Product Designer, ICHRA

📍 Job Overview

Job Title: Product Designer, ICHRA

Company: Oscar Health

Location: Boston, Massachusetts, United States

Job Type: Full-Time

Category: Product Design / UX Design

Date Posted: September 14, 2026

Experience Level: Mid-Senior Level (2-5 years)

Remote Status: Fully Remote (Boston, MA)

🚀 Role Summary

• Design and deliver intuitive user experiences for Oscar's Lucie Marketplace, specifically focusing on ICHRA (Individual Coverage Health Reimbursement Arrangement) tooling.

• Drive product features from initial discovery and user research through high-fidelity delivery, ensuring a consistent and scalable experience across the Lucie suite.

• Collaborate closely with product managers, engineers, researchers, data scientists, and operational stakeholders to translate complex requirements into user-centered design solutions.

• Leverage modern design workflows, including AI-assisted tools like Claude Code and Figma, to enhance design-to-engineering process efficiency.

• Advocate for user needs and pain points by becoming an expert on user journeys within the ICHRA and broader Lucie ecosystem.

📝 Enhancement Note: This role is positioned within Oscar Health's Product Design team, with a specific focus on the ICHRA product suite. The emphasis on complex enterprise software, data-intensive platforms, and workforce management tools suggests a need for a designer skilled in B2B SaaS or complex platform design, rather than purely consumer-facing applications. The mention of "Lucie Marketplace" and "ICHRA tooling" indicates a focus on employer-sponsored benefits management, a sophisticated area within health tech.

📈 Primary Responsibilities

• Define and craft user experiences that empower employers to effectively manage health plan contributions for their employees through ICHRA.

• Conduct comprehensive user research and usability testing to gather actionable insights that inform and validate design decisions.

• Own the end-to-end design process for features, from conceptualization and wireframing to high-fidelity mockups and interactive prototypes.

• Partner with product managers and tech leads to clarify product strategy, align on solutions, and ensure successful feature implementation.

• Contribute to the evolution and maintenance of Oscar's design language system, "Anatomy," ensuring visual consistency and brand integrity across all product touchpoints.

• Translate complex requirements, business goals, and user research findings into simple, intuitive, and visually compelling user interfaces.

• Collaborate effectively within a cross-functional team environment, providing and receiving thoughtful feedback during design critiques.

• Ensure design solutions comply with all applicable laws and regulations within the healthcare industry.

• Contribute to other areas of the Lucie ecosystem (e.g., direct enrollment platform for brokers, consumer marketplace) as needed, demonstrating flexibility and broad design capability.

📝 Enhancement Note: The responsibilities highlight a need for a designer who can operate at both strategic and tactical levels. "Owning the design process" implies significant autonomy, while "partnering closely with cross-functional peers" emphasizes strong collaborative skills. The explicit mention of user research and usability testing indicates a data-driven design approach is expected.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field is often preferred for roles of this nature and experience level.

Experience: 4+ years of progressive experience in Product Design and UX Design, with a strong emphasis on designing and shipping complex web and mobile interfaces.

Required Skills:

• Proven expertise in Product Design and UX Design methodologies.

• A strong visual design portfolio showcasing complex web and mobile interface design, with at least two concrete examples of shipped products.

• Demonstrated experience in managing stakeholders directly and effectively communicating design decisions and rationale (2+ years).

• Proficiency in design and prototyping tools, specifically Figma.

• Experience leveraging AI-assisted tools to streamline design processes (e.g., Claude Code).

• Ability to conduct user research and usability testing, translating findings into actionable design improvements.

• Strong understanding of design systems and experience contributing to or maintaining them (e.g., Oscar's "Anatomy").

• Excellent communication, collaboration, and presentation skills, with the ability to articulate design strategy to diverse audiences. Preferred Skills:

• Experience within the healthcare industry, understanding its unique complexities and regulatory landscape.

• Proficiency in storytelling techniques, such as creating animated prototypes or detailed user flow diagrams.

• Interest and knowledge in design ethics, accessibility standards, and inclusive design practices, particularly relevant to healthcare.

• Evidence of contributions to internal tools, system workflows, or power-user interfaces.

• Proven ability to navigate technical constraints and deliver effective design solutions.

• A genuine, inquisitive, humble, yet determined professional demeanor.

📝 Enhancement Note: The requirement for "2+ concrete examples of designing and shipping complex web and mobile interfaces" and "2+ years managing stakeholders directly" suggests the company is looking for candidates with demonstrable experience in delivering tangible results and navigating organizational dynamics, not just theoretical design knowledge. The emphasis on "complex" interfaces points towards B2B or enterprise-level product design challenges.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least two significant projects demonstrating the design and successful shipment of complex web and mobile interfaces.

• Highlight projects that involved designing for enterprise software, data-intensive platforms, or workforce management tools, if applicable.

• Clearly articulate your role and contributions within each project, especially in cross-functional team settings.

• Demonstrate your process from discovery through delivery, including user research, ideation, wireframing, prototyping, and final UI design.

• Include examples of how you have managed stakeholders and incorporated their feedback.

• Showcase visual design quality and attention to detail in user interface design. Process Documentation:

• Present case studies that detail your approach to problem-solving, emphasizing user-centered design principles.

• Illustrate how you conducted user research and usability testing, and how those insights directly influenced design outcomes.

• Document your workflow for collaborating with product managers, engineers, and other stakeholders, showing how alignment was achieved.

• If possible, include examples of how you've contributed to or utilized design systems.

• Demonstrate your ability to translate complex requirements into streamlined and intuitive user flows.

📝 Enhancement Note: Given the focus on complex enterprise software and stakeholder management, the portfolio should not only display visual design skills but also evidence of strategic thinking, problem-solving capabilities, and the ability to navigate the complexities of product development in a regulated industry. Demonstrating a structured design process is critical.

💵 Compensation & Benefits

Salary Range: $123,372.00 - $161,925.75 per year. This range is for the base salary and is competitive for a Product Designer role with 4+ years of experience in a major metropolitan area like Boston, especially within the tech and health insurance sectors.

Benefits:

• Comprehensive medical, dental, and vision benefits.

• 11 paid holidays.

• Paid sick time.

• Paid parental leave.

• 401(k) plan participation.

• Life and disability insurance.

• Paid wellness time and reimbursements.

• Unlimited vacation program.

• Company equity grants.

• Annual performance bonuses.

Working Hours: The standard working hours are not explicitly stated but are typically around 40 hours per week for a full-time role. The remote nature and unlimited vacation program suggest some flexibility, but core working hours for collaboration will likely be expected.

📝 Enhancement Note: The salary range provided is specific and falls within the expected market rate for a mid-to-senior level Product Designer in Boston, MA. The extensive list of benefits, including unlimited vacation, equity, and bonuses, indicates a strong total compensation package. The mention of "unlimited vacation" implies a results-oriented culture where employees are trusted to manage their time effectively.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance & Technology. Oscar Health is a disruptive force in the health insurance market, leveraging technology to create a more accessible, affordable, and member-centric healthcare experience. This intersection of health tech and insurance implies a dynamic environment that values innovation, data-driven decision-making, and a strong mission-driven approach.

Company Size: Oscar Health is a significant player in the health insurance market, indicated by its established presence and growth. While the exact size isn't provided in the raw data, its operations suggest a medium to large-sized organization with a strong tech focus. This size typically means established processes but also opportunities for impact and growth within specialized teams.

Founded: Oscar Health was founded in 2012, positioning it as a relatively modern player in the insurance industry, built with a technology-first ethos from its inception. This history suggests a culture that values innovation, agility, and a departure from traditional insurance models.

Team Structure:

• The Product Design team likely includes Senior Product Designers, Product Designers (this role), and potentially UX Researchers, UI Designers, and Design Operations specialists.

• The role reports into the SVP, Product, Design, Data, indicating a high level of visibility and strategic importance for the design function.

• The designer will collaborate closely with Product Managers, Tech Leads, Engineers, Data Scientists, and Operational Stakeholders, requiring strong cross-functional partnership skills. Methodology:

• Data-driven decision-making is a core tenet, with close collaboration with Data Scientists and a focus on user research and usability testing.

• A modern workflow is emphasized, including the use of AI-assisted tools and Figma for design and engineering collaboration.

• Iterative design and development are expected, with features moving from discovery through delivery.

• A strong focus on user empathy and understanding user journeys is critical to delivering on Oscar's mission.

Company Website: https://hioscar.com/

📝 Enhancement Note: Oscar Health's mission to make healthcare affordable and accessible, combined with its technology-centric approach, suggests a culture that values innovation, user advocacy, and measurable impact. The reporting structure to an SVP highlights the strategic importance of design within the organization.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Product Designer, likely falling into the mid-to-senior level category. It requires significant experience (4+ years) and the ability to manage stakeholders, indicating a level of autonomy and responsibility beyond junior design roles. The focus is on designing and shipping complex features, suggesting a path towards Senior Product Designer or specialized design leadership.

Reporting Structure: The role reports to the SVP, Product, Design, Data. This high-level reporting structure offers excellent visibility and the opportunity to influence product strategy and design direction at an executive level. It also suggests a mature design organization where design is integrated into the core product development lifecycle.

Operations Impact: The Product Designer's work directly impacts Oscar's mission by shaping the tools that enable employers to manage health plan contributions. This has a direct effect on the accessibility and affordability of health insurance for employees, contributing significantly to the company's value proposition and member experience. The design of ICHRA tooling, in particular, can streamline administrative processes for employers and improve the clarity of benefits for employees.

Growth Opportunities:

• Skill Advancement: Opportunity to deepen expertise in designing complex B2B SaaS products, health tech regulations, and advanced design system utilization. Potential to become a subject matter expert in ICHRA or other complex benefit administration areas.

• Leadership Potential: With demonstrated success and stakeholder management skills, there's a clear path to a Senior Product Designer role, potentially leading design initiatives or mentoring junior designers.

• Cross-Functional Exposure: Working closely with product management, engineering, and data science provides exposure to various business functions, fostering a holistic understanding of product development and business strategy.

• Broader Product Influence: The ability to contribute to other areas of the Lucie suite offers opportunities to broaden design impact and gain experience across different user segments and product functionalities.

📝 Enhancement Note: Reporting to an SVP provides a unique opportunity for mentorship and high-level strategic exposure. The role is not just about executing designs but about influencing product direction, making it attractive for designers looking to grow beyond pure execution.

🌐 Work Environment

Office Type: The position is advertised as fully remote, with the candidate residing in Boston, MA. While currently remote, the description notes that "future models could potentially involve a hybrid presence at the hub office associated with your metro area." This suggests a flexible approach that may evolve towards a hybrid model in the future, but the immediate expectation is remote work.

Office Location(s): While the role is remote, the candidate must reside in Boston, MA. This implies Oscar Health has a significant presence or hub in the Boston area, which may be relevant for potential future hybrid arrangements or local team meetups.

Workspace Context:

• Remote Collaboration: Expect to work in a highly collaborative remote environment, utilizing digital tools for communication, design, and project management.

• Technology Stack: Access to modern design tools like Figma and AI-assisted coding tools (Claude Code) will be integral to the daily workflow.

• Team Interaction: Regular interaction with cross-functional teams (product, engineering, data, operations) will be facilitated through virtual meetings, design critiques, and shared digital workspaces. The culture likely encourages proactive communication and asynchronous collaboration.

Work Schedule: The core working hours are not explicitly defined but are expected to align with standard business operations (likely around 40 hours/week). Given the remote nature and "unlimited vacation program," there's likely an emphasis on flexible scheduling and achieving results rather than strict adherence to a 9-to-5, though collaboration windows will be necessary.

📝 Enhancement Note: The "remote first" approach, with a potential for future hybrid engagement, is a key aspect of the work environment. Candidates should be comfortable with remote collaboration tools and proactive communication. The Boston location requirement for remote workers suggests a strong regional presence.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess experience, skills, and alignment with the role's requirements.

• Design Challenge/Case Study: You will likely be asked to present a case study from your portfolio that demonstrates your design process, problem-solving skills, and ability to deliver complex solutions. This might involve a live presentation or a take-home assignment focused on a relevant problem.

• Cross-Functional Interviews: Interviews with Product Managers, Engineers, and potentially other designers or stakeholders to assess collaboration style, technical understanding, and fit with the team.

• Hiring Manager Interview: A discussion with the SVP, Product, Design, Data (or a delegate) to evaluate strategic thinking, leadership potential, and overall fit with Oscar Health's vision and culture.

Portfolio Review Tips:

• Focus on Process: Clearly articulate your design process for each project, from discovery and research to iteration and final delivery.

• Showcase Complexity: Highlight projects that demonstrate your ability to handle complex user flows, data-heavy interfaces, or enterprise software challenges.

• Quantify Impact: Where possible, use metrics to demonstrate the impact of your design solutions (e.g., improvements in user task completion, engagement, or efficiency).

• Stakeholder Management: Include examples or narratives of how you managed stakeholder expectations and incorporated feedback effectively.

• Visual Polish: Ensure your portfolio is visually appealing, well-organized, and easy to navigate. High-fidelity mockups and prototypes are essential.

• Tailor to Oscar: If possible, subtly tailor your presentation to align with Oscar Health's mission and the specific challenges of the healthcare/insurance industry.

Challenge Preparation:

• Understand ICHRA: Research ICHRA and the broader landscape of employer benefits administration to grasp the user needs and business context.

• Design Thinking: Be prepared to walk through your thought process for solving a design problem, emphasizing user empathy and iterative refinement.

• Collaboration Scenarios: Think about how you would approach collaboration with engineers, product managers, and other stakeholders in a remote, fast-paced environment.

• AI Tool Integration: Be ready to discuss how you leverage tools like Figma and AI assistants in your workflow.

📝 Enhancement Note: The emphasis on "complex enterprise software" and "stakeholder management" in the job description suggests the interview process will heavily scrutinize these areas. Candidates should be prepared to deep-dive into their portfolio projects, explaining the "why" behind their design decisions and how they navigated challenges.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Explicitly mentioned as a key tool for design and collaboration. Proficiency in Figma for wireframing, UI design, prototyping, and design system management is essential.

• AI-Assisted Tools: Mention of "Claude Code" indicates an expectation or encouragement to use AI tools to augment the design and development process, potentially for code generation, documentation, or ideation.

Analytics & Reporting:

• Data Analysis Tools: While not explicitly named, the role involves close collaboration with data scientists and a focus on user research and usability testing. Experience with analytics platforms (e.g., Google Analytics, Amplitude, Mixpanel) or the ability to interpret data from them would be beneficial for understanding user behavior and measuring design impact.

• Prototyping Tools: Beyond Figma, familiarity with other prototyping tools for specific use cases (e.g., Principle, ProtoPie for complex animations) might be advantageous.

CRM & Automation:

• Internal Tools: The mention of "contribution to internal tools" and "system workflows" suggests that familiarity with or the ability to design for internal operational tools is a plus.

• Collaboration Platforms: Proficiency with remote collaboration tools such as Slack, Zoom, and project management software (e.g., Jira, Asana) is assumed for effective remote teamwork.

📝 Enhancement Note: The explicit mention of Figma and AI tools like Claude Code points to a modern, tech-forward design environment. Candidates should highlight their experience with these specific tools and demonstrate an openness to integrating AI into their workflow.

👥 Team Culture & Values

Operations Values:

• User Empathy: A deep understanding of and advocacy for user needs and pain points is paramount, driving the mission to make healthcare accessible and affordable.

• Data-Driven Decision Making: Design decisions are informed by user research, usability testing, and quantitative data analysis, ensuring solutions are effective and impactful.

• Collaboration & Transparency: A strong emphasis on cross-functional teamwork, open communication, and sharing feedback within the design team and with partner teams.

• Innovation & Agility: A culture that encourages exploring new technologies (like AI in design) and adapting quickly to evolving market needs and user expectations.

• Mission-Oriented: A shared commitment to Oscar Health's mission to transform healthcare, fostering a sense of purpose in the work.

Collaboration Style:

• Cross-Functional Integration: Designers work seamlessly with Product Managers, Engineers, Data Scientists, and Operations to ensure alignment and successful product delivery.

• Design Critiques: Regular participation in design critiques to provide and receive constructive feedback, fostering continuous improvement and shared learning.

• Proactive Communication: In a remote setting, a proactive and clear communication style is essential for keeping stakeholders informed and facilitating smooth workflows.

• Iterative Feedback Loops: Embracing feedback as a continuous process to refine designs and ensure they meet user needs and business objectives.

📝 Enhancement Note: Oscar Health's values likely revolve around innovation, user-centricity, and a mission-driven approach. The emphasis on collaboration and data-driven decisions is key for a Product Designer in this environment, especially when working on complex B2B products.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complexity: The ICHRA product suite involves intricate rules, regulations, and user flows typical of enterprise B2B software, requiring a designer capable of simplifying complexity.

• Balancing Stakeholder Needs: Navigating diverse stakeholder requirements and priorities while advocating for user needs and design best practices.

• Healthcare Industry Nuances: Understanding the specific regulatory environment, user behaviors, and ethical considerations within the healthcare and insurance sectors.

• Remote Collaboration: Effectively contributing and collaborating within a fully remote team, requiring strong communication and self-management skills.

• Evolving Technology: Staying abreast of advancements in design tools and AI, and integrating them effectively into workflows.

Learning & Development Opportunities:

• Specialized Design Expertise: Deepen knowledge in designing for complex financial/benefits administration platforms and the healthcare tech space.

• Leadership Development: Opportunities to mentor junior designers, lead design initiatives, and influence product strategy.

• Industry Exposure: Gain insights into the health insurance industry's operational and technological challenges, and contribute to solutions that improve healthcare access.

• Tool Proficiency: Master advanced features of Figma and explore new AI-driven design tools to enhance productivity and creativity.

• Cross-Functional Skill Building: Develop a stronger understanding of product management, engineering principles, and data analytics through close collaboration.

📝 Enhancement Note: The primary challenge will be translating complex regulatory and financial requirements into user-friendly experiences. Growth opportunities are strong, particularly for those looking to specialize in health tech or move into design leadership.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a complex enterprise software feature. What were the biggest challenges, and how did you overcome them?" (Focus on process, user research, and stakeholder management.)

• "How do you approach user research and usability testing for a product like ICHRA, where users might have diverse technical skills and specific compliance needs?" (Emphasize methodology, insight generation, and iteration.)

• "Walk me through your process for collaborating with product managers and engineers on a new feature. How do you ensure alignment and manage feedback?" (Highlight communication, negotiation, and teamwork.) Company & Culture Questions:

• "What interests you about Oscar Health and our mission to transform healthcare?" (Connect your values and career goals to the company's mission.)

• "How do you see yourself contributing to our design culture, especially in a remote environment?" (Discuss collaboration style, feedback approach, and proactive communication.)

• "How do you measure the success of your design work, especially in terms of user adoption and business impact?" (Prepare to discuss metrics and ROI, linking design to business outcomes.) Portfolio Presentation Strategy:

• Structure Your Case Studies: For each project, clearly define the problem, your role, the design process, key decisions, solutions, and outcomes. Use visuals effectively.

• Tell a Story: Frame your projects as narratives that highlight your problem-solving journey and the impact you made.

• Quantify Results: Whenever possible, use data and metrics to demonstrate the tangible results of your design work.

• Demonstrate Technical Understanding: Be prepared to discuss technical constraints you encountered and how you worked with engineers to find solutions.

• Showcase Collaboration: Explain how you partnered with various stakeholders and incorporated their feedback.

• Practice Your Pitch: Rehearse your presentation to ensure it's concise, engaging, and within the allotted time.

📝 Enhancement Note: The interview will likely be a deep dive into your portfolio and design process. Be prepared to articulate the "why" behind every decision and how your work directly contributed to business objectives and user satisfaction within a complex domain.

📌 Application Steps

To apply for this Product Designer position:

• Submit your application through the Oscar Health careers portal via the provided Greenhouse link.

• Customize Your Resume: Tailor your resume to highlight your 4+ years of Product/UX Design experience, specifically mentioning complex web/mobile interfaces, stakeholder management, and any relevant experience in health tech or enterprise software. Use keywords from the job description.

• Curate Your Portfolio: Select 2-3 of your strongest projects that best showcase your ability to design complex interfaces, your full design process, and your stakeholder management skills. Ensure case studies are clear, visually compelling, and demonstrate quantifiable impact where possible.

• Prepare Your Presentation: Practice presenting your portfolio case studies, focusing on storytelling, clear articulation of your process, and demonstrating how you solve problems and drive impact. Be ready to discuss your experience with Figma and AI tools.

• Research Oscar Health: Familiarize yourself with Oscar Health's mission, values, and recent product developments. Understand the ICHRA product and its significance in the health insurance market.

⚠️ 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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