-based care technology.
• Collaborate effectively with cross-functional teams, including product managers, engineers, and data scientists, to implement and iterate on user experience improvements based on feedback.
• Contribute to product strategy discussions, bringing a design perspective to shape the future of community-based care technology and Waymark's overall mission.
• Ensure all designed solutions comply with healthcare regulations such as HIPAA and meet accessibility standards (e.g., WCAG).

📝 Enhancement Note: The responsibilities emphasize a "participatory design" approach, highlighting the importance of co-designing with the community and valuing lived experiences. This is a key differentiator from traditional software design and requires a designer who is comfortable with deep user immersion and advocacy.

🎓 Skills & Qualifications

Education:

• Bachelor's degree in Design, Human-Computer Interaction (HCI), Computer Science, or a related field, or equivalent practical experience.

Experience:

• 3-7 years of professional product design experience, with a strong preference for experience in AI, healthcare technology, or mission-driven organizations.
• Demonstrated experience in designing for complex workflows and solving challenging user problems, particularly in B2B or B2B2C SaaS environments.
• Proven ability to conduct user research, including interviews, surveys, usability testing, and ethnographic studies, to inform design decisions.
• Experience working within regulated environments and understanding healthcare compliance requirements like HIPAA and accessibility standards.
• Track record of successfully launching digital products and iterating based on user feedback and performance data.

Required Skills:

• Human-Centered Design: Deep understanding and application of human-centered design principles and methodologies.
• User Research: Proficiency in planning and executing various user research techniques to uncover user needs and validate design solutions.
• Prototyping & Wireframing: Expertise in using industry-standard design tools (e.g., Figma, Sketch, Adobe XD) for wireframing, prototyping, and creating high-fidelity mockups.
• Cross-Functional Collaboration: Ability to work effectively with product managers, engineers, data scientists, and other stakeholders, fostering strong working relationships.
• Communication & Presentation: Excellent verbal and written communication skills, with the ability to clearly articulate design decisions and present work to diverse audiences, including leadership.
• Healthcare Compliance: Understanding of healthcare regulations (HIPAA) and accessibility standards (e.g., WCAG) relevant to digital product design.
• Startup Acumen: Adaptability and self-starting capabilities, comfortable working in a fast-paced, ambiguous startup environment with a public benefit corporation mission.

Preferred Skills:

• AI/ML Product Design: Experience designing products that incorporate AI or machine learning, particularly in conversational interfaces or AI-assisted workflows.
• Participatory Design / Co-Design: Background in user experience research and participatory design or co-design methodologies, actively involving users in the design process.
• Community Health / Medicaid: Previous experience in community health, Medicaid programs, or care coordination, providing domain-specific context.
• Design Systems: Experience in building, maintaining, or contributing to design systems and component libraries for scalability and consistency.
• Conversational Design: Familiarity with conversational design principles and their application in healthcare contexts.
• Social Determinants of Health: Understanding of social determinants of health and how technology can address them.

📝 Enhancement Note: The "second designer" role implies a need for leadership potential and the ability to influence design direction. Experience with design systems and a strong portfolio showcasing complex problem-solving within regulated or mission-driven sectors will be highly valued.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A strong portfolio showcasing a minimum of 3-5 distinct projects that demonstrate a comprehensive understanding of the end-to-end product design process.
• Projects should highlight your ability to conduct user research, define problems, ideate solutions, prototype, and iterate based on user feedback and business goals.
• Emphasis on projects that solved complex workflow challenges, particularly those involving B2B or B2B2C SaaS products, AI integration, or mission-driven impact.
• Examples of designing for regulated environments or mission-aligned organizations are highly encouraged.
• Visual representation of user flows, wireframes, high-fidelity mockups, and interactive prototypes.

Process Documentation:

• Detailed case studies that clearly articulate the problem statement, your role, the design process followed, key decisions made, and the impact of your solutions.
• Evidence of how user research informed design decisions and how user testing validated those decisions.
• Documentation of collaboration with cross-functional teams (product management, engineering, data science) and how you integrated their feedback.
• Inclusion of any design systems or component libraries you contributed to or utilized.
• Metrics or qualitative feedback demonstrating the success and impact of your designs on user behavior or business outcomes.

📝 Enhancement Note: Given the role's focus on "participatory design" and community impact, portfolios that showcase deep user empathy, ethical design considerations, and measurable improvements in user workflows or outcomes will be particularly impactful. Demonstrating how you translated complex user needs into simple, effective solutions is critical.

💵 Compensation & Benefits

Salary Range:

• The provided salary ranges are based on location within the US, with specific tiers outlined:
  • San Francisco/Bay Area, New York City: $122,500 - $150,000 USD per year
  • Boston, Los Angeles, Seattle, Washington DC: $112,700 - $138,000 USD per year
  • Arlington, Denver, San Diego, Sacramento: $107,800 - $132,000 USD per year
  • Albany, Atlanta, Austin, Baltimore, Central/Southern, Charlotte, Chicago, Dallas/Fort Worth, Detroit, Houston, Las Vegas, Miami, Milwaukee, Philadelphia, Portland, Research Triangle, Salt Lake City, Twin Cities: $98,000 - $120,000 USD per year
  • All other US locations: $95,060 - $116,400 USD per year

Benefits:

• Stock Options: Opportunity for equity participation in the company's growth.
• Work-from-Home Stipend: A dedicated stipend provided in the first year to help establish a home office setup.
• Comprehensive Health Coverage: Medical, Vision, and Dental insurance plans.
• Life Insurance: Basic life insurance coverage.
• Paid Time Off (PTO): 20 vacation days accrued annually, plus 11 paid holidays.
• Parental Leave: 16 weeks of paid leave for birthing parents (after 6 months employment) and 8 weeks of bonding leave for non-birthing parents.
• Retirement Savings: Access to a 401(k) plan with company contributions, subject to a vesting schedule.
• Commuter Benefits: Options to support commute needs.
• Professional Development Stipend: An allocated stipend to support continuous learning and professional growth.

Working Hours:

• While not explicitly stated, a standard full-time role typically involves approximately 40 hours per week. Waymark's mission-driven and startup nature suggests a dynamic environment where flexibility may be present, but a strong commitment to achieving goals is expected.

📝 Enhancement Note: The salary ranges are highly competitive and reflect the company's commitment to attracting top talent for a crucial role. The comprehensive benefits package, including stock options and professional development, further enhances the overall compensation.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology / Health Services Company Size: The job posting mentions being Waymark's "second designer," implying a relatively small, early-stage company, likely with fewer than 50 employees, but growing. This suggests a dynamic and potentially fast-paced environment. Founded: Waymark was founded to address critical gaps in healthcare access for Medicaid beneficiaries, indicating a strong social mission from its inception. The company is focused on building technology and care models to support primary care providers in serving this demographic.

Team Structure:

• Reporting: The Senior Product Designer will report to the Head of Product.
• Collaboration: The role involves close collaboration with product management, engineering, and data science teams, as well as the company's existing product designer.
• Cross-functional Interaction: Expect frequent interaction with community-based care teams (community health workers, care coordinators, etc.) who are the end-users of the platform.

Methodology:

• Participatory Design: A core methodology emphasizing co-creation and learning from the communities served.
• Data-Driven Experimentation: A commitment to using data to inform decisions and assess performance, aligning with the "experiment to improve" core value.
• Community-Centered Approach: Designing solutions that amplify the wisdom of lived experiences and address real-world pain points of underserved populations.

Company Website: waymark.com

📝 Enhancement Note: Waymark operates with a clear mission to improve healthcare for underserved communities. Its core values—bold builders, humble learners, experiment to improve, and act with focused urgency—shape its culture and approach to product development. As the second designer, this role has a significant opportunity to influence the design culture and processes.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, signifying a mid-to-senior level position with significant autonomy and responsibility. It requires not just execution but also strategic input into product direction and design process. Reporting Structure: The role reports directly to the Head of Product, offering visibility and a direct line to leadership in product strategy and development. Operations Impact: The Senior Product Designer will have a direct impact on how care teams operate and how effectively Medicaid patients receive care. By designing intuitive and efficient tools, this role can significantly improve patient outcomes, reduce care team burnout, and contribute to Waymark's mission of expanding healthcare access.

Growth Opportunities:

• Design Leadership: As the second designer, there's a clear path to grow into a design leadership role, potentially managing design initiatives or teams as the company scales.
• Skill Specialization: Opportunity to deepen expertise in specialized areas like healthcare technology, AI-assisted workflows, participatory design, and designing for regulated industries.
• Strategic Influence: Contribute to shaping the product roadmap and the company's overall strategy for community-based care technology.
• Impactful Work: Directly contribute to improving the lives of underserved populations, offering a high degree of job satisfaction and purpose.

📝 Enhancement Note: This role offers a unique opportunity for career growth in a mission-driven startup. The ability to influence product direction and potentially shape the design function makes it attractive for ambitious designers looking to make a significant impact.

🌐 Work Environment

Office Type: Fully Remote. This indicates a distributed workforce, requiring strong asynchronous communication skills and self-discipline. Office Location(s): While the role is remote, the salary bands suggest an awareness of cost of living variations across the US. The company is U.S.-based.

Workspace Context:

• Remote Collaboration: Expect to work primarily through digital collaboration tools, requiring proactive communication and engagement with team members across different locations and time zones.
• Technology Access: As a remote role, access to reliable internet and a suitable home office setup is crucial. The company provides a stipend for this.
• Team Interaction: While remote, the culture emphasizes collaboration and learning, suggesting opportunities for virtual team building and knowledge sharing sessions.

Work Schedule:

• A standard full-time work schedule is implied. Given the startup environment and mission-driven nature, flexibility is likely, but a commitment to meeting project deadlines and delivering results is paramount. Proactive communication regarding availability and working hours will be key.

📝 Enhancement Note: The fully remote nature of this role necessitates strong self-management, proactive communication, and comfort with digital collaboration tools. The company's emphasis on its values suggests a culture that encourages connection and shared purpose despite the distributed workforce.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will likely review applications and portfolios for initial fit.
• Design Challenge/Portfolio Review: Expect a deep dive into your portfolio, potentially involving a presentation of selected case studies and a discussion of your design process, problem-solving approach, and impact. This may include a design challenge.
• Cross-functional Interviews: Interviews with the Head of Product, engineering leads, and potentially other team members to assess collaboration skills, technical understanding, and cultural fit.
• Behavioral and Values-Based Interviews: Questions designed to assess alignment with Waymark's core values (bold builders, humble learners, experiment to improve, focused urgency) and commitment to the mission.

Portfolio Review Tips:

• Curate Effectively: Select 2-3 of your strongest projects that best showcase your skills relevant to this role: human-centered design, complex workflows, healthcare context, and mission-driven impact.
• Tell a Story: For each project, clearly articulate the problem, your role and responsibilities, the process you followed (research, ideation, prototyping, testing), key decisions, and the outcomes/impact. Quantify results where possible.
• Showcase Process: Don't just show final screens; illustrate your thinking, iterations, and how you navigated challenges. Include wireframes, user flows, research insights, and testing results.
• Highlight Collaboration: Mention how you collaborated with cross-functional partners (PMs, engineers) and incorporated their feedback.
• Address Mission Alignment: Be prepared to discuss why Waymark's mission resonates with you and how your design philosophy aligns with their values.

Challenge Preparation:

• If a design challenge is provided, focus on understanding the problem deeply, clearly defining your approach, and communicating your rationale at each step.
• Practice articulating your thought process and design decisions concisely.
• Be prepared to discuss trade-offs and justify your design choices, considering constraints like healthcare compliance and user needs.
• If presenting, ensure your presentation is clear, well-structured, and engaging.

📝 Enhancement Note: The interview process will likely be rigorous, focusing heavily on your design process, problem-solving abilities, and alignment with Waymark's mission and values. A well-prepared portfolio presentation is crucial for showcasing your capabilities and making a strong impression.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable, as it's industry-standard and mentioned as a proficiency requirement), Sketch, Adobe Creative Suite (Illustrator, Photoshop).
• Collaboration & Project Management: Tools like Jira, Asana, Trello, Slack, Google Workspace (Docs, Sheets, Slides).
• User Research Platforms: Tools for conducting remote interviews, surveys, and usability testing (e.g., UserTesting.com, Lookback, Maze, SurveyMonkey).

Analytics & Reporting:

• Analytics Platforms: Google Analytics, Mixpanel, Amplitude (for understanding user behavior and product performance).
• Data Visualization Tools: Tableau, Looker, or similar for creating dashboards and reports (especially if collaborating with data scientists).

CRM & Automation:

• CRM Platform: Waymark has a proprietary CRM platform that the designer will be working on; understanding core CRM functionalities is beneficial.
• Integration Tools: Knowledge of how different systems connect and share data might be helpful, though not explicitly stated as a requirement.

📝 Enhancement Note: Proficiency in Figma is a strong indicator of the expected design toolset. Familiarity with the broader ecosystem of collaboration, research, and analytics tools used in a tech startup environment will be advantageous.

👥 Team Culture & Values

Operations Values:

• Bold Builders: Encouraging innovation and taking initiative to solve complex problems in healthcare delivery.
• Humble Learners: Fostering an environment where seeking feedback, learning from others, and challenging assumptions are valued.
• Experiment to Improve: A data-driven approach to iterating on products and processes, embracing a culture of continuous improvement and learning from results.
• Act with Focused Urgency: A commitment to the mission drives the team to work efficiently and effectively towards achieving significant impact for the communities served.

Collaboration Style:

• Cross-functional Integration: Strong emphasis on working collaboratively with product, engineering, and data science to ensure holistic product development.
• Community Partnership: A unique focus on designing with and learning from the communities served, integrating their feedback and lived experiences directly into the product.
• Open Feedback Culture: Encouraging constructive feedback and open dialogue to drive innovation and improve user experiences.

📝 Enhancement Note: Waymark's values are central to its identity and operations. Candidates should be prepared to demonstrate how they embody these values in their work, particularly the commitment to learning, experimentation, and building solutions for underserved communities.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Underserved Populations: Addressing the unique needs and constraints of Medicaid beneficiaries, who may have diverse technological literacy, access to resources, and cultural backgrounds.
• Balancing Mission with Technical Constraints: Integrating complex healthcare regulations (HIPAA) and ensuring accessibility while creating user-friendly and effective tools.
• Startup Ambiguity: Navigating a fast-paced, evolving startup environment where priorities can shift, requiring adaptability and resilience.
• AI Integration: Designing AI-assisted workflows that are trustworthy, ethical, and genuinely enhance human-centered care without replacing critical human touchpoints.

Learning & Development Opportunities:

• Specialized Domain Knowledge: Gaining deep expertise in community health, Medicaid programs, and social determinants of health.
• AI Product Design: Enhancing skills in designing and implementing AI-powered features, particularly in healthcare.
• Design System Development: Contributing to and potentially leading the growth of a design system for a growing tech company.
• Strategic Impact: Playing a key role in shaping the product and company strategy from an early stage.

📝 Enhancement Note: This role presents a significant opportunity to tackle complex, meaningful challenges in healthcare technology. The growth opportunities are substantial for a designer eager to make a tangible impact and develop specialized skills in a high-growth sector.

💡 Interview Preparation

Strategy Questions:

• Operations Strategy: "How would you approach designing a system to improve patient adherence to medication for individuals with chronic conditions, considering potential barriers like transportation or health literacy?" (Focus on research, user journey mapping, and iterative design).
• Collaboration & Stakeholder Management: "Describe a time you had to balance conflicting feedback from different stakeholders (e.g., engineering, product, users). How did you navigate this and reach a decision?" (Highlight communication, negotiation, and user advocacy).
• Problem-Solving & Process: "Walk us through a complex workflow challenge you've solved through design. What was the problem, your process, and the measurable impact of your solution?" (Prepare a detailed case study from your portfolio).

Company & Culture Questions:

• Company Operations Culture: "What interests you most about Waymark's mission, and how do you see your design philosophy aligning with our core values of bold building and humble learning?" (Research Waymark's mission, values, and recent news).
• Operations Team Dynamics: "How do you prefer to collaborate with product managers and engineers? What do you believe makes for a successful cross-functional design partnership?" (Discuss your ideal collaborative environment and communication strategies).
• Operations Impact Measurement: "How do you measure the success of your designs? What key metrics would you track for a platform aimed at improving care coordination for Medicaid patients?" (Focus on user satisfaction, task completion rates, efficiency gains, and patient outcome improvements).

Portfolio Presentation Strategy:

• Storytelling: Structure your portfolio presentation as a narrative. Begin with the problem, introduce the users, detail your design process and key decisions, showcase the solution, and conclude with the impact and learnings.
• Visual Clarity: Use high-quality visuals for mockups and prototypes. Ensure user flows and wireframes are easy to follow.
• Interactive Elements: If possible, include interactive elements or a live demo of a prototype to engage the interviewers.
• Conciseness: Practice presenting your projects within the allotted time, focusing on the most critical aspects and your thought process. Be prepared for follow-up questions.
• Quantify Impact: Whenever possible, present metrics that demonstrate the success of your designs (e.g., increased engagement, reduced error rates, improved efficiency).

📝 Enhancement Note: Prepare to articulate your design process with clarity and confidence, linking your decisions directly to user needs and business objectives. Be ready to discuss your experience with AI, healthcare, and mission-driven work, and how you embody Waymark's core values.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided Greenhouse link.
• Portfolio Preparation: Curate a compelling portfolio that highlights 2-3 projects demonstrating your human-centered design process, problem-solving skills for complex workflows, and experience with mission-driven or regulated industries. Ensure case studies clearly articulate the problem, your role, process, and impact.
• Resume Optimization: Tailor your resume to emphasize your 3-7 years of product design experience, specific skills in user research, prototyping (especially Figma), collaboration, and any relevant healthcare or AI experience. Quantify achievements where possible.
• Interview Preparation: Practice articulating your design process and portfolio projects using the STAR method (Situation, Task, Action, Result). Prepare to discuss your understanding of Waymark's mission and values and how you contribute to them.
• Company Research: Thoroughly research Waymark's mission, values, and the healthcare landscape for Medicaid beneficiaries. Understand their approach to community-based care and technology.

⚠️ 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.