Product Designer, ICHRA at Oscar Health

📍 Job Overview

Job Title: Product Designer, ICHRA

Company: Oscar Health

Location: Los Angeles, California, United States

Job Type: Full-Time

Category: Product Design / UX Design

Date Posted: August 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 and the Lucie Marketplace, focusing on employer and employee needs.
Drive the end-to-end design process for complex, data-intensive enterprise software, from discovery and user research through high-fidelity delivery.
Collaborate closely with cross-functional teams, including Product Management, Engineering, Research, Data Science, and Operations, to ensure alignment and successful feature implementation.
Leverage AI-assisted tools like Claude Code alongside Figma to streamline the design-to-engineering workflow and enhance productivity.
Contribute to the evolution of Oscar's design language system, "Anatomy," ensuring consistency and brand integrity across all product experiences.

📝 Enhancement Note: This role is specifically focused on the ICHRA product suite, a complex area within health insurance that requires a deep understanding of employer benefits, employee contributions, and regulatory compliance. The emphasis on "enterprise software" and "data-intensive platforms" suggests a need for experience with intricate workflows and robust data visualization. The mention of AI tools indicates a forward-thinking approach to design processes.

📈 Primary Responsibilities

Define and design intuitive, scalable, and consistent user experiences for the ICHRA product suite and the broader Lucie Marketplace.
Conduct comprehensive user research and usability testing to gather actionable insights that inform design decisions and advocate for user needs.
Partner closely with Product Managers and Tech Leads to drive clarity around product strategy and achieve alignment on proposed design solutions.
Execute design tasks across multiple technical domains, from initial wireframing and prototyping to high-fidelity visual design and interaction specifications.
Perform design critiques and actively contribute feedback to other Product Designers within the organization, fostering a collaborative design culture.
Translate complex requirements, business goals, and research findings into simple, elegant, and user-friendly interface designs.
Ensure the Oscar brand identity and values are effectively brought to life within the product experiences.
Contribute to the development and maintenance of Oscar's design language system ("Anatomy").
Collaborate with engineering teams to ensure accurate implementation of designs and provide ongoing design support throughout the development lifecycle.
Ensure compliance with all applicable laws and regulations within the healthcare industry.

📝 Enhancement Note: The responsibilities highlight a blend of strategic product thinking and hands-on design execution. The emphasis on "defining experiences" and "advocating their needs" points to a Product Designer who can influence product direction, not just execute pixel-perfect mockups. The requirement to "become an expert on the product’s users" suggests a deep dive into the ICHRA user base.

🎓 Skills & Qualifications

Education: While no specific degree is listed, a Bachelor's degree in Design, Human-Computer Interaction (HCI), Computer Science, or a related field is often preferred for Product Designer roles. A strong portfolio can often substitute for formal education.

Experience:

4+ years of experience in Product Design, UX Design, or a closely related field.
Proven track record of designing and shipping complex web and mobile interfaces, with at least two concrete examples.
2+ years of direct experience managing and collaborating with stakeholders, including Product Managers, Engineers, and business leaders. Required Skills:
Proficiency in Product Design and UX Design methodologies.
Strong visual design skills and a keen eye for aesthetics, typography, and layout.
Expertise in using design tools such as Figma for wireframing, prototyping, and high-fidelity design.
Experience conducting user research, usability testing, and synthesizing findings into actionable insights.
Demonstrated ability to manage stakeholders effectively, understand their needs, and communicate design rationale clearly.
Ability to translate complex requirements and user needs into simple, intuitive, and visually compelling interfaces.
Understanding of design systems and experience contributing to or utilizing them (e.g., "Anatomy"). Preferred Skills:
Experience within the healthcare industry, particularly with health insurance products or benefits administration.
Proficiency with AI-assisted design tools, specifically Claude Code, to enhance design and development workflows.
Experience designing for complex enterprise software, data-intensive platforms, or workforce management tools.
Skills in storytelling techniques, such as creating animated prototypes or detailed user flow diagrams, to communicate design concepts.
Familiarity with design ethics, accessibility standards (WCAG), and their application in healthcare products.
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 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 candidates who can demonstrate tangible impact and effective communication skills, not just theoretical knowledge. The preference for healthcare experience and AI tool proficiency suggests areas where candidates can differentiate themselves.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

A curated portfolio showcasing at least 4 years of professional product design experience, with a strong emphasis on complex web and mobile interfaces.
At least two detailed case studies demonstrating the full design process for shipped products, specifically highlighting complex enterprise software, data-intensive platforms, or workforce management tools.
Clear articulation of your role and contributions within each case study, detailing problem definition, user research, design iterations, and final outcomes.
Examples of how you managed and collaborated with stakeholders throughout the design lifecycle.
Visual demonstrations of your visual design skills, UI execution, and understanding of design systems.
Evidence of user research and usability testing methodologies employed and their impact on design decisions. Process Documentation:
Case studies should clearly outline the design process followed, from initial discovery and problem framing to iterative design and final implementation.
Demonstrate how you leveraged user research and data to drive design decisions and measure success.
Showcase your ability to document workflows, user journeys, and interaction patterns effectively.
Include examples of how you collaborated with engineering and product teams to ensure successful product launches.
If applicable, include examples of how you've utilized AI-assisted tools or contributed to design systems.

📝 Enhancement Note: For a Product Designer role, the portfolio is paramount. The emphasis on "complex enterprise software" and "data-intensive platforms" means candidates should select case studies that clearly illustrate their ability to handle intricate user flows and data visualization. The requirement for "2+ concrete examples of designing and shipping" means these should be substantial, not just concept projects.

💵 Compensation & Benefits

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

Explanation: This salary range is provided directly by the company and is competitive for a Product Designer role with 4+ years of experience in a major metropolitan area like Los Angeles. Factors influencing the exact placement within this range will include the candidate's specific experience, skills, and interview performance.

Benefits:

Medical, dental, and vision insurance
Unlimited vacation program
Company equity grants
Annual performance bonuses
11 paid holidays
Paid sick time
Paid parental leave
401(k) plan participation
Life insurance
Disability insurance
Paid wellness time and reimbursements

Working Hours: Standard full-time hours (approximately 40 hours per week), with a hybrid work schedule requiring 3 days in the office per week. Thursdays are a mandatory in-office day for team meetings and events.

📝 Enhancement Note: The salary range is explicitly stated, which is a positive indicator for transparency. The benefits package is comprehensive, covering health, financial well-being, and work-life balance, which are attractive to mid-to-senior level professionals. The hybrid work arrangement is clearly defined.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance Technology (HealthTech)

Company Size: Oscar Health is a significant player in the health insurance market, utilizing a technology-first approach. Its size suggests a dynamic environment with opportunities for impact, but also a need for efficient processes and clear communication. The company is publicly traded and has grown considerably since its founding.

Founded: 2012. Oscar was founded with the vision of transforming health insurance through technology and a focus on consumer experience. This history suggests a culture that values innovation, customer-centricity, and leveraging technology to solve complex problems.

Team Structure:

The Product Design team likely operates within a larger Product, Design, and Data organization, reporting to the SVP of Product, Design, Data.
This role partners closely with Product Managers, Engineers, Researchers, Data Scientists, and Operational Stakeholders, indicating a highly cross-functional collaboration model.
The mention of "Senior Product Designer in this space" suggests a potential mentorship or team lead structure within the ICHRA product area. Methodology:
Data-driven decision-making is likely a core methodology, given the company's tech focus and the role's emphasis on research and analytics.
Agile methodologies are expected for product development, requiring designers to be adaptable and responsive to feedback.
A strong emphasis on user empathy and understanding user journeys is central to Oscar's mission and product design approach.
The use of AI-assisted tools indicates an openness to modern workflows and efficiency improvements.

Company Website: http://www.hioscar.com/careers/8106999?gh_jid=8106999

📝 Enhancement Note: Oscar Health's identity as a tech-driven health insurance company implies a culture that values innovation, user experience, and data. The specific focus on ICHRA within the "Lucie Marketplace" suggests a strategic growth area for the company.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a mid-to-senior level Product Designer. It requires a solid foundation of experience (4+ years) and the ability to manage stakeholders and complex projects independently. The candidate is expected to contribute significantly to product strategy and execution.

Reporting Structure: The Product Designer will report to the SVP, Product, Design, Data. This senior reporting line suggests visibility and potential for direct impact on high-level product decisions. The role also involves close collaboration with Product Managers and Senior Product Designers, offering opportunities for mentorship and peer learning.

Operations Impact: The Product Designer will directly influence the user experience of critical employer and employee-facing tools within the health insurance domain. Success in this role means making health plan management more accessible, understandable, and efficient for Oscar's clients, thereby contributing to the company's mission of making healthier lives affordable and accessible. This role's impact is tied to user adoption, satisfaction, and the operational efficiency of managing health benefits.

Growth Opportunities:

Skill Specialization: Opportunity to deepen expertise in designing complex enterprise software, data-intensive platforms, and specifically within the healthcare benefits administration space (ICHRA).
Leadership Potential: Potential to grow into a Senior Product Designer role, leading design initiatives for specific product areas, mentoring junior designers, and contributing more heavily to product strategy.
Cross-functional Advancement: Experience gained in stakeholder management and cross-functional collaboration can open doors to product management or other leadership roles within the product organization.
Design System Contribution: Opportunity to become a key contributor or even lead aspects of the "Anatomy" design system.

📝 Enhancement Note: The reporting structure to an SVP indicates a high-potential role with significant visibility. Growth opportunities are tied to developing specialized domain expertise and demonstrating leadership in design execution and collaboration.

🌐 Work Environment

Office Type: Hybrid work model, requiring 3 days per week in the Los Angeles office. Thursdays are a mandatory in-office day for team meetings and events.

Office Location(s): Los Angeles, California, United States. Specific details about the office environment (e.g., open plan, dedicated desks, amenities) are not provided but can be expected to be modern and conducive to collaboration for a tech company.

Workspace Context:

The hybrid model emphasizes collaboration and team cohesion, with designated in-office days for meetings, brainstorming, and in-person interaction.
The use of Figma and AI tools suggests a tech-forward workspace equipped with modern design software and hardware.
Opportunities for interaction with a diverse range of cross-functional teams (Product, Engineering, Data, Operations) will be frequent.

Work Schedule: Standard full-time work schedule, approximately 40 hours per week. The hybrid nature allows for some flexibility in structuring the three in-office days, with Thursdays being a fixed team day.

📝 Enhancement Note: The hybrid model is clearly defined, indicating a balance between in-person collaboration and remote flexibility. The focus on Thursdays for team events suggests a structured approach to fostering team connection.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: A recruiter or hiring manager will review your application and portfolio to assess initial fit.
Portfolio Review & Design Challenge: Expect a deeper dive into your portfolio, potentially including a take-home design challenge or a live design exercise focused on solving a product problem relevant to ICHRA or enterprise software. This will assess your design process, problem-solving skills, and ability to articulate your rationale.
Cross-functional Interviews: Interviews with Product Managers, Engineers, and potentially other Designers to evaluate collaboration style, technical understanding, and ability to work within a team.
Stakeholder Interview: An interview with the SVP, Product, Design, Data, or other senior leaders to discuss strategic thinking, leadership potential, and overall cultural fit.

Portfolio Review Tips:

Tailor your portfolio: Select case studies that best showcase your experience with complex enterprise software, data-intensive platforms, and user-centric design. Highlight your work on ICHRA or similar benefits administration tools if possible.
Quantify impact: For each case study, clearly articulate the problem you solved, your specific contributions, the design process you followed, and the measurable outcomes (e.g., improved user satisfaction, increased conversion rates, reduced support tickets).
Show your process: Don't just present final screens. Explain your research, ideation, iteration, and how you incorporated feedback. Use visuals like user flows, wireframes, and prototypes to illustrate your journey.
Be ready to discuss: Prepare to talk through your design decisions, the trade-offs you made, and how you navigated challenges. Be ready to explain your experience managing stakeholders and collaborating with engineering.
Highlight AI tool usage: If you have experience with AI-assisted tools like Claude Code, be prepared to discuss how you've integrated them into your workflow.

Challenge Preparation:

Understand ICHRA: Research what ICHRA is, who the users are (employers, employees, brokers), and common pain points associated with managing these plans.
Focus on Enterprise Needs: Think about the complexities of enterprise software, such as scalability, data security, administrative workflows, and integration with other systems.
Practice articulating your process: Be able to clearly and concisely explain your design thinking, from problem definition to solution.

📝 Enhancement Note: The interview process is likely multi-stage, common for design roles in larger tech companies. The emphasis on portfolio review and a potential design challenge means candidates must be well-prepared to demonstrate their practical skills and thought process. Understanding ICHRA is a key differentiator.

🛠 Tools & Technology Stack

Primary Tools:

Figma: The core design and prototyping tool for creating wireframes, mockups, and interactive prototypes. Proficiency is essential.
AI-Assisted Design Tools (e.g., Claude Code): Expected to leverage these tools for code generation, design assistance, or workflow optimization. Familiarity is a plus.

Analytics & Reporting:

Experience with analytics platforms (e.g., Google Analytics, Mixpanel, Amplitude) to understand user behavior and measure design impact is beneficial.
Ability to interpret data to inform design decisions. CRM & Automation:
While not a direct CRM role, understanding how design interfaces interact with backend systems and data management processes is important.
Familiarity with how design impacts user workflows within broader business systems. Other Potential Tools:
Prototyping tools (e.g., InVision, ProtoPie)
User research platforms (e.g., UserTesting.com, Lookback)
Collaboration tools (e.g., Slack, Jira, Confluence)
Design System tools/documentation platforms

📝 Enhancement Note: Figma is explicitly mentioned as a key tool. The inclusion of AI-assisted tools like Claude Code signals a modern design stack. While direct CRM or automation tool experience isn't listed as a requirement, understanding how design fits into these broader systems is valuable.

👥 Team Culture & Values

Operations Values:

User-Centricity: A deep commitment to understanding and serving the needs of Oscar's members and employers.
Innovation: A drive to leverage technology and new approaches (like AI) to solve complex problems in healthcare.
Collaboration: A belief that the best solutions emerge from working closely with diverse teams and perspectives.
Efficiency & Scalability: A focus on designing solutions that are not only effective but also scalable and efficient for both users and the business.
Humility & Determination: A culture that values genuine curiosity, a willingness to learn, and a persistent drive to achieve goals.

Collaboration Style:

Highly collaborative and cross-functional, requiring designers to work seamlessly with Product Managers, Engineers, Researchers, Data Scientists, and Operations.
Open to feedback and constructive critique, with a culture of peer review to elevate design quality.
Emphasis on clear communication and alignment to ensure everyone is working towards common goals.
A proactive approach to problem-solving, involving stakeholders early and often.

📝 Enhancement Note: The "humble yet determined" characteristic is a specific cultural indicator. The emphasis on collaboration with a wide range of disciplines is critical for success in this role.

⚡ Challenges & Growth Opportunities

Challenges:

Complexity of Healthcare Regulations: Navigating the intricate regulatory landscape of healthcare and health insurance (especially ICHRA) while designing user-friendly experiences.
Balancing Enterprise Needs with User Experience: Designing for complex administrative workflows for employers while ensuring an intuitive and accessible experience for employees.
Cross-functional Alignment: Ensuring consistent vision and execution across multiple departments (Product, Engineering, Data, Operations) with potentially competing priorities.
Rapidly Evolving Technology: Staying current with design tools, AI advancements, and best practices in a fast-paced tech environment.

Learning & Development Opportunities:

Domain Expertise: Deepen knowledge in health insurance, specifically ICHRA, and benefits administration.
Advanced Design Techniques: Opportunity to refine skills in complex enterprise design, data visualization, and potentially AI-assisted design workflows.
Leadership & Mentorship: Potential to grow into leadership roles, mentor junior designers, and influence product strategy.
Industry Exposure: Exposure to the innovative side of health insurance and technology through Oscar's unique approach.

📝 Enhancement Note: The challenges are inherent to the healthcare tech industry and the nature of enterprise software. The growth opportunities are tied to both domain specialization and leadership development.

💡 Interview Preparation

Strategy Questions:

"Describe your process for designing a complex, data-intensive enterprise feature from discovery to delivery. Walk us through a specific example." (Focus on your systematic approach, research methods, and iteration process.)
"How do you balance the needs of different stakeholders (e.g., Product Managers, Engineers, Business Leaders) when designing a feature? Provide an example of a time you managed competing priorities." (Highlight your communication, negotiation, and alignment skills.)
"Tell us about a time you had to design within significant technical constraints. How did you approach the problem, and what was the outcome?" (Showcase your problem-solving and adaptability.) 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 contribute to a collaborative design team? Describe your experience with design critiques and feedback." (Emphasize your team-player attitude and openness to feedback.)
"How do you ensure your designs are accessible and inclusive, especially in a sensitive area like healthcare?" (Discuss your understanding of accessibility standards and ethical design.) Portfolio Presentation Strategy:
Structure: Organize your presentation logically, starting with the business/user problem, your role, the process, your solutions, and the outcomes.
Storytelling: Frame each case study as a narrative. Explain the "why" behind your decisions.
Visuals: Use high-quality visuals – wireframes, user flows, prototypes, final UI – to illustrate your points. Ensure clarity and readability.
Metrics: Quantify your impact whenever possible using relevant metrics. If direct metrics aren't available, discuss how you would measure success.
AI Integration: Be prepared to discuss any use of AI tools in your workflow and their benefits.
Conciseness: Be mindful of time. Practice your presentation to ensure it's engaging and fits within the allotted timeframe.

📝 Enhancement Note: Preparation should focus on demonstrating a robust design process, strong stakeholder management, and an understanding of the unique challenges in the healthcare enterprise software space. Emphasizing quantifiable results and clear communication 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.
Tailor your Resume: Highlight keywords from the job description, such as "Product Design," "UX Design," "ICHRA," "enterprise software," "data-intensive platforms," "stakeholder management," and "Figma." Quantify your achievements with specific numbers where possible.
Curate Your Portfolio: Select 2-3 of your strongest case studies that best align with the requirements for designing complex enterprise software and ideally demonstrate experience with data-heavy interfaces or B2B/workforce management tools. Ensure your portfolio clearly articulates your role, process, and impact.
Prepare Your Portfolio Presentation: Practice walking through your selected case studies, focusing on storytelling, articulating your design decisions, and demonstrating your ability to collaborate. Be ready to discuss your experience with user research, stakeholder management, and any use of AI tools.
Research Oscar Health: Familiarize yourself with Oscar's mission, values, products (especially the Lucie Marketplace and ICHRA), and recent company news to demonstrate genuine 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.

Product Designer, ICHRA