Product Designer, ICHRA

📍 Job Overview

Job Title: Product Designer, ICHRA

Company: Oscar Health

Location: New York, New York, 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: Hybrid

🚀 Role Summary

• Design and deliver user-centered experiences for Oscar's ICHRA (Individual Coverage Health Reimbursement Arrangement) tooling within the Lucie Marketplace.

• Drive the end-to-end design process for complex enterprise software, from discovery and research through high-fidelity delivery and implementation.

• Collaborate closely with product management, engineering, research, data science, and operational stakeholders to ensure seamless user journeys and scalable solutions.

• Advocate for user needs and pain points, translating them into intuitive and visually compelling product designs that align with Oscar's mission.

• Contribute to and leverage Oscar's design language system (Anatomy) to maintain consistency and brand integrity across all product touchpoints.

📝 Enhancement Note: This role focuses on Product Design within the Health Insurance sector, specifically for a B2B2C platform (Lucie Marketplace) enabling employers to manage employee health benefits. The emphasis on ICHRA and enterprise software suggests a need for understanding complex workflows, data management, and stakeholder communication in a regulated industry. The mention of AI-assisted tools like Claude Code alongside Figma indicates a forward-thinking approach to design and development workflows.

📈 Primary Responsibilities

• Define and design user experiences for Oscar's users, enabling a wide array of use cases that contribute to making healthier lives affordable and accessible.

• Become an expert on the product’s users and their journeys, advocating their needs and pain points to the larger organization.

• Own the design process, partnering closely with cross-functional peers like product managers, tech leads, engineers, data scientists, and business stakeholders to drive clarity around strategy and alignment on solutions.

• Collaborate with other product designers across the organization, providing feedback during critiques and contributing thoughtfully to the design team at large.

• Conduct user research and usability testing with a clear focus on generating actionable insights to drive informed design decisions.

• Design visually compelling experiences for all users and contribute to the Oscar design language system (Anatomy).

• Bring the Oscar brand to life in product experiences, ensuring a cohesive and engaging user interface.

• Ensure compliance with all applicable laws and regulations within the healthcare industry.

📝 Enhancement Note: The responsibilities highlight a deep involvement in the entire product lifecycle, from foundational user research to final design delivery and compliance. The emphasis on "owning the design process" and "advocating for user needs" suggests a need for strong product sense and the ability to influence product direction based on user insights.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's degree in Design, HCI, Computer Science, or a related field is often preferred for Product Designer roles. Relevant certifications or a strong portfolio can sometimes substitute for formal education.

Experience: 4+ years of experience in Product/UX Design, with a proven track record of designing and shipping complex web and mobile interfaces. Requires 2+ years of experience managing stakeholders directly.

Required Skills:

• Product Design (4+ years)

• UX Design (4+ years)

• Visual Design

• Complex Web and Mobile Interface Design (2+ concrete examples required)

• Stakeholder Management (2+ years)

• User Research and Usability Testing

• Design System Contribution (e.g., Anatomy)

• Figma proficiency

• Strong understanding of UI principles and best practices

• Ability to translate requirements, goals, and research into simple and useful UI Preferred Skills:

• Experience in the healthcare space

• Experience designing enterprise software, data-intensive platforms, or workforce management tools

• Storytelling techniques (e.g., animated prototypes, user flow diagrams)

• Interest in design ethics, accessibility, and healthcare-specific topics

• Experience with AI-assisted design tools (e.g., Claude Code)

• Proven record of navigating technical constraints to deliver design solutions

• Experience with internal tools, system workflows, and power-user interfaces

• 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" indicates a need for demonstrable experience and strong communication skills, not just theoretical knowledge. The "Bonus points" section points towards candidates who can bring specific industry or technical expertise to the role.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least two complex web and mobile interface design projects, detailing the problem, your process, design decisions, and shipped outcomes.

• Demonstrate experience in designing for enterprise software, data-intensive platforms, or workforce management tools, highlighting the complexity and impact of your solutions.

• Include examples of how you have managed stakeholders, showing your communication strategy and ability to gain alignment on design solutions.

• Present work that illustrates your contribution to or utilization of design systems, emphasizing consistency and scalability.

• If applicable, include examples of user research, usability testing, and how insights informed your design iterations and final product. Process Documentation:

• Clearly articulate your design process, from initial user research and discovery through wireframing, prototyping, user testing, and final high-fidelity design delivery.

• Detail how you collaborate with product managers, engineers, and other cross-functional partners throughout the design lifecycle.

• Show how you incorporate user feedback and data-driven insights to iterate on designs and ensure successful product launches.

• Illustrate your approach to advocating for user needs and translating them into tangible design solutions that address business objectives.

📝 Enhancement Note: The emphasis on "shipping complex web and mobile interfaces" and stakeholder management strongly suggests that the portfolio should not just be conceptual but demonstrate real-world impact and the ability to navigate the complexities of product development and stakeholder alignment in a corporate environment.

💵 Compensation & Benefits

Salary Range: $123,372.00 - $161,925.75 per year. This range is indicative of a mid-to-senior level Product Designer role in a major metropolitan area like New York City, reflecting the experience requirements and the company's positioning.

Benefits:

• Medical, dental, and vision benefits

• 11 paid holidays

• Paid sick time

• Paid parental leave

• 401(k) plan participation

• Life insurance

• Disability insurance

• Paid wellness time and reimbursements

• Unlimited vacation program

• Company equity grants

• Annual performance bonuses

Working Hours: This is a full-time position, likely requiring approximately 40 hours per week. The hybrid model specifies 3 days in the office per week, with Thursdays being a required in-office day for team meetings and events. The other two office days are flexible.

📝 Enhancement Note: The provided salary range is competitive for a Product Designer in New York City with the specified experience level. The comprehensive benefits package, including unlimited vacation, equity, and bonuses, further enhances the overall compensation. The hybrid work arrangement with designated in-office days is typical for roles requiring significant cross-functional collaboration.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance / Health Technology. Oscar Health operates within the highly regulated and dynamic health insurance sector, leveraging technology to disrupt traditional models. This context implies a need for designers to understand compliance, user privacy, and the critical nature of healthcare services.

Company Size: Oscar Health is a significant player in the health insurance market, indicating a structured organization with established processes, but also with a culture that likely fosters innovation given its tech-forward approach. This size suggests opportunities for impact within a larger framework and potential for cross-team collaboration.

Founded: Oscar Health was founded in 2012, positioning it as a relatively modern health insurance company built on a technology platform, aiming to differentiate from legacy insurers. This history suggests a culture that values innovation, agility, and a user-centric approach to healthcare.

Team Structure:

• The Product Design team likely consists of various specialists, including Product Designers, UX Designers, and potentially UI Designers or UX Researchers.

• This role reports into the SVP, Product, Design, Data, indicating a high level of visibility and direct access to senior leadership within these critical functions.

• Cross-functional collaboration is central, with designers working closely with Product Managers, Engineers, Data Scientists, and Operational Stakeholders to bring products to life. Methodology:

• Data-driven decision-making is a core component, with an emphasis on user research, usability testing, and leveraging data to inform design.

• Workflow planning and optimization are key, particularly for enterprise tools like ICHRA, where efficiency and ease of use for employers are paramount.

• Automation and efficiency practices are likely encouraged, especially with the mention of AI-assisted tools, aiming to streamline the design-to-development pipeline.

Company Website: https://hioscar.com/

📝 Enhancement Note: Oscar Health's identity as a tech-first health insurer suggests a culture that values innovation, data, and user-centricity. 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 at a Mid-Senior level, requiring 4+ years of experience. It implies a level of autonomy and responsibility for complex features or product areas, moving beyond junior design tasks to owning significant parts of the product lifecycle. The focus on ICHRA and enterprise tooling suggests a specialization within B2B2C product design.

Reporting Structure: Reporting directly to the SVP, Product, Design, Data, provides a clear line of sight to executive leadership and opportunities to influence broader product and design strategy. This also suggests that design decisions are highly valued and considered at a strategic level.

Operations Impact: The Product Designer will have a direct impact on the usability and effectiveness of the Lucie Marketplace, specifically the ICHRA tools. This directly affects employers' ability to manage health benefits for their employees, influencing operational efficiency, employee satisfaction, and Oscar's competitive positioning in the benefits administration space.

Growth Opportunities:

• Skill Specialization: Deepen expertise in designing for complex enterprise software, B2B SaaS, or the healthcare tech domain.

• Leadership Development: Potential to mentor junior designers, lead design initiatives for specific product areas, or evolve into a Senior Product Designer role with greater strategic influence.

• Cross-Functional Acumen: Develop a strong understanding of business operations, product management, and engineering processes within a fast-paced tech environment.

• Design System Evolution: Contribute to the growth and refinement of Oscar's design language system (Anatomy), potentially taking ownership of specific components or guidelines.

📝 Enhancement Note: The role offers a clear path for growth from a mid-level individual contributor to a more senior or specialized role, with direct exposure to executive leadership and a significant impact on a key product offering.

🌐 Work Environment

Office Type: This position is based in Oscar Health's New York City office, requiring a hybrid work schedule. The office environment is designed to foster collaboration, team meetings, and company events.

Office Location(s): New York City, NY. Specific details regarding office accessibility or amenities would typically be available upon inquiry or during the interview process.

Workspace Context:

• The hybrid model (3 days in-office, with Thursdays as a core team day) facilitates both focused individual work and collaborative team sessions.

• Designers will have access to modern design tools and technology, including Figma and potentially AI-assisted tools like Claude Code, supporting an efficient design-to-development workflow.

• Opportunities for direct interaction with cross-functional teams (Product, Engineering, Data) are built into the hybrid schedule, promoting a cohesive and integrated work environment.

Work Schedule: The standard work schedule is full-time, with flexibility in choosing two of the three in-office days. This allows for a balance between structured team collaboration and personal work preferences, accommodating the needs of design processes that often require deep focus.

📝 Enhancement Note: The hybrid work model is structured to balance the benefits of in-person collaboration with the flexibility of remote work, ensuring that team cohesion and cross-functional alignment are maintained.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review your application and portfolio to assess your experience and fit. Be prepared to highlight your most relevant projects.

• Design Challenge/Case Study: You may be asked to complete a design exercise or present a case study from your portfolio that demonstrates your problem-solving skills, design process, and ability to handle complex requirements. Focus on the ICHRA or similar enterprise tooling if possible.

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

• Hiring Manager/SVP Interview: A final interview, likely with the SVP, Product, Design, Data, to discuss your strategic thinking, leadership potential, and overall alignment with Oscar Health's culture and goals.

Portfolio Review Tips:

• Highlight ICHRA/Enterprise Experience: Prioritize projects that showcase your ability to design complex web and mobile interfaces, particularly those related to enterprise software, data-intensive platforms, or workforce management tools.

• Show, Don't Just Tell: For each project, clearly articulate the problem, your role, the design process undertaken (research, ideation, iteration, testing), key decisions made, and the measurable outcomes or impact. Use visuals, user flows, and prototypes effectively.

• Demonstrate Stakeholder Management: Include examples or discussions on how you managed communication, feedback, and alignment with stakeholders throughout the design process.

• Detail Your Process: Explain your approach to user research, usability testing, and how you translated insights into design solutions.

• Design System Contribution: If you have experience with design systems, showcase how you've contributed to or leveraged them for consistency and scalability.

• AI Tool Integration (Optional but beneficial): If you've used AI tools like Claude Code to enhance your workflow, mention it and explain the benefits.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with ICHRA, health insurance benefits administration for employers, and common pain points for HR professionals and employees.

• Focus on Problem-Solving: Be prepared to tackle a design problem that requires analytical thinking, user empathy, and creative solutions.

• Articulate Your Thinking: Clearly explain your rationale behind design decisions, trade-offs considered, and how your solution addresses the defined problem and user needs.

• Practice Presentation Skills: Rehearse presenting your portfolio and any case studies or challenges to ensure clarity, conciseness, and impact.

📝 Enhancement Note: The interview process emphasizes practical application of design skills, collaboration, and strategic thinking, with a strong focus on portfolio content that demonstrates real-world impact and experience with complex systems.

🛠 Tools & Technology Stack

Primary Tools:

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

• AI-Assisted Design Tools (e.g., Claude Code): Mentioned as a tool to streamline the design-to-engineering process, indicating an openness to leveraging AI for efficiency.

• Prototyping Tools: Beyond Figma's capabilities, other tools might be used for advanced prototyping or animated user flows.

Analytics & Reporting:

• User Research Platforms: Tools for conducting user interviews, usability testing, and gathering feedback.

• Data Analysis Tools: While not a primary responsibility, understanding how to interpret data from tools like Amplitude, Mixpanel, or internal dashboards is beneficial for informing design decisions.

CRM & Automation:

• Internal Tools: Oscar likely uses various internal systems for operations, member management, and broker interactions. Familiarity with designing for such systems is a plus.

• Design System Management: Tools or processes for managing and evolving the "Anatomy" design language system.

📝 Enhancement Note: Proficiency in Figma is a baseline requirement. The mention of AI-assisted tools suggests a modern workflow, and an understanding of how design integrates with data analytics and internal operational systems will be advantageous.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and serving the needs of Oscar's members, employers, and brokers, driving design decisions with user empathy.

• Innovation & Agility: A culture that embraces new technologies and approaches (like AI-assisted design) to improve healthcare delivery and operational efficiency.

• Collaboration: Strong emphasis on cross-functional teamwork, open communication, and mutual respect among product, engineering, design, and operations teams.

• Data-Driven Approach: Utilizing data, research, and analytics to inform strategy, measure impact, and continuously improve product experiences.

• Mission-Driven: A shared dedication to Oscar's mission of making healthcare affordable and accessible, fostering a sense of purpose in the work.

Collaboration Style:

• Cross-functional Integration: Designers are expected to be integrated team members, working hand-in-hand with product managers and engineers from discovery through delivery.

• Feedback Culture: Regular design critiques and feedback sessions are integral to the design process, promoting continuous improvement and shared ownership.

• Knowledge Sharing: Encouraging the sharing of best practices, design patterns, and learnings across the design team and with other departments.

📝 Enhancement Note: The culture at Oscar Health appears to be a blend of a mission-driven, user-focused healthcare organization with a fast-paced, tech-oriented approach, emphasizing collaboration and data-informed decision-making.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Healthcare Complexity: Designing for a regulated industry like healthcare requires a nuanced understanding of compliance, privacy, and the sensitive nature of health information.

• Balancing Enterprise and Consumer Needs: The Lucie Marketplace serves both employers (enterprise users) and employees (consumers), requiring designs that cater to different user needs, technical proficiencies, and goals.

• Driving Adoption of New Technologies: Effectively integrating new tools and methodologies, such as AI-assisted design, while ensuring team buy-in and successful implementation.

• Maintaining Design Consistency: Ensuring a cohesive and scalable user experience across different product areas (ICHRA, broker platform, consumer marketplace) within the Lucie ecosystem.

Learning & Development Opportunities:

• Healthcare Domain Expertise: Gaining in-depth knowledge of health insurance products, regulations, and the unique challenges faced by employers and employees.

• Enterprise SaaS Design: Developing specialized skills in designing for complex business workflows, administrative tools, and B2B user bases.

• Advanced Design Methodologies: Exploring and applying cutting-edge design practices, including AI integration and advanced prototyping techniques.

• Leadership and Mentorship: Opportunities to grow into senior design roles, lead product initiatives, and mentor emerging talent within the design team.

📝 Enhancement Note: The role presents opportunities to tackle complex challenges within a critical industry, fostering specialized skill development and offering clear pathways for career advancement.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design a complex workflow for enterprise users. What were the key challenges, and how did you ensure usability and efficiency?" (Focus on process, stakeholder management, and outcome.)

• "How do you approach balancing the needs of different user groups (e.g., employers vs. employees) within a single platform?" (Highlight user research, segmentation, and design trade-offs.)

• "Tell me about a time you had to advocate for a design decision that faced resistance from stakeholders. How did you navigate that situation, and what was the result?" (Emphasize communication, data-driven arguments, and conflict resolution.) Company & Culture Questions:

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

• "How do you see yourself contributing to our hybrid work environment and collaborative culture?" (Connect your work style to the described culture and team structure.)

• "How do you measure the success of your design work beyond user satisfaction?" (Discuss metrics, business impact, and ROI.) Portfolio Presentation Strategy:

• Structure: Organize your portfolio logically, perhaps by project type or by impact. For each project, clearly state the problem, your role, the process, key decisions, and the outcomes/learnings.

• Storytelling: Craft a narrative for each case study, highlighting the user problem, your design journey, and the impact of your solution. Use visuals effectively to illustrate your points.

• Focus on Process: Be prepared to walk through your design process in detail, explaining your rationale at each step, especially how you incorporated research and stakeholder feedback.

• Quantify Impact: Where possible, use metrics to demonstrate the success of your designs (e.g., improved conversion rates, reduced error rates, increased user engagement).

• Prepare for Questions: Anticipate questions about your design choices, challenges encountered, and how you would approach similar problems in the future.

📝 Enhancement Note: The interview preparation should focus on demonstrating a strong understanding of the design process, user advocacy, stakeholder management, and the ability to translate complex business needs into effective user experiences, particularly within the healthcare and enterprise software context.

📌 Application Steps

To apply for this Product Designer position:

• Submit your application through the provided link on greenhouse.io.

• Curate Your Portfolio: Select 2-3 of your most impactful projects that best showcase your experience with complex web/mobile interfaces, enterprise software, and stakeholder management. Ensure each project clearly outlines the problem, your process, design decisions, and shipped outcomes.

• Optimize Your Resume: Tailor your resume to highlight keywords from the job description, such as "Product Design," "UX Design," "ICHRA," "Enterprise Software," "Stakeholder Management," and "Figma." Quantify your achievements wherever possible.

• Prepare Your Presentation: Rehearse walking through your portfolio, focusing on clear storytelling, explaining your design process, and articulating the impact of your work. Be ready to discuss how you'd approach designing for ICHRA.

• Research Oscar Health: Understand the company's mission, values, and recent work in the health insurance and technology space. Familiarize yourself with the Lucie Marketplace and the concept of ICHRA to better align your application and interview responses.

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