Product Designer, ICHRA

📍 Job Overview

Job Title: Product Designer, ICHRA

Company: Oscar Health

Location: San Francisco, California, United States

Job Type: Full-Time

Category: Product Design / UX Design

Date Posted: 2026-09-14

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

Remote Status: Fully Remote

🚀 Role Summary

• Design and deliver user-centric experiences for Oscar's ICHRA (Individual Coverage Health Reimbursement Arrangement) tooling and the broader Lucie Marketplace, focusing on employer-facing benefits management.

• Drive the end-to-end product design process, from initial user research and discovery through high-fidelity delivery and iterative improvements, ensuring a consistent and intuitive user experience.

• Collaborate closely with product management, engineering, research, data science, and operational stakeholders to translate complex requirements into elegant and scalable design solutions.

• Contribute to and advocate for the Oscar design language system (Anatomy), ensuring brand consistency and a high level of visual polish across all product touchpoints.

📝 Enhancement Note: This role is specifically focused on enterprise software design within the health insurance sector, requiring a strong understanding of complex workflows and data management for employers. The emphasis on ICHRA and the Lucie Marketplace indicates a need for expertise in B2B SaaS product design.

📈 Primary Responsibilities

• Define and refine user flows, wireframes, and high-fidelity mockups for the ICHRA platform and related Lucie Marketplace features, addressing complex employer needs for managing health plan contributions.

• Partner with Product Managers to translate business requirements, user needs, and technical constraints into actionable design specifications and user stories.

• Conduct user research, usability testing, and gather feedback from stakeholders to validate design decisions and uncover opportunities for improvement.

• Collaborate with engineers to ensure accurate implementation of designs, providing assets and detailed specifications throughout the development lifecycle.

• Contribute to the evolution of Oscar's design language system (Anatomy), ensuring consistency, scalability, and accessibility across the Lucie suite.

• Develop and maintain strong relationships with cross-functional partners, effectively communicating design rationale and advocating for user needs.

• Leverage AI-assisted design tools (e.g., Claude Code) and industry-standard tools like Figma to enhance design efficiency and collaboration.

• Ensure design solutions comply with all applicable healthcare industry regulations and compliance standards.

📝 Enhancement Note: The responsibility to "Become an expert on the product’s users and their journeys" highlights the critical need for deep user empathy and a proactive approach to understanding the employer and broker experience within the health benefits administration space.

🎓 Skills & Qualifications

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

Experience:

• 4+ years of experience in Product Design, UX Design, or a related role, with a proven track record of designing and shipping complex web and mobile interfaces.

• 2+ years of direct experience managing and collaborating with cross-functional stakeholders, including Product Managers, Engineers, and business leaders. Required Skills:

• Expert proficiency in product design and UX principles, with a strong understanding of user-centered design methodologies.

• Demonstrated ability to design and deliver complex, data-intensive interfaces for enterprise software or B2B platforms.

• Proficiency with design and prototyping tools, particularly Figma.

• Experience conducting user research, usability testing, and translating findings into actionable design improvements.

• Strong stakeholder management and communication skills, with the ability to present design concepts and rationale effectively.

• Familiarity with design systems and experience contributing to or utilizing them. Preferred Skills:

• Experience within the healthcare insurance industry, particularly with employer-sponsored benefits or ICHRA.

• Proficiency with AI-assisted design tools such as Claude Code for workflow optimization.

• Experience creating animated prototypes or detailed user flow diagrams to communicate complex interactions.

• A passion for design ethics, accessibility, and inclusive design practices.

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

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

• Experience with user research methodologies and rapid prototyping.

📝 Enhancement Note: The requirement for "2+ concrete examples of designing and shipping complex web and mobile interfaces" emphasizes the need for a robust portfolio showcasing end-to-end design ownership and successful product launches, particularly in enterprise or B2B contexts.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• At least two comprehensive case studies showcasing the design and successful launch of complex web or mobile interfaces, ideally within B2B, enterprise software, or workforce management domains.

• Demonstrate a deep understanding of the end-to-end design process, including problem definition, user research, ideation, prototyping, user testing, and final implementation.

• Clearly articulate your role, responsibilities, and contributions within each case study.

• Showcase your ability to manage stakeholders, collaborate with cross-functional teams, and navigate technical challenges.

• Highlight your proficiency with design tools like Figma and any experience with AI-assisted design tools. Process Documentation:

• Provide examples of how you have documented design processes, user flows, and system workflows to ensure clarity and alignment with engineering and product teams.

• Be prepared to discuss your approach to iterative design, user feedback integration, and continuous improvement of product interfaces.

• Showcase your ability to translate complex requirements and research insights into clear, actionable design artifacts.

📝 Enhancement Note: Given the focus on enterprise software and B2B platforms, the portfolio should emphasize the impact of design decisions on business objectives, user efficiency, and measurable outcomes for employers.

💵 Compensation & Benefits

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

Benefits:

• Comprehensive medical, dental, and vision insurance plans.

• 11 paid holidays per year.

• 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: Standard 40 hours per week, with flexibility expected for collaboration across time zones and to meet project deadlines.

📝 Enhancement Note: The stated salary range is a strong indicator of a mid-level to senior Product Designer role within a well-funded tech company in a high-cost-of-living area like San Francisco. The benefits package is comprehensive, reflecting Oscar Health's commitment to employee well-being and long-term engagement.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance / Health Technology (Insurtech)

Company Size: Oscar Health is a significant player in the health insurance market, employing over 1,000 individuals, indicating a structured yet growing organization with established processes and a clear mission.

Founded: Oscar Health was founded in 2012, positioning it as a modern health insurance company built on a technology-first approach, distinct from traditional, legacy insurers.

Team Structure:

• The Product Design team is part of a larger Product, Design, Data organization, reporting to the SVP, Product, Design, Data. This suggests a collaborative environment where design is integrated with product strategy and data insights.

• This role will work closely with a Senior Product Designer focused on ICHRA, implying a mentorship and collaborative structure within the ICHRA domain.

• Expect close partnerships with Product Managers, Engineers, Researchers, Data Scientists, and Operational Stakeholders, reflecting a highly cross-functional team dynamic common in tech companies. Methodology:

• Oscar Health emphasizes a "full stack technology platform" and "relentless focus on serving our members," indicating a data-driven and user-centric approach to product development.

• The mention of AI-assisted tools like Claude Code suggests an embrace of modern workflows and efficiency improvements in the design and development process.

• The design process involves close collaboration, iterative feedback loops (critiques), and a strong emphasis on user research to inform design decisions.

Company Website: https://hioscar.com/

📝 Enhancement Note: Oscar Health's foundation in technology and member-centricity suggests a culture that values innovation, user empathy, and data-informed decision-making. The integration of design within a broader Product, Design, Data organization points to a strategic view of design's impact on business outcomes.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a mid-level Product Designer capacity, requiring 4+ years of experience. It involves significant ownership and collaboration, moving beyond junior execution to strategic contribution and stakeholder management.

Reporting Structure: The Product Designer reports to the SVP, Product, Design, Data. This high-level reporting structure indicates that design is a critical component of the company's strategy and that the role has visibility at the executive level. The close partnership with a Senior Product Designer on ICHRA provides direct mentorship and guidance.

Operations Impact: As a Product Designer for ICHRA and the Lucie Marketplace, this role directly impacts Oscar Health's ability to serve employers and their employees. The design of these tools is crucial for the company's growth in the employer benefits space, influencing user adoption, operational efficiency, and overall customer satisfaction. Successful designs will contribute to revenue generation and market competitiveness.

Growth Opportunities:

• Skill Specialization: Deepen expertise in designing for complex B2B/enterprise software, particularly within the healthcare and benefits administration sectors.

• Leadership Development: Opportunity to grow into a Senior Product Designer role, mentor junior designers, and potentially lead design initiatives for specific product areas.

• Cross-functional Influence: Expand influence across product strategy, research, and engineering by consistently delivering high-impact design solutions and fostering strong collaborative relationships.

• Design System Contribution: Become a key contributor to and advocate for the Oscar design language system (Anatomy), potentially leading its evolution.

📝 Enhancement Note: The reporting structure to an SVP and the focus on a critical B2B product area suggest significant potential for career advancement within Oscar Health, particularly for designers who can demonstrate strategic thinking and impactful product delivery.

🌐 Work Environment

Office Type: While the role is advertised as fully remote, Oscar Health operates with a hub office model. Future work models may involve a hybrid presence at the hub office associated with the candidate's metro area (San Francisco). This suggests a company culture that values both remote flexibility and the potential for in-person collaboration.

Office Location(s): The primary remote work location specified is San Francisco, California. This implies that candidates should ideally be located within or willing to relocate to the San Francisco Bay Area for potential future hybrid work arrangements.

Workspace Context:

• The remote nature of the role necessitates a self-sufficient and productive home office environment, equipped with reliable internet access.

• Collaboration will heavily rely on digital tools like Figma, Slack, and video conferencing, fostering a virtual collaborative workspace.

• Opportunities for team interaction will likely occur through virtual design critiques, team meetings, and cross-functional project syncs.

Work Schedule: The standard work schedule is 40 hours per week. Flexibility is expected, especially when collaborating with teams in different time zones or during critical project phases. The emphasis on AI-assisted tools suggests an environment that supports efficient work practices.

📝 Enhancement Note: Although remote, the mention of potential future hybrid work in San Francisco indicates a company that values in-person connection and may offer opportunities for on-site collaboration in the future, requiring proximity to a hub office.

📄 Application & Portfolio Review Process

Interview Process:

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

• Portfolio Review & Initial Call: You will likely be asked to present your portfolio, focusing on 2-3 relevant case studies that demonstrate your experience with complex enterprise/B2B software, your design process, and your ability to drive features from discovery to delivery. This stage will assess your communication skills and design thinking.

• Design Challenge/Case Study: You may be given a take-home design challenge or an in-person/virtual case study exercise. This will assess your problem-solving skills, design execution, and ability to work within constraints relevant to Oscar's products (e.g., employer benefits management).

• Cross-functional Interviews: Interviews with Product Managers, Engineers, Researchers, and potentially other Designers to assess your collaboration style, technical understanding, and cultural fit within the team.

• Hiring Manager/SVP Interview: A final interview to discuss your overall experience, strategic thinking, and alignment with Oscar Health's mission and values.

Portfolio Review Tips:

• Focus on Impact: For each case study, clearly articulate the problem you were solving, your specific role and contributions, the design solutions you developed, and the measurable outcomes or impact achieved (e.g., increased user adoption, improved efficiency, positive user feedback).

• Showcase Process: Detail your design process, including user research methods, ideation techniques, prototyping, and testing. Explain why you made certain design decisions.

• Highlight B2B/Enterprise Experience: Prioritize case studies that demonstrate experience with complex interfaces, data-heavy platforms, or enterprise software, especially if they relate to HR tech, FinTech, or B2B SaaS.

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

• AI Tool Integration: If you've used AI tools like Claude Code, be prepared to discuss how they were integrated into your workflow and the benefits they provided.

Challenge Preparation:

• Understand the Domain: Research ICHRA, employer health benefits, and the general landscape of HR/benefits administration technology.

• Emphasize User Empathy: Focus on understanding the needs and pain points of employers, HR administrators, and potentially employees.

• Structure Your Response: Clearly outline your approach, assumptions, research methods (even if hypothetical), design solutions, and how you would measure success.

• Communicate Trade-offs: Be prepared to discuss design trade-offs and why you made certain decisions, especially when balancing user needs with technical or business constraints.

📝 Enhancement Note: The emphasis on complex enterprise software, stakeholder management, and a strong portfolio with concrete examples suggests that candidates should be ready to deep-dive into their past work and demonstrate a strategic, results-oriented approach to product design.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for UI design, wireframing, prototyping, and collaboration. Proficiency is essential.

• AI-Assisted Design Tools (e.g., Claude Code): Experience or willingness to learn and leverage AI tools to streamline the design-to-engineering process and enhance productivity.

Analytics & Reporting:

• Familiarity with analytics platforms (e.g., Amplitude, Mixpanel, Google Analytics) to understand user behavior and inform design decisions is beneficial.

• Ability to interpret data and translate insights into design improvements. CRM & Automation:

• While not directly a CRM role, understanding how design impacts user journeys within broader systems, including potential CRM integrations or workflows, is advantageous.

• Experience designing for systems that automate workflows or manage user data efficiently.

📝 Enhancement Note: Proficiency in Figma is a baseline requirement. The explicit mention of AI-assisted tools like Claude Code indicates a forward-thinking design team that values efficiency and modern workflows.

👥 Team Culture & Values

Operations Values:

• Member-Centricity: A core value at Oscar Health, meaning designs should prioritize the needs and well-being of members (in this case, employers and their employees).

• Innovation & Technology: Embracing new technologies and innovative approaches to solve healthcare challenges, including AI in design.

• Collaboration & Transparency: Working effectively across teams, sharing insights, and providing constructive feedback in design critiques.

• Data-Driven Decisions: Using research, data, and analytics to inform design choices and measure impact.

• Efficiency & Scalability: Designing solutions that are not only user-friendly but also efficient to build, maintain, and scale across the organization.

Collaboration Style:

• Cross-functional Partnership: Actively engaging with Product Managers, Engineers, Researchers, and Data Scientists to ensure a holistic approach to product development.

• Design Critiques: Participating in regular design critiques to give and receive constructive feedback, fostering a culture of continuous improvement.

• Knowledge Sharing: Contributing to the design team's collective knowledge through sharing best practices, insights, and learnings.

• Iterative Improvement: A willingness to iterate on designs based on feedback, testing results, and evolving business needs.

📝 Enhancement Note: The emphasis on "serving our members" and a "relentless focus" suggests a culture where user advocacy is paramount. Collaboration is framed as a key driver of success, with a strong emphasis on cross-functional teamwork and open feedback.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of Healthcare Benefits: Designing for the intricacies of ICHRA and employer benefits administration requires navigating complex regulations, diverse user needs, and significant data management.

• Balancing Enterprise Needs with User Experience: Creating intuitive and user-friendly interfaces for complex enterprise software that also meet stringent business and compliance requirements.

• Cross-functional Alignment: Ensuring consistent vision and execution across multiple departments (Product, Engineering, Data, Operations) can be challenging.

• Evolving Technology Landscape: Staying current with design tools, AI advancements, and best practices in a rapidly evolving tech environment.

Learning & Development Opportunities:

• Industry Expertise: Gaining deep knowledge of the health insurance and benefits administration industry.

• Advanced Design Skills: Developing expertise in designing for complex B2B platforms, data visualization, and potentially AI-integrated workflows.

• Mentorship: Learning from a Senior Product Designer and reporting to an SVP, providing exposure to strategic thinking and leadership.

• Design System Evolution: Contributing to and influencing the development of Oscar's internal design system (Anatomy).

📝 Enhancement Note: The challenges presented are inherent to working in the Insurtech space and on enterprise-level products. The growth opportunities are significant for a designer looking to specialize and advance within a mission-driven tech company.

💡 Interview Preparation

Strategy Questions:

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

• "How do you balance the needs of different stakeholders (e.g., product managers, engineers, business leaders) when making design decisions?" (Highlight collaboration, communication, and negotiation skills.)

• "Walk me through a project where you used user research to significantly impact a design decision. What was the outcome?" (Emphasize data-driven design and user advocacy.) Company & Culture Questions:

• "What interests you about Oscar Health and our mission to change healthcare?" (Research Oscar's mission, values, and recent news.)

• "How do you see AI tools like Claude Code fitting into the product design process?" (Show awareness of industry trends and express enthusiasm for efficiency.)

• "Describe your experience working within a design system. What are the benefits and challenges?" (Discuss your understanding of design consistency and scalability.) Portfolio Presentation Strategy:

• Storytelling: Frame each case study as a narrative – the problem, your journey, the solution, and the impact.

• Quantify Impact: Wherever possible, use metrics to demonstrate the success of your designs (e.g., "reduced task completion time by X%", "increased user satisfaction by Y%", "supported Z% of employer accounts").

• Show, Don't Just Tell: Use high-fidelity mockups, interactive prototypes, and clear visuals to illustrate your design solutions.

• Explain Your Role: Be explicit about your contributions, especially in team-based projects.

• Prepare for Q&A: Anticipate questions about your design choices, trade-offs, and how you handle feedback.

📝 Enhancement Note: Candidates should prepare to discuss their experience with enterprise software design, stakeholder management, and the specific challenges of the healthcare industry. Demonstrating an understanding of Oscar Health's mission and a proactive approach to leveraging modern design tools will be key.

📌 Application Steps

To apply for this Product Designer position:

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

• Curate Your Portfolio: Select 2-3 of your strongest case studies that best demonstrate your experience with complex web/mobile interfaces, B2B/enterprise software, and your end-to-end design process. Prioritize examples that showcase your impact on user experience and business outcomes.

• Tailor Your Resume: Highlight your 4+ years of product/UX design experience, specific skills in Figma and user research, and any experience with enterprise software, B2B platforms, or the healthcare industry. Quantify achievements where possible.

• Prepare Your Presentation: Practice walking through your portfolio case studies, focusing on clear storytelling, articulating your design process, detailing your contributions, and explaining the impact of your work. Be ready to discuss your experience with stakeholder management.

• Research Oscar Health: Familiarize yourself with Oscar Health's mission, values, product offerings (especially ICHRA and Lucie Marketplace if information is available), and recent company news to articulate your interest and cultural fit.

⚠️ 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.