Product Designer, ICHRA at Oscar Health

📍 Job Overview

Job Title: Product Designer, ICHRA

Company: Oscar Health

Location: San Francisco, California, United States

Job Type: Full-Time

Category: Product Design / UX/UI Design

Date Posted: August 14, 2026

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

Remote Status: Fully Remote (San Francisco, CA residents only)

🚀 Role Summary

Design and deliver user-centric product experiences for Oscar's ICHRA (Individual Coverage Health Reimbursement Arrangement) marketplace, focusing on employer tools for health plan contribution management.
Collaborate closely with product managers, engineers, researchers, data scientists, and operational stakeholders to drive features from initial discovery through high-fidelity delivery.
Contribute to a consistent, scalable, and intuitive user experience across the broader Lucie suite, including direct enrollment platforms for brokers and consumer marketplaces.
Leverage AI-assisted tools like Claude Code alongside Figma to streamline the design-to-engineering process and enhance design workflow efficiency.

📝 Enhancement Note: The role is specifically for Product Designer focused on ICHRA tooling within the larger Lucie Marketplace ecosystem. While the primary focus is ICHRA, the candidate will contribute to other areas as needed. The job description emphasizes a blend of visual design expertise and experience with complex enterprise software, data-intensive platforms, or workforce management tools, suggesting a need for a designer capable of handling intricate systems and user flows.

📈 Primary Responsibilities

Define and design user experiences that enable a wide array of use cases, directly supporting Oscar's mission to make healthier lives affordable and accessible.
Become an expert on the product's users and their journeys, acting as a strong advocate for their needs and pain points within the organization.
Own the end-to-end design process, from user research and ideation to high-fidelity prototyping and delivery, ensuring alignment with product strategy and technical feasibility.
Collaborate with cross-functional peers, including product managers, tech leads, engineers, data scientists, and business stakeholders, to drive clarity around strategy and achieve alignment on solutions.
Conduct user research and usability testing to generate actionable insights that inform and guide design decisions, ensuring a user-centered approach.
Design visually compelling interfaces and contribute to the Oscar design language system, "Anatomy," ensuring brand consistency and a cohesive user experience.
Bring the Oscar brand to life within product experiences, creating engaging and memorable interactions for users.
Ensure compliance with all applicable laws and regulations within the healthcare space.

📝 Enhancement Note: The responsibilities highlight a significant degree of ownership and cross-functional leadership. The emphasis on "owning the design process" and "advocating for user needs" suggests that the candidate will be expected to influence product direction and drive consensus among diverse teams, a common expectation for mid-to-senior level operations-adjacent design roles.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design, Human-Computer Interaction, or a related field, or equivalent practical experience, is often preferred for Product Designer roles.

Experience:

Minimum of 4 years of experience in Product/UX Design.
At least 2 years directly managing stakeholders, demonstrating strong communication and influence skills.
Proven track record of designing and shipping complex web and mobile interfaces, evidenced by at least 2 concrete examples. Required Skills:
Expertise in Product/UX Design principles and methodologies.
Strong visual design skills with a robust portfolio showcasing complex interface design.
Proficiency in design tools such as Figma.
Experience with AI-assisted design tools, specifically mentioning Claude Code.
Demonstrated ability to conduct user research and perform usability testing.
Proven experience in stakeholder management and cross-functional collaboration.
Ability to translate complex requirements, goals, and research findings into simple, intuitive UI designs. Preferred Skills:
Experience within the healthcare industry or with health insurance products.
Proficiency in storytelling techniques, including animated prototypes or detailed user flow diagrams.
Interest in design ethics, accessibility, and other relevant topics within the healthcare domain.
Experience contributing to internal tools, system workflows, and power-user interfaces.
Proven ability to navigate technical constraints and deliver effective design solutions.
Experience with user research and prototyping tools beyond Figma.

📝 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 a candidate who can demonstrate not just design craft but also project ownership, delivery success, and effective interpersonal skills within a collaborative environment. The mention of AI tools suggests a forward-thinking approach to design workflows.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

At least two detailed case studies showcasing the end-to-end design process for complex web or mobile interfaces that have been shipped to market.
Demonstrations of how user research and usability testing insights were integrated into the design process to drive informed decisions and improve user outcomes.
Examples of contributions to design systems or style guides, illustrating an understanding of scalability and consistency (e.g., using "Anatomy").
Evidence of designing for complex systems, data-intensive platforms, or workforce management tools, highlighting problem-solving skills in intricate domains. Process Documentation:
Case studies should clearly articulate the problem statement, user needs, design challenges, your role and process, key design decisions, and quantifiable outcomes or lessons learned.
Showcase proficiency in using tools like Figma for wireframing, prototyping, and high-fidelity design, and potentially Claude Code for workflow enhancement.
Illustrate the ability to collaborate with product managers and engineers, demonstrating how design requirements were translated into technical specifications and delivered effectively.

📝 Enhancement Note: Given the emphasis on "complex enterprise software, data-intensive platforms, or workforce management tools," a strong portfolio should highlight the candidate's ability to manage complexity, define intricate user flows, and demonstrate a structured approach to problem-solving within these domains. The inclusion of AI tools suggests a portfolio might also touch upon how technology was leveraged to improve design efficiency.

💵 Compensation & Benefits

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

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: The standard working hours are implied to be 40 hours per week, typical for a full-time role. The remote nature of the position offers flexibility in how these hours are managed, within the needs of cross-functional collaboration.

📝 Enhancement Note: The salary range provided is specific and falls within the typical range for a Product Designer with 4+ years of experience in a high-cost-of-living area like San Francisco, especially within the tech/health-tech sector. The comprehensive benefits package, including unlimited vacation and equity, is competitive for the industry.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance Technology (HealthTech). Oscar Health is innovating within the healthcare industry by leveraging technology to create a more member-centric and affordable insurance experience.

Company Size: Oscar Health is a significant player in the health insurance market, indicated by its presence on the stock market and its focus on technology. The company size implies a structured environment with established processes, but also opportunities for impact.

Founded: Oscar was founded in 2012 with the mission to create a better health insurance company, acting like a "doctor in the family." This founding principle likely informs a culture of empathy, member advocacy, and innovation.

Team Structure:

The Product Design team is part of a larger Product, Design, Data organization, reporting to the SVP.
The role involves close partnership with Product Managers, Engineers, Researchers, Data Scientists, and Operational Stakeholders, indicating a highly collaborative, cross-functional structure.
The Product Designer will report into the SVP, Product, Design, Data, suggesting a direct line of communication with senior leadership. Methodology:
Focus on defining user experiences that align with Oscar's mission and user needs.
Emphasis on user research and usability testing to drive informed design decisions.
Collaborative approach with cross-functional teams to drive features from discovery through delivery.
Contribution to and utilization of a design language system ("Anatomy") for consistency and scalability.
Leveraging modern workflows and AI-assisted tools for efficiency.

Company Website: http://www.hioscar.com/

📝 Enhancement Note: Oscar Health's identity as a tech-first health insurance company suggests a culture that values innovation, data-driven decision-making, and a user-centric approach. The "relentless focus on serving our members" is a key cultural driver that designers will need to embody.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a mid-to-senior level Product Designer, requiring significant experience (4+ years) and the ability to manage complex projects and stakeholders. The focus on ICHRA and enterprise tooling suggests a specialization within a critical business area.

Reporting Structure: The Product Designer reports to the SVP, Product, Design, Data. This direct reporting line to senior leadership offers visibility and the potential for significant influence on product strategy and design direction. Collaboration will be extensive with peers in Product Management, Engineering, and Data Science.

Operations Impact: The Product Designer's work directly impacts the usability and efficiency of employer-facing tools, which in turn affects how employers manage health benefits for their employees. This has a downstream effect on member experience, operational efficiency for Oscar, and the company's ability to scale its offerings like ICHRA. Success in this role contributes to revenue generation and operational excellence by simplifying complex processes.

Growth Opportunities:

Specialization: Deepen expertise in designing for complex financial and HR-related enterprise software within the health insurance domain.
Leadership: Potential to grow into a Senior Product Designer role, lead design initiatives for specific product areas, or mentor junior designers.
Skill Development: Opportunities to hone skills in AI-assisted design, advanced user research, and contributing to a mature design system.
Cross-functional Impact: Gain experience influencing product strategy and roadmap through strong collaboration and advocacy for user needs.

📝 Enhancement Note: The role's focus on a specific, complex product area (ICHRA) and reporting to an SVP indicates a high potential for growth and impact. The emphasis on autonomy and cross-functional leadership suggests a fast-paced learning environment where designers can take ownership and drive significant product outcomes.

🌐 Work Environment

Office Type: This is a fully remote position, offering the flexibility of working from home. However, the description mentions that "our approach to work may adapt over time" and "Future models could potentially involve a hybrid presence at the hub office associated with your metro area," suggesting a potential shift towards hybrid work in the future.

Office Location(s): The role is open to candidates residing in San Francisco, California. While remote, the connection to a specific metro area implies potential future office interactions or a designated hub.

Workspace Context:

The remote nature requires self-discipline and strong communication skills to maintain collaboration and productivity.
Access to modern design tools (Figma, Claude Code) and collaboration platforms is expected.
Opportunities for collaboration will primarily be virtual, through video calls, Slack, and shared design files.
The environment is likely fast-paced, typical of a tech company focused on rapid innovation and delivery.

Work Schedule: The standard 40-hour work week is implied. Remote work typically offers some flexibility in scheduling daily tasks, but core working hours will likely align with team needs for synchronous collaboration, especially across different time zones if applicable.

📝 Enhancement Note: The remote-first approach in San Francisco signals a commitment to talent acquisition beyond geographical constraints, while also acknowledging potential future shifts towards hybrid models. This requires candidates to be comfortable with remote collaboration tools and proactive communication.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: A recruiter or hiring manager will review applications and portfolios to assess fit based on experience and qualifications.
Portfolio Review & Design Challenge: Candidates will likely present their portfolio, discussing their process, design decisions, and impact. A design challenge, potentially focused on a specific problem related to ICHRA or a similar complex system, may be assigned.
Cross-functional Interviews: Interviews with Product Managers, Engineers, and potentially other Designers to assess collaboration skills, technical understanding, and design approach.
Leadership Interview: A final interview, potentially with the SVP, Product, Design, Data, to discuss strategic thinking, cultural fit, and overall alignment with Oscar Health's mission.

Portfolio Review Tips:

Highlight ICHRA/Enterprise Context: Select case studies that best demonstrate experience with complex enterprise software, data-intensive platforms, or workforce management tools, ideally with a healthcare or financial services angle.
Showcase Process & Impact: Clearly articulate your design process, from research and ideation to final delivery. Quantify the impact of your designs whenever possible (e.g., conversion improvements, time savings, user satisfaction scores).
Demonstrate Cross-functional Collaboration: Explain how you worked with product managers, engineers, and other stakeholders, highlighting your ability to drive consensus and navigate technical constraints.
Visual Storytelling: Use clear visuals, user flows, wireframes, and prototypes to tell the story of your design solutions. Explain your rationale for key design decisions.
AI Tool Integration: If possible, mention or show how AI tools were used to enhance your design process or efficiency.

Challenge Preparation:

Understand ICHRA: Research Individual Coverage Health Reimbursement Arrangements and their typical user journeys for employers and employees.
Problem-Solving Framework: Be prepared to articulate your approach to solving design problems, focusing on user needs, business goals, and technical feasibility.
Communicate Trade-offs: Be ready to discuss design trade-offs and how you prioritize features and solutions.
Articulate Design Vision: Be prepared to discuss your design philosophy and how you contribute to a cohesive and scalable design system.

📝 Enhancement Note: The emphasis on "complex enterprise software, data-intensive platforms, or workforce management tools" in the job description means portfolio case studies should lean towards these types of projects. The mention of AI tools suggests a candidate comfortable with modern workflows.

🛠 Tools & Technology Stack

Primary Tools:

Figma: Essential for wireframing, prototyping, high-fidelity design, and collaboration.
Claude Code: Explicitly mentioned as an AI-assisted tool to streamline the design-to-engineering process.
Prototyping Tools: Beyond Figma, any experience with dedicated prototyping software (e.g., InVision, Axure) is beneficial.

Analytics & Reporting:

Experience with analytics platforms (e.g., Google Analytics, Amplitude, Mixpanel) to understand user behavior and measure design impact is highly valuable, though not explicitly required.
Ability to interpret data to inform design decisions. CRM & Automation:
While not a direct requirement, familiarity with CRM systems or platforms that manage user data and workflows could be beneficial, given the enterprise software context.
Understanding of how design integrates with broader business processes and automation.

📝 Enhancement Note: The explicit mention of Figma and Claude Code highlights the expected technical proficiency. Candidates should be prepared to discuss their experience with these tools and how they leverage them to enhance design efficiency and outcomes.

👥 Team Culture & Values

Operations Values:

Member-Centricity: A core value, driven by the mission to make healthcare affordable and accessible. Designers are expected to advocate for the member and employer user.
Innovation & Technology: Oscar Health is a tech-first company, valuing forward-thinking solutions and the adoption of new tools (like AI) to improve processes.
Collaboration & Transparency: Working in cross-functional teams requires open communication, constructive feedback, and a shared commitment to project success.
Data-Driven Decisions: Leveraging research, testing, and analytics to inform design choices and measure impact.
Humility & Determination: The job description mentions "humble yet determined" as a desirable trait, suggesting a culture that values resilience, continuous learning, and a collaborative spirit.

Collaboration Style:

Cross-functional Partnership: Close working relationships with Product Managers, Engineers, Researchers, and Data Scientists are crucial.
Design Critiques: Active participation in design critiques, providing and receiving thoughtful feedback to elevate the quality of design work.
Shared Ownership: A culture where teams collectively own the success of features and products, fostering a sense of shared responsibility.
Process Improvement: Openness to iterating on workflows and methodologies to enhance efficiency and effectiveness.

📝 Enhancement Note: The "humble yet determined" trait, coupled with a focus on collaboration and data, suggests a culture that balances ambition with teamwork and a willingness to learn from both successes and failures.

⚡ Challenges & Growth Opportunities

Challenges:

Designing for Complexity: ICHRA and employer benefits management are inherently complex domains. Translating these into intuitive and scalable user experiences requires significant problem-solving skills.
Balancing Stakeholder Needs: Juggling the requirements and expectations of various stakeholders (employers, employees, brokers, internal teams) while maintaining a consistent user experience.
Navigating Technical Constraints: Delivering innovative design solutions within the realities of existing technical infrastructure and development timelines.
Driving Adoption of New Tools: Encouraging the use of new design tools and processes, such as AI-assisted tools, within the team and organization.

Learning & Development Opportunities:

Specialized Domain Expertise: Deepen knowledge in health insurance, specifically ICHRA, and enterprise software design for HR/benefits administration.
Advanced Design Skills: Opportunities to refine skills in complex user flows, data visualization, and contributing to sophisticated design systems.
AI in Design: Gain practical experience and insights into leveraging AI tools for design efficiency, workflow optimization, and potentially generative design.
Leadership and Mentorship: Potential to take on more responsibility, lead design initiatives, and mentor junior designers as the team grows.

📝 Enhancement Note: The challenges presented are typical for roles involving enterprise software in regulated industries like healthcare. The growth opportunities are tied to developing specialized domain expertise and mastering advanced design methodologies, including emerging AI applications.

💡 Interview Preparation

Strategy Questions:

"Describe a time you had to design for a complex, data-intensive platform. What were the key challenges and how did you address them?" (Focus on process, problem-solving, and outcomes.)
"How do you balance the needs of multiple stakeholders (e.g., product, engineering, business) when designing a feature? Provide an example." (Highlight collaboration, communication, and negotiation skills.)
"Walk us through a challenging design decision you made. What was the problem, your proposed solution, and the impact?" (Demonstrate critical thinking, user empathy, and ability to justify design choices.) Company & Culture Questions:
"Why are you interested in Oscar Health and specifically this Product Designer role focusing on ICHRA?" (Showcase research on Oscar's mission, the Lucie Marketplace, and your passion for healthcare innovation.)
"How do you approach user research and usability testing to ensure your designs are user-centered?" (Detail your methodology and how you translate insights into actionable design improvements.)
"How do you contribute to a design system and ensure consistency across products?" (Discuss your experience with design systems like "Anatomy" and your approach to maintaining brand integrity.) Portfolio Presentation Strategy:
Structure: Organize your portfolio around 2-3 strong case studies. For each, clearly define the problem, your role, the process, key decisions, and the final outcome/impact.
Visuals: Use high-quality visuals (wireframes, mockups, prototypes, user flows) to illustrate your design thinking.
Storytelling: Narrate your design journey, focusing on the "why" behind your decisions and the challenges you overcame.
Quantify Impact: Whenever possible, provide metrics that demonstrate the success of your designs (e.g., increased conversion, reduced errors, improved satisfaction).
Prepare for Q&A: Anticipate questions about your design choices, trade-offs, and how you collaborate with technical teams. Be ready to discuss your experience with Figma and Claude Code.

📝 Enhancement Note: Interview preparation should emphasize demonstrating an understanding of complex systems, cross-functional collaboration, and the ability to translate user needs into effective, scalable design solutions within the health insurance domain.

📌 Application Steps

To apply for this Product Designer position:

Submit your application through the Oscar Health careers portal at http://www.hioscar.com/careers/8107009?gh_jid=8107009.
Curate Your Portfolio: Select 2-3 of your most relevant case studies that showcase your experience with complex enterprise software, data-intensive platforms, or workforce management tools. Ensure they highlight your end-to-end design process, user research integration, and quantifiable impact.
Tailor Your Resume: Emphasize your 4+ years of Product/UX design experience, stakeholder management skills, and specific achievements in shipping complex web and mobile interfaces. Use keywords from the job description such as "ICHRA," "enterprise software," "Figma," and "user research."
Prepare Your Narrative: Practice articulating your design process, rationale for key decisions, and how you collaborate with cross-functional teams. Be ready to discuss your experience with AI tools like Claude Code and your understanding of the healthcare industry.
Research Oscar Health: Familiarize yourself with Oscar's mission, values, and the Lucie Marketplace. Understand the company's approach to technology and member-centricity to articulate your 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.

Product Designer, ICHRA