Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Waymark

Location: US - Remote (United States)

Job Type: Full-Time

Category: Product Design / UX/UI

Date Posted: June 10, 2026

Experience Level: Mid-Senior Level (3-5 years)

Remote Status: Fully Remote

🚀 Role Summary

• Drive end-to-end product design for a proprietary CRM platform focused on improving healthcare outcomes for underserved Medicaid populations.

• Lead community-centered design initiatives, conducting user research with care teams and patients to address complex workflow challenges and eliminate manual workarounds.

• Develop user-friendly and customizable interfaces that provide actionable insights, enabling care teams to prioritize patient care.

• Collaborate closely with product management, engineering, and data science to implement and iterate on user experiences, with a focus on AI-assisted workflows and healthcare compliance.

• Contribute to the evolution of the design system and product strategy, embodying the company's mission-driven values and a commitment to inclusive design.

📝 Enhancement Note: While the title is "Senior Product Designer," the description emphasizes that this is the second designer on the team, reporting to the Head of Product. This suggests a significant opportunity for influence and ownership, with the potential to shape the design function and its processes. The role requires not just execution but also strategic input and leadership in establishing design patterns for community-based care technology.

📈 Primary Responsibilities

• Conduct in-depth user research with community health workers, pharmacists, therapists, care coordinators, and patients to deeply understand pain points and identify opportunities for innovative solutions.

• Design user flows, wireframes, and high-fidelity mockups for a proprietary CRM platform, focusing on automated patient outreach, appointment scheduling, and care coordination functionalities.

• Create intuitive and customizable interfaces that surface critical, actionable insights for care teams, thereby reducing administrative burden and allowing for greater focus on patient needs.

• Develop and refine AI-assisted workflows that are trustworthy, collaborative, and augment human-centered care delivery.

• Ensure all design outputs adhere to stringent healthcare compliance standards, including HIPAA regulations and accessibility requirements (e.g., WCAG).

• Collaborate effectively with cross-functional teams, including engineers, product managers, and data scientists, to translate design concepts into implemented features and iterate based on user feedback.

• Partner with the existing Product Designer to evolve and maintain the company's design system, establishing robust patterns for community-based care technology.

• Actively participate in product strategy discussions, contributing a design perspective informed by user insights and the company's core values.

• Champion a participatory design approach, co-creating solutions with the communities Waymark serves, celebrating lived experiences, and designing for inclusivity.

📝 Enhancement Note: The emphasis on "participatory design" and "community-centered design" is a critical differentiator for this role. Applicants should be prepared to demonstrate experience in genuinely co-creating solutions with end-users, rather than simply designing for them in a traditional sense. This implies a need for strong empathy, active listening, and a willingness to adapt designs based on community wisdom.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong understanding of design principles and user-centered methodologies is expected, often gained through a Bachelor's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience.

Experience: 3-5 years of professional product design experience, with a preference for candidates who have experience in AI, healthcare technology, or mission-driven organizations.

Required Skills:

• Demonstrated human-centered design process, evidenced by a strong portfolio showcasing your approach to solving complex workflow challenges.

• Proficiency in industry-standard design and prototyping tools such as Figma, Sketch, Adobe XD, or similar.

• Proven experience conducting user research to effectively identify problems and user testing to validate the efficacy of proposed solutions.

• Understanding of healthcare compliance requirements, including HIPAA, and the ability to design within regulated environments.

• Strong communication and presentation skills, with experience managing cross-functional stakeholders and presenting design work to leadership.

• Ability to design end-to-end user experiences, from conceptualization to implementation.

• Experience with user flows, wireframing, and high-fidelity interface design. Preferred Skills:

• Previous experience working within community health, Medicaid programs, or care coordination settings.

• Background in user experience research, with a strong understanding of participatory design or co-design methodologies.

• Familiarity with community health worker programs and an understanding of social determinants of health.

• Experience with conversational design principles and considerations for AI/ML product design in healthcare contexts.

• Experience in developing and maintaining design systems and component libraries.

📝 Enhancement Note: The "3-5 years" experience level is explicitly stated. Given the "Senior" title and the responsibility of being the second designer, candidates at the higher end of this range (4-5 years) with demonstrable leadership in design projects and a strong portfolio will likely be more competitive. The mention of "mission-driven organizations" and "public benefit corporation mission" suggests that candidates passionate about social impact will be highly valued.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a comprehensive human-centered design process, detailing your approach from initial research and problem definition through to solution design and iteration.

• Include case studies that clearly articulate complex workflow challenges and how your designs effectively addressed them, demonstrating tangible improvements.

• Present examples of user research methodologies employed, including how insights were gathered and translated into design decisions.

• Demonstrate proficiency in relevant design tools (e.g., Figma) through examples of wireframes, user flows, prototypes, and high-fidelity mockups.

• Highlight experience designing for regulated environments, such as healthcare, with an understanding of compliance implications (e.g., HIPAA).

• Provide evidence of collaboration with cross-functional teams and how you managed stakeholder feedback. Process Documentation:

• Detail your approach to user research, including methods for participant recruitment, data collection, and synthesis of findings for actionable insights.

• Illustrate your wireframing and prototyping process, showing how you iterate on concepts to arrive at optimal user flows and interface designs.

• Explain your methodology for ensuring designs meet accessibility standards and healthcare compliance requirements.

• Showcase how you contribute to or maintain design systems, including component creation, pattern definition, and documentation.

📝 Enhancement Note: The portfolio is critical for this role. It should not only showcase design output but also the thinking and process behind it. Case studies demonstrating impact on workflows, particularly in complex or regulated environments, will be highly valued. Given the emphasis on community and participatory design, examples of how users were involved in the design process will be a significant plus.

💵 Compensation & Benefits

Salary Range: The hiring range for this position varies significantly by US location, reflecting regional cost of living and market rates.

• Highest Range (San Francisco/Bay Area, New York City): $123,000 - $164,000 USD per year.

• Mid-High Range (Boston, Los Angeles, Seattle, Washington DC): $113,000 - $151,000 USD per year.

• Mid Range (Arlington, Denver, San Diego, Sacramento): $108,000 - $144,000 USD per year.

• Lower-Mid Range (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 - $131,000 USD per year.

• Lowest Range (Baton Rouge, Birmingham, Charleston, Cincinnati, Cleveland, Daytona Beach, Indianapolis, Nashville, New Orleans, Omaha, Phoenix, Pittsburgh, St. Louis, Tampa): $95,000 - $127,000 USD per year.

Benefits:

• Stock Options: Opportunity to invest in the company's growth and potential future success.

• Work-from-Home Stipend: A dedicated stipend provided in the first year to help set up an effective home office environment.

• Medical, Vision, and Dental Coverage: Comprehensive health insurance plans for employees and their families.

• Life Insurance: Basic life insurance coverage to provide financial security.

• Paid Time Off: Generous PTO policy with 20 vacation days accrued annually, plus 11 paid holidays.

• Parental Leave: 16 weeks of paid leave for birthing parents (after six months of employment) and 8 weeks of paid bonding leave for non-birthing parents.

• Retirement Savings: Access to a 401(k) plan, including a company contribution that is subject to a vesting schedule.

• Commuter Benefits: Options to assist with commuting costs and convenience.

• Professional Development Stipend: A dedicated budget to support continuous learning and skill enhancement.

Working Hours: The role is structured around a standard 40-hour work week, typical for full-time positions. However, given the remote nature and mission-driven aspect, there may be flexibility, but core collaboration hours will likely apply.

📝 Enhancement Note: The salary ranges are explicitly provided and vary by location. Candidates should consider their specific location and research the upper end of the range for their region. The benefits package is comprehensive, with notable offerings like stock options, a WFH stipend, and generous parental leave, which are attractive to many professionals.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology / Health Services (specifically focused on Medicaid benefits and community-based care delivery). Waymark operates at the intersection of technology and social impact, aiming to transform care for underserved populations.

Company Size: While not explicitly stated, the description mentions being the "second designer" and a "growing team," suggesting a startup or early-stage growth company, likely in the range of 50-200 employees. This implies a dynamic, fast-paced environment where individual contributions have a significant impact.

Founded: The company's founding date is not provided, but the focus on transforming care and building technology suggests a relatively modern organization, likely founded within the last decade, aligning with the rise of health tech and value-based care models.

Team Structure:

• The Product Design team currently consists of one existing designer, and this role will be the second.

• The designer will report to the Head of Product, indicating a clear leadership structure within the product function.

• This role will collaborate closely with Product Management, Engineering, and Data Science teams, fostering a cross-functional and collaborative environment.

• The company culture emphasizes values of Bold Builders, Humble Learners, Experiment to Improve, and Focused Urgency. Methodology:

• Data-Driven Decisions: The company values using data to inform decisions and continuously assess performance.

• Experimentation: A culture of experimentation is encouraged to drive improvement.

• Participatory Design: A core methodology involves designing with and learning from the communities served, valuing lived experiences.

• Human-Centered Approach: The focus is on creating technology that amplifies human impact and removes barriers to care.

Company Website: [Waymark Website URL would be inserted here if available, but based on context, it's likely waymark.com]

📝 Enhancement Note: The emphasis on being the "second designer" is key. It signifies a critical juncture for the design function—opportunity to define processes, establish best practices, and influence the design system's growth. The company's values (Bold Builders, Humble Learners, Experiment to Improve, Focused Urgency) are central to their operational ethos and should be reflected in an applicant's approach and communication.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Senior Product Designer. While not directly an "operations" role in the traditional sense of RevOps or SalesOps, it sits within the product development lifecycle, which is integral to GTM (Go-To-Market) strategy and operational execution. The seniority implies a high degree of autonomy, the ability to lead design initiatives, and contribute to product strategy.

Reporting Structure: The Senior Product Designer will report directly to the Head of Product. This provides a clear line of communication and mentorship, as well as direct exposure to product leadership.

Operations Impact: The impact of this role is significant. By designing user-friendly and effective technology for community-based care teams and Medicaid patients, the designer directly influences:

• Healthcare Outcomes: Improving patient health and access to care.

• Operational Efficiency: Reducing manual labor for care teams, combating burnout, and enabling them to serve more patients effectively.

• Scalability: Creating robust, user-centered systems that can scale to meet growing demand.

• User Adoption: Ensuring the technology is adopted and valued by its users.

Growth Opportunities:

• Design Leadership: As the second designer, there's a strong potential to grow into a lead design role, mentoring future hires and shaping the design team's direction.

• Skill Specialization: Opportunity to deepen expertise in areas like AI/ML product design, conversational design, participatory design, and healthcare technology compliance.

• Cross-functional Expertise: Gaining deep experience collaborating with product, engineering, and data science teams, understanding the full product development lifecycle.

• Domain Expertise: Developing specialized knowledge in Medicaid healthcare delivery, community health programs, and social determinants of health.

• Strategic Influence: Contributing directly to product strategy and company mission, impacting the future of healthcare delivery for underserved communities.

📝 Enhancement Note: This role is a significant step for a product designer looking to make a tangible impact in a mission-driven environment. The growth potential is tied to both design leadership and strategic product influence, particularly within a specialized and impactful sector like healthcare for underserved populations.

🌐 Work Environment

Office Type: Fully Remote. This means the primary work environment will be a home office.

Office Location(s): United States. The company is open to hiring remote employees across the US, with specific salary bands tied to different geographic regions.

Workspace Context:

• Home Office Environment: Employees are expected to have a suitable home workspace conducive to focused work, with a provided stipend for initial setup.

• Digital Collaboration: The work environment will be heavily reliant on digital collaboration tools (e.g., Slack, Zoom, Figma, project management software) for communication and teamwork.

• Cross-functional Interaction: Opportunities for regular interaction with product managers, engineers, data scientists, and other designers through virtual meetings and collaborative platforms.

• Mission-Oriented Culture: The workspace is infused with the company's values, emphasizing collaboration, learning, and a drive to improve healthcare access.

Work Schedule: Standard 40-hour work week is implied for this full-time role. Given the remote, US-wide nature, coordination around core working hours will be essential for effective team collaboration. Flexibility may be available, but adherence to project timelines and team availability will be paramount.

📝 Enhancement Note: The fully remote nature requires strong self-discipline, proactive communication, and comfort with digital collaboration tools. Candidates should be prepared to articulate how they maintain productivity and engagement in a remote setting. The regional salary bands also suggest that applicants should be aware of their location's impact on compensation.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application, resume, and portfolio. Strong alignment with the minimum qualifications and a compelling portfolio are key.

• Hiring Manager Interview: Likely a discussion with the Head of Product to assess experience, alignment with company values, and understanding of the role's scope.

• Design Challenge/Portfolio Review: A deeper dive into your portfolio, potentially including a design exercise or presentation. This is where you'll demonstrate your design process, problem-solving skills, and ability to articulate design decisions. Be prepared to discuss your case studies in detail.

• Cross-functional Interviews: Meetings with members of the product, engineering, and/or data science teams to assess collaboration skills and technical understanding.

• Final Interview: Potentially with a company leader or founder to discuss cultural fit and long-term vision.

Portfolio Review Tips:

• Tell a Story: Structure your portfolio around 2-3 in-depth case studies that highlight your process, challenges, solutions, and impact.

• Focus on Process: Clearly articulate your design thinking, user research methodologies, and how you iterated based on feedback.

• Quantify Impact: Whenever possible, include metrics or qualitative data that demonstrate the positive outcomes of your designs (e.g., improved user efficiency, reduced error rates, increased patient engagement).

• Highlight Community & Healthcare: Emphasize any experience with user research in complex environments, participatory design, or designing for healthcare/mission-driven organizations.

• Showcase Tool Proficiency: Demonstrate your command of Figma or other relevant design tools through clear, well-organized mockups and prototypes.

• Address Compliance: If relevant, briefly touch upon your understanding of designing within regulated environments like healthcare.

Challenge Preparation:

• Anticipate Workflow Problems: Be ready to discuss how you would approach designing solutions for complex workflows, especially those involving care coordination or patient outreach.

• Practice Articulating Design Decisions: Be prepared to explain why you made specific design choices, linking them back to user needs, business goals, and company values.

• Understand Waymark's Mission: Research Waymark's work with Medicaid beneficiaries and community-based care. Be ready to speak about your passion for this mission and how your design skills can contribute.

• Prepare Questions: Have thoughtful questions ready for each interviewer about the team, product, challenges, and company culture.

📝 Enhancement Note: The interview process will heavily scrutinize the portfolio. Candidates should select case studies that best align with the role's requirements: complex workflows, user research (ideally participatory), and impact on user efficiency or outcomes. Be ready to defend your design choices and demonstrate a deep understanding of Waymark's mission.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly preferred, explicitly mentioned), Sketch, Adobe XD. Proficiency in at least one, with Figma being the strongest asset.

• User Research Tools: While not specified, expect to use tools for surveys, interviews, usability testing, and potentially remote collaboration platforms.

• Project Management: Tools like Jira, Asana, Trello, or similar are likely used for task tracking and team coordination.

Analytics & Reporting:

• Product Analytics: Tools like Amplitude, Mixpanel, Google Analytics, or custom internal dashboards may be used to track user behavior and feature adoption.

• Data Visualization: The team likely uses tools to visualize data for insights; experience with Tableau, Looker, or similar could be beneficial.

CRM & Automation:

• Proprietary CRM Platform: The role involves designing for Waymark's own CRM. Understanding CRM principles and user needs within such systems is key.

• AI/ML Integration: Experience designing workflows that incorporate AI-assisted features or machine learning outputs will be highly valued.

📝 Enhancement Note: Figma is explicitly mentioned as a preferred tool. Candidates should be highly proficient in Figma. Experience with AI-assisted workflows and designing for CRM platforms aligns directly with the core responsibilities. While specific analytics tools aren't named, a general understanding of product analytics and data-driven design is expected.

👥 Team Culture & Values

Operations Values:

• Bold Builders: A proactive, problem-solving mindset, willing to tackle complex challenges in care delivery using technology and community collaboration.

• Humble Learners: Openness to feedback, diverse perspectives, and a continuous drive to improve through learning and adaptation.

• Experiment to Improve: A data-informed approach to decision-making, with a focus on iterative testing and performance assessment.

• Focused Urgency: A strong sense of mission drives swift, determined action towards achieving meaningful results in healthcare access and outcomes.

• Inclusivity & Equity: A deep commitment to designing solutions that serve historically excluded communities, addressing disparities related to language, race, poverty, substance use, or sexual identity.

Collaboration Style:

• Cross-functional Integration: Close collaboration with product management, engineering, and data science is essential, requiring strong communication and partnership skills.

• Participatory & Co-design: A willingness to actively involve end-users (care teams and patients) in the design process, valuing their input and lived experiences.

• Feedback-Oriented: An environment that encourages constructive feedback on designs and processes to foster continuous improvement.

• Mission Alignment: Team members are united by a shared commitment to Waymark's mission, fostering a purpose-driven work environment.

📝 Enhancement Note: The company's stated values are not just corporate jargon; they are core to how Waymark operates. Applicants should demonstrate how their past work and personal values align with these principles, particularly "Bold Builders" and "Humble Learners," as well as the commitment to inclusivity and the mission.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Underserved Populations: Addressing the unique needs and barriers faced by Medicaid beneficiaries and community health workers, often with limited access to technology or digital literacy.

• Balancing Usability with Compliance: Creating intuitive and user-friendly experiences while adhering to strict healthcare regulations like HIPAA and accessibility standards.

• Integrating AI Trustfully: Designing AI-assisted workflows that are perceived as trustworthy, helpful, and do not detract from human-centered care.

• Navigating Startup Ambiguity: Working in a fast-paced startup environment with evolving priorities and the need for adaptability.

• Establishing Design Processes: As the second designer, there's an opportunity to help define and mature the design function, processes, and documentation.

Learning & Development Opportunities:

• Deep Domain Expertise: Gaining specialized knowledge in community-based Medicaid healthcare delivery, social determinants of health, and care coordination models.

• AI/ML Design Specialization: Developing expertise in designing for AI-powered features and conversational interfaces within a healthcare context.

• Design System Development: Contributing significantly to the growth and maturity of Waymark's design system.

• Leadership Potential: Opportunities to grow into a design leadership role, potentially managing future designers and influencing product direction.

• Impactful Mission: The chance to contribute directly to improving healthcare outcomes for vulnerable populations, offering a strong sense of purpose.

📝 Enhancement Note: The role offers significant growth potential by tackling complex, impactful challenges. Candidates should be prepared to discuss how they approach ambiguity, learn new domains, and contribute to building foundational design practices within a growing organization.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you used user research to identify a critical workflow problem and how you designed a solution to address it. What was the impact?" (Focus on process, user-centricity, and outcome.)

• "How would you approach designing an AI-assisted feature for community health workers that needs to feel trustworthy and enhance their work without replacing human judgment?" (Assess understanding of AI ethics, user trust, and human-computer interaction.)

• "Waymark uses a participatory design approach. How would you incorporate this into your design process when working with community health workers and patients?" (Demonstrate empathy, collaboration skills, and understanding of co-design principles.)

• "How do you ensure designs meet healthcare compliance standards like HIPAA and accessibility requirements? Walk us through your process." (Test knowledge of regulated environments and attention to detail.) Company & Culture Questions:

• "Waymark values 'Bold Builders' and 'Humble Learners.' Can you share an example from your career that demonstrates both of these qualities?" (Assess alignment with company values and self-awareness.)

• "What interests you about Waymark's mission to transform care for Medicaid beneficiaries?" (Gauge passion for the mission and understanding of the problem space.)

• "How do you approach collaboration with cross-functional teams (engineers, product managers, data scientists)?" (Evaluate teamwork and communication skills.)

• "Given this is a fully remote role, how do you ensure effective communication and collaboration with your team?" (Assess remote work strategies and proactivity.) Portfolio Presentation Strategy:

• Structure: Select 2-3 of your strongest case studies. For each, clearly define the problem, your role, the process you followed, the constraints you faced, your design solutions, and the outcomes/impact.

• Focus on Process: Emphasize your design thinking, research methods, iteration loops, and rationale behind key decisions. Use visuals effectively to illustrate your journey.

• Quantify Impact: If possible, present metrics or qualitative feedback that demonstrate the success of your designs. For this role, focus on workflow efficiency, user satisfaction, or improved patient care.

• Tailor to Waymark: Highlight projects that show experience with complex workflows, regulated industries, or mission-driven organizations. If you have experience with participatory design or AI, make sure to showcase it.

• Be Ready for Deep Dives: Prepare to answer detailed questions about any aspect of your portfolio.

📝 Enhancement Note: Be ready to discuss your portfolio in depth, specifically highlighting projects that demonstrate your ability to tackle complex workflow challenges, conduct user research (especially participatory), and design for regulated industries. Your understanding of Waymark's mission and values will be critical.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on Greenhouse.

• Tailor Your Resume: Highlight experience in product design, user research, Figma proficiency, and any relevant work in healthcare, AI, or mission-driven organizations. Emphasize achievements related to workflow optimization and user-centered design.

• Curate Your Portfolio: Select 2-3 of your most impactful case studies that align with Waymark's needs. Ensure they clearly demonstrate your design process, problem-solving skills, and impact, particularly focusing on user-centricity and workflow improvements.

• Prepare Your Narrative: Practice articulating your design process, rationale, and how your experience aligns with Waymark's mission and values. Be ready to discuss your portfolio in detail.

• Research Waymark: Understand their mission, values, and the challenges in community-based Medicaid healthcare. Prepare thoughtful questions to demonstrate your engagement and interest.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.