Product Designer, ICHRA at Oscar Health

📍 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: 2026-08-14

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

Remote Status: Hybrid

🚀 Role Summary

Design and deliver intuitive user experiences for Oscar's ICHRA (Individual Coverage Health Reimbursement Arrangement) platform, a key component of the Lucie Marketplace.
Collaborate closely with cross-functional teams, including Product Managers, Engineers, Researchers, Data Scientists, and Operational Stakeholders, to guide features from initial discovery through to high-fidelity delivery.
Leverage AI-assisted design tools like Claude Code alongside Figma to streamline the design-to-engineering process, enhancing execution speed and design quality.
Become an expert on user needs and pain points within the ICHRA ecosystem, advocating for user-centric solutions across the organization.
Contribute to the evolution of Oscar's Design Language System (Anatomy) and ensure a consistent, scalable, and user-friendly experience across the entire Lucie suite.

📝 Enhancement Note: While the title is "Product Designer," the responsibilities and required experience lean towards a mid-senior level designer with a strong emphasis on complex enterprise software, data-intensive platforms, and workforce management tools, aligning with a more specialized UX/Product Design role rather than a generalist. The focus on ICHRA and the Lucie Marketplace indicates a strategic product design opportunity within the health insurance tech sector.

📈 Primary Responsibilities

Define and meticulously craft user experiences that enable a wide array of use cases for Oscar's ICHRA platform, directly contributing to the mission of making healthier lives affordable and accessible.
Deeply understand the target users of the ICHRA product and their complete journey, acting as a primary advocate for their needs and pain points within the broader organizational context.
Take full ownership of the design process for assigned features, working in close partnership with product managers, tech leads, engineers, data scientists, and business stakeholders to ensure strategic clarity and alignment on proposed solutions.
Actively participate in design critiques, providing thoughtful feedback and contributing to the overall advancement of the design team's collective output and best practices.
Conduct rigorous user research and usability testing, with a sharp focus on generating actionable insights that inform and drive critical design decisions.
Create visually compelling and user-friendly interfaces, ensuring a cohesive brand experience and contributing to the ongoing development and application of Oscar's Design Language System, "Anatomy."
Ensure all product designs are compliant with applicable laws and regulations within the healthcare industry.
Execute other assigned duties as necessary to support product design initiatives and team objectives.

📝 Enhancement Note: The responsibilities highlight a hands-on design role with significant ownership and cross-functional collaboration. The emphasis on user research, usability testing, and contributing to a design system indicates a need for a designer proficient in both strategic thinking and detailed execution. The inclusion of compliance suggests an awareness of regulatory requirements in the healthcare space.

🎓 Skills & Qualifications

Education:

Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field, or equivalent practical experience. Experience:
4+ years of professional experience in Product Design, UX Design, or a closely related field, with a demonstrated ability to ship complex digital products.
Proven experience in managing and influencing stakeholders, ensuring design solutions align with business objectives and user needs.
Demonstrable experience navigating technical constraints and collaborating effectively with engineering teams to deliver robust design solutions. Required Skills:
Expertise in user-centered design principles and methodologies.
Proficiency in modern design and prototyping tools, with a strong emphasis on Figma.
Experience conducting user research, usability testing, and synthesizing findings into actionable design improvements.
Demonstrated ability to design and ship complex web and mobile interfaces, with at least two concrete examples of successful product launches.
Strong stakeholder management skills, with the ability to communicate design rationale and build consensus.
Excellent visual design skills, with an understanding of design systems and brand consistency. Preferred Skills:
Experience within the healthcare industry, particularly with health insurance products or platforms.
Familiarity with AI-assisted design tools such as Claude Code for enhancing design workflows.
Experience in designing for enterprise software, data-intensive platforms, or workforce management tools.
Proficiency in creating animated prototypes or detailed user flow diagrams to effectively communicate design concepts.
A strong interest in design ethics, accessibility standards, and their application within the healthcare context.
Evidence of contributing to internal tools, system workflows, or power-user interfaces.
A genuinely inquisitive, humble, and determined approach to problem-solving and design challenges.

📝 Enhancement Note: The requirements emphasize a blend of foundational UX/UI skills with specific experience in complex enterprise environments and stakeholder management. The preference for healthcare experience, AI tool familiarity, and design ethics suggests a desire for a candidate who can bring specialized knowledge and a forward-thinking approach to a regulated industry.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

Showcase at least two distinct projects demonstrating the design and successful shipment of complex web and/or mobile interfaces.
Highlight instances where you managed stakeholders directly, detailing your approach to communication, feedback integration, and alignment.
Provide examples of how you navigated technical constraints to deliver effective design solutions, illustrating your problem-solving process.
Include case studies that detail your involvement in user research and usability testing, along with the insights gained and their impact on design decisions.
Demonstrate your understanding and application of design systems, ideally showcasing contributions to or utilization of a design language system like "Anatomy." Process Documentation:
Clearly articulate your design process from initial concept and user research through to final delivery and iteration.
Detail your approach to cross-functional collaboration, illustrating how you partner with product managers, engineers, and other stakeholders.
Explain your methods for integrating user feedback and research findings into iterative design improvements.
Illustrate your workflow for translating complex requirements, goals, and research data into simple, intuitive user interfaces.

📝 Enhancement Note: The portfolio requirements are crucial for this role, demanding concrete evidence of past work, particularly in complex environments. Candidates should be prepared to articulate their design process, stakeholder management strategies, and how they translate user needs and technical realities into successful product features.

💵 Compensation & Benefits

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

Benefits:

Comprehensive Medical, Dental, and Vision benefits.
11 paid holidays, paid sick time, and paid parental leave.
401(k) plan participation.
Life and disability insurance.
Paid wellness time and wellness reimbursements.
Participation in Oscar's unlimited vacation program.
Company equity grants.
Annual performance bonuses. Working Hours:
Standard full-time hours, typically 40 hours per week.
Hybrid work schedule requiring 3 days in the New York City office per week, with Thursdays designated as a mandatory in-office day for team meetings and events.

📝 Enhancement Note: The salary range provided is competitive for a Product Designer role in New York City, especially for a hybrid position with significant responsibilities. The extensive benefits package, including unlimited vacation and equity, reflects a comprehensive total compensation approach. The hybrid requirement with specific in-office days is a key detail for candidates assessing work-life integration.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance Technology (HealthTech)

Company Size: 1,001-5,000 employees (as per LinkedIn Data)

Founded: 2012

Team Structure:

The Product Design team is part of a larger Product, Design, Data organization, reporting to the SVP, Product, Design, Data.
This role involves close collaboration with Product Managers, Engineers, Researchers, Data Scientists, and Operational Stakeholders, indicating a highly cross-functional and integrated team environment.
The specific ICHRA focus suggests a specialized sub-team or dedicated effort within the broader Product Design function. Methodology:
Oscar emphasizes a technology-driven approach to healthcare, leveraging a full-stack platform to enhance member experience.
The design team operates with a focus on user-centricity, data-driven decision-making, and a commitment to shipping impactful features.
Collaboration is key, with an expectation of feedback exchange during critiques and contributions to a shared design language system.
The integration of AI-assisted tools like Claude Code points to a forward-thinking adoption of technology to optimize workflows.

Company Website: http://www.hioscar.com/careers/8103430?gh_jid=8103430

📝 Enhancement Note: Oscar Health positions itself as a modern, tech-forward health insurance company. The culture likely values innovation, collaboration, and a strong user focus. The company's mission to make healthcare affordable and accessible is a core driver, and employees are expected to contribute to this goal through their work. The size of the company suggests a balance between established processes and the agility of a growing organization.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a mid-to-senior level within Product Design. It requires significant autonomy in managing design processes and stakeholder relationships, moving beyond junior execution tasks to strategic contributions. The focus on specific product areas like ICHRA and the Lucie Marketplace indicates opportunities for specialization and deep domain expertise.

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 strategic product decisions. Collaboration will extend across various departments, fostering broad organizational understanding.

Operations Impact: The Product Designer's work directly impacts Oscar's ability to serve employers and their employees through the Lucie Marketplace. By designing intuitive ICHRA tools, the role contributes to increased adoption, improved user satisfaction, and operational efficiency for businesses managing health benefits. This has a downstream effect on Oscar's market competitiveness and revenue growth.

Growth Opportunities:

Specialization: Deepen expertise in health insurance products, particularly ICHRA and employer benefits administration, becoming a subject matter expert.
Leadership: Progress to Senior Product Designer roles, potentially leading design initiatives for specific product areas or mentoring junior designers.
Skill Development: Gain experience with cutting-edge design tools (including AI-assisted ones), advanced user research techniques, and complex enterprise software design challenges.
Cross-Functional Exposure: Broaden understanding of product management, engineering, data science, and operational intricacies within the health insurance sector.

📝 Enhancement Note: This role offers a clear path for career progression within a specialized area of health tech. The opportunity to work on complex, impactful products with senior leadership visibility provides a strong foundation for future growth in product design leadership or specialized domain expertise.

🌐 Work Environment

Office Type: Hybrid work model based in Oscar Health's New York City office.

Office Location(s): New York City, New York, United States. Specific office address is not provided, but candidates should expect a modern, collaborative workspace typical of a tech company.

Workspace Context:

The hybrid model requires 3 days per week in the office, with a mandatory presence on Thursdays for team meetings and events, fostering in-person collaboration and team cohesion.
The office environment is expected to be conducive to collaborative design work, with access to necessary tools and technology.
Opportunities for interaction with a diverse range of colleagues across product, engineering, data, and operations teams will be frequent. Work Schedule:
Standard full-time working hours (approximately 40 hours per week).
The hybrid schedule offers some flexibility in choosing which days to work from the office, beyond the mandatory Thursday. This allows for balancing focused individual work with collaborative team engagement.

📝 Enhancement Note: The hybrid work environment is designed to balance the benefits of in-person collaboration and team building with the flexibility of remote work. Candidates should be prepared for a structured hybrid approach that prioritizes key in-office days for team synergy.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: A review of your application, resume, and portfolio to assess foundational skills and experience.
Hiring Manager Interview: Discussion focused on your experience, design philosophy, and alignment with the role's requirements, particularly regarding complex enterprise software and stakeholder management.
Portfolio Presentation & Design Challenge: A session where you present your portfolio, showcasing specific case studies relevant to the role (e.g., complex interfaces, stakeholder management). You may also be given a design challenge to assess your problem-solving skills and design process in real-time or as a take-home assignment.
Cross-Functional Interviews: Meetings with Product Managers, Engineers, or other key stakeholders to evaluate collaboration style, communication skills, and technical understanding.
Final Round/Executive Interview: A discussion with senior leadership (potentially the SVP) to assess strategic thinking, cultural fit, and overall potential impact.

Portfolio Review Tips:

Curate Selectively: Focus on 2-3 projects that best showcase your experience with complex web/mobile interfaces, enterprise software, and stakeholder management.
Tell a Story: For each project, clearly articulate the problem, your role, the design process (research, ideation, iteration), the solutions you implemented, and the measurable outcomes or impact.
Highlight ICHRA/Enterprise Relevance: If possible, tailor examples to demonstrate experience with data-intensive platforms, workforce management tools, or complex business logic.
Showcase Collaboration: Explicitly describe how you worked with product managers, engineers, and other stakeholders, including how you managed feedback and resolved disagreements.
Visual Clarity: Ensure your portfolio is well-organized, visually appealing, and easy to navigate. Use high-fidelity mockups and, if possible, interactive prototypes or user flow diagrams.

Challenge Preparation:

Understand the Context: If given a design challenge, thoroughly analyze the prompt, identify the core problem, and understand the target users and business goals.
Process Over Perfection: Focus on demonstrating a structured design process, clear decision-making, and thoughtful consideration of trade-offs, rather than delivering a perfectly polished final UI.
Articulate Rationale: Be prepared to explain every design decision you make, linking it back to user needs, business objectives, or technical considerations.
Time Management: Allocate your time effectively across research, ideation, design, and preparation for presentation.

📝 Enhancement Note: The interview process is designed to thoroughly evaluate a candidate's design skills, process, collaboration abilities, and strategic thinking. A strong, well-curated portfolio is paramount, and candidates should be prepared to articulate their contributions and decision-making processes in detail.

🛠 Tools & Technology Stack

Primary Tools:

Figma: The core tool for UI design, prototyping, and collaboration. Proficiency is essential for creating high-fidelity designs and interactive prototypes.
Claude Code: Mentioned as an AI-assisted tool to streamline the design-to-engineering process. Familiarity or a willingness to learn and leverage AI in design workflows is advantageous.
Prototyping Tools: Beyond Figma's capabilities, familiarity with other advanced prototyping tools (e.g., Principle, Framer) might be beneficial for complex animations or user flows.

Analytics & Reporting:

While not explicitly listed as a designer's primary tool, understanding how to interpret data from analytics platforms (e.g., Amplitude, Google Analytics) to inform design decisions is a plus.
Experience with data visualization tools or understanding how designs will be represented in dashboards would be valuable. CRM & Automation:
While not directly used by designers, an understanding of how CRM systems (e.g., Salesforce) and automation platforms (e.g., Marketo, HubSpot) impact user workflows and data management can provide valuable context for enterprise design.

📝 Enhancement Note: The technology stack emphasizes modern design tools, particularly Figma, and highlights an openness to integrating AI into the design workflow. Designers should be comfortable with digital collaboration platforms and possess a strong understanding of how their designs integrate into broader software development and data management ecosystems.

👥 Team Culture & Values

Operations Values:

User-Centricity: A deep commitment to understanding and advocating for user needs, ensuring that designs solve real problems and provide exceptional experiences.
Collaboration: A strong emphasis on working effectively with cross-functional teams, fostering open communication, and valuing diverse perspectives to achieve shared goals.
Innovation & Efficiency: Encouraging the exploration of new ideas and technologies (like AI-assisted tools) to improve processes and deliver impactful solutions more effectively.
Impact-Driven: A focus on designing products that directly contribute to Oscar's mission of making healthcare affordable and accessible, with an understanding of how design influences business outcomes.
Continuous Improvement: A culture that supports learning, feedback, and iteration, both in design practices and product development.

Collaboration Style:

Cross-functional Integration: Designers are expected to be integral members of product teams, working hand-in-hand with Product Managers, Engineers, and Data Scientists throughout the entire product lifecycle.
Feedback Culture: Active participation in design critiques and providing constructive feedback to peers is encouraged, fostering a collective drive for design excellence.
Transparency: Open communication about design decisions, challenges, and trade-offs is valued to ensure alignment across teams.
Data-Informed: While creative, design decisions should be informed by user research, usability testing, and product analytics, demonstrating a balanced approach.

📝 Enhancement Note: Oscar Health appears to cultivate a culture that values both individual contribution and collective success, driven by a strong mission. The emphasis on user empathy, data-informed decisions, and collaborative problem-solving is key for candidates to align with.

⚡ Challenges & Growth Opportunities

Challenges:

Navigating Healthcare Complexity: The healthcare industry is inherently complex, with unique regulatory requirements (HIPAA, compliance), diverse user needs (employers, employees, brokers), and intricate data structures. Designing for ICHRA within this landscape requires careful attention to detail and a thorough understanding of the domain.
Balancing Enterprise Needs with User Experience: Designing for employers often involves complex administrative tasks and data management. The challenge lies in creating powerful yet intuitive tools that cater to both sophisticated business requirements and the end-user experience.
Cross-Functional Alignment: Ensuring consistent vision and execution across multiple departments (Product, Engineering, Data, Operations, Legal) requires strong communication and negotiation skills to keep everyone aligned on design goals and priorities.
Scalability and Consistency: As the Lucie Marketplace grows, maintaining a consistent and scalable design language system across various product areas (including ICHRA, broker platforms, and consumer marketplaces) presents an ongoing design challenge.

Learning & Development Opportunities:

Domain Expertise: Develop deep knowledge of ICHRA, employer benefits administration, and the broader health insurance ecosystem.
Advanced Design Skills: Gain proficiency in leveraging AI-assisted design tools and advanced prototyping techniques for complex enterprise applications.
Strategic Product Influence: Contribute to product strategy discussions and influence the roadmap based on user insights and design thinking.
Cross-Functional Leadership: Hone skills in stakeholder management, communication, and influencing across diverse teams, preparing for potential leadership roles.
Design System Contribution: Play a role in evolving and expanding a mature design system ("Anatomy") for a growing tech company.

📝 Enhancement Note: The role presents significant opportunities for professional growth by tackling complex challenges within a dynamic industry. Candidates who embrace these challenges and actively pursue learning will find ample room for development.

💡 Interview Preparation

Strategy Questions:

"Describe a time you had to design for a complex, data-intensive platform. What were the main challenges, and how did you approach them?" (Focus on process, stakeholder management, and problem-solving.)
"How do you ensure your designs are both user-friendly and meet stringent business/regulatory requirements in a domain like healthcare?" (Highlight your understanding of trade-offs and user advocacy.)
"Walk us through your process for translating user research insights into actionable design solutions for a new feature." (Emphasize your research synthesis and ideation skills.)
"How do you collaborate with product managers and engineers to ensure your designs are technically feasible and aligned with product strategy?" (Showcase your cross-functional partnership approach.) Company & Culture Questions:
"What interests you about Oscar Health and our mission to make healthcare more affordable and accessible?" (Research Oscar's values, recent news, and connect it to your own motivations.)
"How do you see your role contributing to the evolution of the Lucie Marketplace and the ICHRA experience?" (Demonstrate an understanding of the product's strategic importance.)
"Describe a situation where you had to manage conflicting stakeholder feedback. How did you navigate it?" (Focus on communication, negotiation, and finding common ground.) Portfolio Presentation Strategy:
Structure Your Narrative: For each case study, clearly outline the problem, your specific role and contributions, the design process (research, ideation, prototyping, testing), key decisions made, and the final outcome/impact.
Quantify Impact: Where possible, use metrics or user feedback to demonstrate the success of your designs. If direct metrics aren't available, discuss anticipated impact or qualitative improvements.
Highlight Collaboration: Explicitly mention how you partnered with product managers, engineers, and other stakeholders. Show examples of how you incorporated their feedback or navigated technical constraints.
Showcase Visuals: Use high-quality mockups, wireframes, user flows, and prototypes. If you have animated prototypes or user flow diagrams, be ready to present them.
Be Ready for Deep Dives: Anticipate detailed questions about your design choices, the tools you used, and the challenges you faced.

📝 Enhancement Note: Interview preparation should focus on demonstrating a robust design process, strong collaborative skills, and a clear understanding of how design impacts business objectives, especially within the complex healthcare domain. The portfolio presentation is a critical component; treat it as a strategic storytelling opportunity.

📌 Application Steps

To apply for this Product Designer position at Oscar Health:

Submit your application through the provided link on the Oscar Health careers page.
Portfolio Customization: Ensure your portfolio prominently features 2-3 of your strongest projects that align with the requirements for designing complex web/mobile interfaces, enterprise software, and stakeholder management. Tailor your case studies to highlight your process and impact.
Resume Optimization: Update your resume to clearly articulate your 4+ years of Product/UX Design experience, emphasizing achievements related to shipping complex products and managing stakeholders. Integrate keywords from the job description naturally.
Interview Preparation: Practice presenting your portfolio case studies, focusing on storytelling, articulating your design process, and highlighting your collaborative approach. Prepare to discuss your experience with user research, stakeholder management, and navigating technical constraints.
Company Research: Thoroughly research Oscar Health's mission, values, and the Lucie Marketplace. Understand the significance of ICHRA and how your design contributions can support the company's goals and foster a positive user experience.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions tailored for a Product Design role. All details should be verified directly with the hiring organization before making application decisions.

Product Designer, ICHRA