Product Designer, ICHRA

📍 Job Overview

Job Title: Product Designer, ICHRA

Company: Oscar Health

Location: Los Angeles, California, United States

Job Type: Full-Time

Category: Product Design / UX/UI Design

Date Posted: 2026-09-14

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

Remote Status: Hybrid

🚀 Role Summary

• Design and deliver user-centric experiences for Oscar's ICHRA (Individual Coverage Health Reimbursement Arrangement) tooling, a critical component of the Lucie Marketplace.

• Drive the end-to-end product design process, from discovery and user research to high-fidelity delivery and iteration, ensuring a consistent and scalable user experience.

• Collaborate closely with cross-functional teams, including Product Management, Engineering, Research, Data Science, and Operations, to translate complex requirements into intuitive and effective design solutions.

• Leverage modern design workflows and AI-assisted tools like Claude Code alongside Figma to enhance design efficiency and streamline the handoff to engineering.

• Contribute to the broader Lucie ecosystem, encompassing direct enrollment platforms for brokers and the consumer marketplace, while maintaining a primary focus on ICHRA.

📝 Enhancement Note: This role is positioned within a growing health tech company that utilizes a modern, tech-driven approach to insurance. The emphasis on ICHRA tooling suggests a focus on B2B or employer-facing features, requiring a strong understanding of complex workflows and data management. The mention of AI-assisted tools indicates a forward-thinking design environment.

📈 Primary Responsibilities

• Define and meticulously craft user experiences for Oscar's ICHRA product suite, enabling employers to effectively manage health plan contributions for their employees.

• Conduct in-depth user research and usability testing to generate actionable insights, deeply understanding user needs and pain points within the ICHRA context.

• Act as a primary advocate for the user throughout the product development lifecycle, ensuring their needs are prioritized and addressed in design solutions.

• Own the design process for assigned features, from conceptualization and wireframing to high-fidelity mockups and interactive prototypes, ensuring alignment with product strategy and technical feasibility.

• Collaborate with product managers and tech leads to define product requirements, scope, and technical constraints, translating them into elegant and functional design solutions.

• Partner with engineers to ensure accurate implementation of designs, providing clear specifications and ongoing support throughout the development sprints.

• Contribute to and evolve Oscar's design language system (Anatomy), ensuring visual consistency and scalability across the Lucie platform.

• Work closely with other product designers across Oscar, participating in design critiques, sharing knowledge, and contributing to the overall design team's growth and best practices.

• Ensure all designed experiences comply with relevant healthcare regulations and accessibility standards.

📝 Enhancement Note: The responsibilities highlight a strong emphasis on user advocacy, cross-functional collaboration, and end-to-end design ownership. The mention of "Anatomy" as the design system suggests a mature design practice within Oscar.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field, or equivalent practical experience.

Experience: Minimum of 4+ years of professional experience in Product Design, UX Design, or a closely related field, with a demonstrated track record of shipping complex web and mobile interfaces.

Required Skills:

• Proven expertise in Product/UX Design methodologies, including user research, journey mapping, wireframing, prototyping, and usability testing.

• A strong portfolio showcasing 2+ concrete examples of designing and successfully shipping complex web and mobile interfaces, preferably within enterprise software or data-intensive platforms.

• Minimum of 2+ years of direct experience managing and influencing stakeholders across various departments (e.g., Product, Engineering, Business).

• Proficiency in design and prototyping tools, with a strong emphasis on Figma.

• Ability to translate complex requirements, business goals, and user research findings into simple, intuitive, and user-friendly UI designs.

• Experience in defining and working with design systems to ensure consistency and scalability.

• Excellent communication, presentation, and interpersonal skills, with the ability to articulate design decisions and rationale effectively to diverse audiences. Preferred Skills:

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

• Familiarity with AI-assisted design tools such as Claude Code to enhance workflow efficiency.

• Experience designing for workforce management tools, B2B platforms, or data-intensive applications.

• Proficiency in storytelling techniques, including creating animated prototypes and detailed user flow diagrams to communicate design intent.

• A deep interest in design ethics, accessibility standards (e.g., WCAG), and their application in the healthcare space.

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

• Experience with user research methodologies and conducting usability testing sessions.

📝 Enhancement Note: The requirements emphasize practical experience and a strong portfolio, particularly for complex interfaces. The preference for healthcare experience and AI tool familiarity suggests specific areas Oscar values for this role. The "2+ concrete examples" requirement for shipped interfaces is a key differentiator for portfolio review.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase 2+ complex web and mobile interfaces that have been successfully designed and shipped, demonstrating end-to-end ownership.

• Include case studies that detail your design process, from initial problem definition and user research through to final implementation and iteration.

• Clearly articulate the user problems you were solving, your design decisions, and the impact of your solutions, ideally with quantifiable results.

• Demonstrate experience with data-intensive platforms or enterprise software, highlighting how you managed complexity and user workflows.

• Highlight your collaboration with cross-functional teams (Product Managers, Engineers) and how you managed stakeholder expectations and feedback. Process Documentation:

• Provide examples of how you have documented design processes, including user flows, wireframes, and interaction specifications.

• Showcase your approach to conducting user research and usability testing, including how you synthesized findings into design improvements.

• Illustrate your experience working with or contributing to design systems, detailing how you ensured consistency and scalability.

• Be prepared to discuss how you leverage AI-assisted tools (like Claude Code) or other methods to streamline design-to-engineering handoffs.

📝 Enhancement Note: The portfolio should serve as a tangible representation of the candidate's ability to handle complex design challenges, collaborate effectively, and deliver polished, user-centered products within a tech-enabled environment. Emphasis on shipped products and process documentation is critical.

💵 Compensation & Benefits

Salary Range: $123,372.00 - $161,925.75 per year

Benefits:

• Comprehensive Medical, Dental, and Vision benefits.

• Participation in Oscar's unlimited vacation program, promoting work-life balance.

• Company equity grants, offering ownership and participation in Oscar's growth.

• Annual performance bonuses, recognizing contributions and achievements.

• 11 paid holidays per year.

• Paid sick time.

• Paid parental leave.

• 401(k) plan participation with potential company match.

• Life and disability insurance coverage.

• Paid wellness time and reimbursements to support employee well-being.

Working Hours: Standard full-time role, likely aligning with Pacific Time Zone business hours, with a hybrid work schedule requiring 3 days in the Los Angeles office per week, including a mandatory Thursday. The total expected work hours are approximately 40 per week.

📝 Enhancement Note: The salary range is competitive for a Product Designer role in Los Angeles with the specified experience level. The benefits package is robust, reflecting Oscar's commitment to employee well-being and engagement, with a notable emphasis on unlimited vacation and wellness support.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance Technology / Health Tech

Company Size: Oscar Health is a significant player in the health insurance market, employing over 1,000 individuals (based on typical company size for a publicly traded tech-enabled insurer). This size indicates a structured environment with established processes but also room for innovation and impact.

Founded: 2012. Oscar was founded with a vision to revolutionize health insurance through technology and a member-centric approach. This relatively young founding date suggests a culture that is agile, innovative, and embraces modern technologies and methodologies.

Team Structure:

• The Product Design team operates within a larger Product, Design, Data organization, reporting to the SVP, Product, Design, Data.

• This role will collaborate closely with Product Managers, Engineers, Data Scientists, Researchers, and Operational Stakeholders, indicating a highly cross-functional and collaborative team environment.

• The role focuses on the "Lucie Marketplace" and specifically "ICHRA tooling," suggesting specialized sub-teams or focus areas within the broader product organization. Methodology:

• Oscar emphasizes a tech-first, data-driven approach to improving healthcare accessibility and affordability.

• Expect a blend of agile development methodologies, user-centered design principles, and a focus on iterative improvement based on user feedback and data analysis.

• The integration of AI-assisted tools like Claude Code signals a commitment to leveraging cutting-edge technology for efficiency and innovation in design and development workflows.

Company Website: https://hioscar.com/

📝 Enhancement Note: Oscar's culture is built on innovation and a mission to improve healthcare. The size and founding date suggest a dynamic environment that balances established practices with a startup mentality. The cross-functional nature of the teams is crucial for operations professionals to understand for collaboration.

📈 Career & Growth Analysis

Operations Career Level: Mid-Senior Level Product Designer. This level implies ownership of significant features, the ability to work autonomously, and a strong influence on design strategy and execution within their domain (ICHRA tooling). They are expected to mentor junior designers and contribute to design system evolution.

Reporting Structure: The Product Designer reports to the SVP, Product, Design, Data. They will work closely with a Senior Product Designer focused on ICHRA and will collaborate with Product Managers and Engineering Leads on a daily basis. This structure provides visibility to senior leadership while maintaining close collaboration with product teams.

Operations Impact: This role has a direct impact on the usability and effectiveness of Oscar's employer-facing health insurance management tools. By designing intuitive ICHRA experiences, the Product Designer will contribute to employer satisfaction, operational efficiency for businesses using Oscar, and ultimately, the accessibility and affordability of health insurance for employees, aligning directly with Oscar's core mission.

Growth Opportunities:

• Specialization: Deepen expertise in health insurance product design, specifically within complex B2B or employer-facing solutions like ICHRA.

• Leadership: Potential to grow into a Senior Product Designer role, leading design initiatives for larger product areas, mentoring junior designers, or taking on design management responsibilities.

• Skill Development: Opportunity to become proficient in advanced AI-assisted design tools, contribute to the evolution of a robust design system, and gain experience in the complex healthcare technology landscape.

• Cross-functional Exposure: Develop stronger strategic partnerships with Product Management, Engineering, and Data teams, enhancing understanding of business drivers and technical complexities.

📝 Enhancement Note: The role offers substantial growth potential within a specialized and impactful area of health tech. The hybrid structure and reporting line suggest a balanced approach to autonomy and mentorship, fostering career advancement.

🌐 Work Environment

Office Type: Hybrid work model with a physical office presence required in Los Angeles. This implies a blend of remote flexibility and in-person collaboration.

Office Location(s): Los Angeles, California. Specific office details would be provided upon hiring, but the expectation is a modern office space conducive to collaborative work.

Workspace Context:

• The Los Angeles office will serve as a hub for team meetings, collaborative design sessions, and fostering company culture. Thursdays are designated as a mandatory in-office day for team-wide engagement.

• Expect a dynamic, fast-paced environment typical of a growing tech company.

• Access to modern design tools, collaboration platforms, and potentially state-of-the-art office amenities.

• Opportunities for informal and formal interactions with design, product, engineering, and data teams, fostering a strong sense of community and shared purpose.

Work Schedule: The role is full-time, with approximately 40 working hours per week. The hybrid schedule offers flexibility, with 3 days in the office and 2 days remote. This structure aims to balance focused individual work with essential team collaboration and idea exchange.

📝 Enhancement Note: The hybrid model in Los Angeles offers a balance for professionals who value both focused remote work and the benefits of in-person collaboration. The designated in-office day ensures consistent team cohesion.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review applications and portfolios to assess basic qualifications and alignment with the role.

• Portfolio Review & Design Challenge: Candidates will likely present their portfolio, focusing on 2-3 key projects that demonstrate their experience with complex interfaces, B2B/enterprise design, and their design process. A design challenge, potentially involving a real-world problem or scenario, may be assigned to assess problem-solving skills and design thinking.

• Cross-functional Interviews: Interviews with Product Managers, Engineers, and potentially other Designers to evaluate collaboration style, technical understanding, and ability to articulate design decisions.

• Hiring Manager Interview: A final interview with the SVP, Product, Design, Data to discuss overall fit, strategic thinking, and long-term vision.

Portfolio Review Tips:

• Highlight ICHRA/Enterprise Focus: Prioritize projects that showcase experience with complex workflows, data management, B2B tools, or enterprise software. If direct ICHRA experience is limited, draw parallels from other complex domains.

• Demonstrate Process: Clearly outline your design process for each project, emphasizing user research, problem definition, ideation, iteration, and how you incorporated feedback.

• Quantify Impact: Wherever possible, present metrics or outcomes that demonstrate the success of your designs (e.g., increased user engagement, improved task completion rates, reduced error rates).

• Showcase Collaboration: Include examples or discussions about how you worked with cross-functional teams and managed stakeholder expectations.

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

Challenge Preparation:

• Understand ICHRA: Research the basics of ICHRA and its role in employer benefits to grasp the context of the design challenge.

• Focus on User Needs: For any given problem, identify the key user personas (employers, employees, administrators) and their primary pain points.

• Structure Your Thinking: Be prepared to articulate your problem-solving approach logically, from understanding the problem to proposing a solution and justifying your design choices.

• Consider Technical Constraints: Acknowledge that design solutions must be feasible within technical limitations.

📝 Enhancement Note: The interview process is structured to assess a blend of design skills, process thinking, collaboration abilities, and cultural fit. A strong, relevant portfolio is paramount, and candidates should be prepared to articulate their design process and impact.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core design and prototyping tool for creating interfaces, user flows, and high-fidelity mockups. Proficiency is essential.

• AI-Assisted Design Tools: Familiarity with tools like Claude Code for streamlining design-to-engineering workflows is a significant advantage.

• Prototyping Tools: Beyond Figma, experience with other prototyping tools (e.g., InVision, ProtoPie) may be beneficial for specific use cases.

Analytics & Reporting:

• Data Analysis Tools: Experience with tools like Tableau, Looker, or similar platforms to understand user behavior, identify trends, and measure the impact of design decisions.

• User Analytics Platforms: Familiarity with tools like Google Analytics, Mixpanel, or Amplitude to track user interactions and feature adoption.

CRM & Automation:

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

• Collaboration Platforms: Proficiency in tools like Slack and Google Workspace for communication and document sharing.

📝 Enhancement Note: The emphasis on Figma and AI-assisted tools like Claude Code highlights Oscar's commitment to modern, efficient design practices. Understanding how design integrates with data analytics and project management tools is crucial for success in this role.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to Oscar's mission of making healthcare affordable and accessible through innovation and technology.

• User-Centricity: A deep focus on understanding and advocating for the needs of Oscar's members and employer clients.

• Collaboration: A belief in the power of cross-functional teamwork to solve complex problems and drive impact.

• Innovation & Agility: A willingness to experiment, adapt, and leverage new technologies (like AI) to improve processes and outcomes.

• Data-Informed: Decisions are guided by data analysis and user insights, ensuring that design solutions are effective and impactful.

Collaboration Style:

• Cross-functional Integration: Designers work hand-in-hand with Product Managers, Engineers, and Data Scientists, fostering a shared sense of ownership and understanding.

• Open Critiques: A culture of constructive feedback through design critiques, where ideas are shared openly and respectfully to elevate the quality of the product.

• Knowledge Sharing: Encouragement of sharing best practices, learnings, and insights across the design team and broader organization.

• Iterative Improvement: A continuous feedback loop where designs are tested, refined, and improved based on user feedback and performance data.

📝 Enhancement Note: Oscar's culture appears to be a blend of mission-driven purpose, user empathy, and a pragmatic, data-informed approach to innovation. Collaboration is key, with designers expected to be active participants in cross-functional teams.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of ICHRA: Designing for the intricacies of ICHRA, including employer contributions, employee choices, and compliance, presents a significant design challenge requiring deep understanding and careful navigation.

• Balancing B2B and B2C Needs: While focusing on ICHRA (often B2B-facing), the role may require considering the downstream impact on the end-user (employees) and ensuring a cohesive experience across the Lucie Marketplace.

• Technical Constraints: Navigating the technical limitations of a complex software platform while delivering elegant and functional design solutions.

• Healthcare Regulations: Adhering to strict regulations and compliance requirements within the healthcare industry, which can influence design possibilities.

Learning & Development Opportunities:

• Specialized Domain Expertise: Gaining deep knowledge in health insurance technology, particularly in the rapidly evolving ICHRA space.

• AI Tool Proficiency: Becoming an expert user of AI-assisted design tools to enhance productivity and explore new design possibilities.

• Design System Contribution: Playing a key role in evolving and maintaining Oscar's design system ("Anatomy"), contributing to its scalability and usability.

• Cross-Functional Strategic Influence: Developing a stronger voice in product strategy by collaborating closely with Product Management and Engineering leadership.

📝 Enhancement Note: The challenges presented are inherent to working in a complex, regulated industry like health tech. The growth opportunities are substantial, focusing on specialization, technological adoption, and strategic influence.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design a complex workflow for a B2B or enterprise product. What were the key challenges, and how did you approach them?" (Focus on process, user research, and stakeholder management).

• "How would you approach designing an ICHRA management tool for employers? What are the critical user needs and potential pain points you'd prioritize?" (Demonstrate understanding of the domain and problem-solving approach).

• "Discuss your experience working with design systems. How do you ensure consistency and scalability in your designs, and how might you contribute to Oscar's 'Anatomy' system?" (Highlight system thinking and practical application). Company & Culture Questions:

• "What interests you about Oscar Health and our mission to improve healthcare?" (Show genuine interest and alignment with company values).

• "Describe your ideal collaborative environment. How do you typically work with Product Managers and Engineers?" (Assess cultural fit and teamwork capabilities).

• "How do you stay updated on design trends and new technologies, such as AI-assisted tools?" (Demonstrate a commitment to continuous learning). Portfolio Presentation Strategy:

• Tell a Story: Frame each case study as a narrative: the problem, your approach, the solutions, and the outcome.

• Focus on Impact: Clearly articulate the "why" behind your design decisions and the measurable impact of your work.

• Show, Don't Just Tell: Use high-fidelity mockups, interactive prototypes, and user flow diagrams to illustrate your designs effectively.

• Be Prepared for Questions: Anticipate questions about your process, challenges, and decision-making. Be ready to dive deep into specific aspects of your projects.

• Highlight Collaboration: Discuss how you partnered with cross-functional teams and managed stakeholder feedback.

📝 Enhancement Note: Interview preparation should focus on articulating a clear design process, demonstrating experience with complex systems, and showcasing an understanding of Oscar's mission and values. The portfolio presentation is a critical component.

📌 Application Steps

To apply for this Product Designer position:

• Submit your application through the provided link on the Oscar Health careers page.

• Tailor Your Resume: Highlight your 4+ years of Product/UX Design experience, specifically mentioning any experience with complex web/mobile interfaces, enterprise software, or B2B platforms. Quantify achievements where possible.

• Curate Your Portfolio: Select 2-3 of your strongest case studies that best represent your experience in designing and shipping complex interfaces. Prioritize projects that align with B2B, data-intensive, or workflow-heavy applications. Clearly articulate your design process, user research, and the impact of your work.

• Prepare for the Design Challenge: Research ICHRA basics and think about potential user pain points for employers and employees. Be ready to articulate your thought process for solving design problems.

• Research Oscar Health: Familiarize yourself with Oscar's mission, values, and recent news to demonstrate genuine interest and cultural alignment during interviews.

⚠️ 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.