Product Designer, Marketplace at Oscar Health

📍 Job Overview

Job Title: Product Designer, Marketplace

Company: Oscar Health

Location: Los Angeles, California, United States

Job Type: Full-Time

Category: Product Design / UX Design

Date Posted: 2026-06-04T02:32:52

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

Remote Status: Hybrid

🚀 Role Summary

Design and deliver user-centric experiences for Oscar Health's innovative Lucie Health Marketplace, a critical platform for consumers and brokers shopping for healthcare plans.
Drive the end-to-end design process for complex web and mobile interfaces, focusing on intake systems, enrollment platforms, and CRM tooling.
Collaborate closely with cross-functional teams, including Product Management, Engineering, Research, Data, and Operations, to translate user needs into intuitive and scalable product solutions.
Leverage modern design workflows, including AI-assisted tools like Claude Code, to enhance design efficiency and accelerate the design-to-engineering handoff.
Contribute to a high-performing product design team by maintaining a strong craft, upholding design system standards, and advocating for user empathy throughout the product lifecycle.

📝 Enhancement Note: This role is specifically focused on designing the user experience for a healthcare marketplace, with a significant emphasis on the broker and consumer journeys for plan evaluation and enrollment. The mention of ICHRA tooling and CRM indicates a need for designing complex data management and workflow systems within a regulated industry. The requirement for AI-assisted tools suggests a forward-thinking design environment that embraces efficiency and innovation.

📈 Primary Responsibilities

Execute the full product design lifecycle, from discovery and research through high-fidelity delivery, for features within the Lucie Health Marketplace and related product areas.
Develop a profound understanding of broker and consumer needs within the healthcare insurance landscape to inform product strategy and design solutions.
Collaborate extensively with Product Managers to define product requirements, user stories, and feature specifications, ensuring alignment with business objectives.
Partner with Engineers to ensure seamless implementation of designs, providing detailed specifications, assets, and support throughout the development sprints.
Conduct hypothesis-driven research, including user interviews, usability testing, and A/B experiments, to gather actionable insights and iterate on designs.
Design and maintain scalable and intuitive user interfaces and workflows for complex systems such as broker enrollment platforms, consumer marketplaces, and ICHRA tooling.
Contribute to and uphold the integrity of Oscar Health's design systems, ensuring consistency, accessibility, and a strong brand translation across all product experiences.
Translate user needs and business requirements into simple, usable, and elegant UI designs, utilizing wireframes, mockups, prototypes, and user flow diagrams.
Proactively manage stakeholder expectations and communication, providing clear rationale for design decisions and incorporating feedback effectively.
Ensure designs comply with all applicable healthcare industry regulations and accessibility standards.

📝 Enhancement Note: The emphasis on "complex intake systems, enrollment platforms, or CRM tooling" points to a need for designing robust, data-heavy interfaces that manage sensitive information and guide users through multi-step processes. The role requires not just visual appeal but also functional excellence in managing user journeys for critical financial and health decisions.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field is often preferred for roles of this nature, demonstrating a foundational understanding of design principles and user-centered methodologies.

Experience: 4+ years of experience in Product Design, UX Design, or a closely related field, with a demonstrable history of designing and shipping complex web and mobile interfaces.

Required Skills:

Product Design & UX Expertise: Proven ability to lead and execute the entire product design process, from conceptualization to delivery, for complex digital products.
Interface Design: Strong command of visual design principles, interaction design patterns, and the ability to create high-fidelity mockups and prototypes.
Complex System Design: Experience designing intricate intake systems, enrollment platforms, or CRM tooling that manage significant data and guide users through multi-step processes.
Stakeholder Management: Minimum of 2 years of direct experience managing and influencing stakeholders across various departments (Product, Engineering, Marketing, etc.).
User Research & Testing: Proficiency in conducting user research, usability testing, and translating research findings into actionable design improvements.
Design Systems: Experience working with and contributing to design systems to ensure brand consistency and scalable design solutions.
Prototyping Tools: Expertise in industry-standard design and prototyping tools such as Figma.
Cross-functional Collaboration: Demonstrated ability to work effectively in a collaborative, team-oriented environment with Product Managers, Engineers, and other stakeholders.
Problem-Solving: Ability to break down complex problems, analyze requirements, and develop user-centered solutions.

Preferred Skills:

Healthcare Industry Experience: Prior experience designing within the healthcare sector, understanding its unique challenges and regulatory environment.
Storytelling & Visualization: Proficiency in creating animated prototypes, user flow diagrams, and other visual aids to effectively communicate design concepts and user journeys.
Design Ethics & Accessibility: A strong understanding of and commitment to design ethics, accessibility standards (WCAG), and inclusive design practices, particularly relevant in healthcare.
AI-Assisted Design Tools: Familiarity and comfort using AI tools (e.g., Claude Code) to enhance design workflows and accelerate development.
Agile Methodologies: Experience working within Agile or Lean development frameworks.
Data Analysis: Ability to interpret data and analytics to inform design decisions and measure impact.
Brand Translation: Skill in translating a brand's identity and voice into cohesive and compelling product experiences.

📝 Enhancement Note: The "2+ concrete examples of designing and shipping complex web and mobile interfaces" requirement, coupled with "2+ years managing stakeholders directly," suggests a need for candidates who can demonstrate tangible impact and navigate organizational dynamics. The preference for healthcare experience and familiarity with design ethics/accessibility is critical given the industry and the nature of the product.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

Demonstrate Complex System Design: Showcase at least two detailed case studies of designing and shipping complex web and mobile interfaces, ideally involving intake systems, enrollment platforms, or CRM tooling.
Highlight User-Centric Process: Clearly articulate your design process, emphasizing user research, problem definition, ideation, prototyping, testing, and iteration.
Showcase Stakeholder Management: Provide evidence of how you managed and influenced stakeholders, including examples of presenting design rationale and incorporating feedback.
Illustrate Cross-Functional Collaboration: Detail your collaboration with product managers, engineers, and other teams, showing how you contributed to shared goals.
Visual Design Excellence: Present high-fidelity mockups and interactive prototypes that demonstrate strong visual design craft, interaction design, and adherence to design principles.
Impact & Results: Quantify the impact of your design work where possible, using metrics related to user engagement, conversion rates, task completion, or efficiency improvements.

Process Documentation:

Workflow Design: Include examples of how you've mapped out complex user workflows and identified opportunities for simplification and optimization.
System Implementation: Show how your designs have been translated into functional systems, detailing any contributions to design specifications or developer handoffs.
Performance Analysis: If possible, demonstrate how you've used data or user feedback to analyze the performance of your designs post-launch and identify areas for further improvement.

📝 Enhancement Note: Candidates should prepare to walk through their portfolio projects in detail, explaining the challenges, their approach, the trade-offs made, and the outcomes. For this role, demonstrating an understanding of user flow for complex processes like enrollment or data management within a regulated industry will be key.

💵 Compensation & Benefits

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

Benefits:

Medical, Dental, and Vision Insurance
11 Paid Holidays
Paid Sick Time
Paid Parental Leave
401(k) Plan participation
Life Insurance
Disability Insurance
Unlimited Vacation Program
Company Equity Grants
Annual Performance Bonuses
Paid Wellness Time and Reimbursements

Working Hours: Full-time, typically 40 hours per week, with flexibility expected around project deadlines and team needs.

📝 Enhancement Note: The provided salary range is competitive for a mid-level Product Designer role in a major metropolitan area like Los Angeles, especially within the tech and healthcare sectors. The comprehensive benefits package, including unlimited vacation and equity, suggests a strong emphasis on employee well-being and long-term commitment.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology / Health Insurance. Oscar Health is a disruptor in the health insurance market, leveraging technology to create a more member-centric experience.

Company Size: Oscar Health is a significant player in the health insurance tech space, indicating a dynamic environment with established processes but also room for innovation and growth.

Founded: 2012. This founding year suggests a company that has moved beyond its startup phase and has established a mature operational framework while still maintaining a focus on innovation.

Team Structure:

Product Design Team: The Product Designer will report to the Sr. Director, Product Design, and will work closely with a Senior Product Designer focused on the Lucie Marketplace.
Cross-functional Collaboration: The role involves deep collaboration with Product Managers, Engineers, Researchers, Data Analysts, Marketers, Brand Designers, and Operational Stakeholders.
Focus Areas: The team is organized around specific product areas, with this role concentrating on the Lucie Health Marketplace, with a primary focus on the broker experience, but also contributing to consumer and ICHRA tooling.

Methodology:

User-Centric Design: A strong emphasis on understanding user needs through research and empathy to drive product strategy and solutions.
Hypothesis-Driven Development: Utilizing research, prototyping, and experimentation to validate ideas and gather actionable insights.
Agile & Iterative: Working within a modern workflow that likely involves agile development cycles, continuous iteration, and a focus on shipping features.
Data-Informed Decisions: Collaborating with data teams to leverage analytics for design validation and improvement.
AI-Assisted Design: Embracing AI tools to enhance productivity and streamline workflows.

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

📝 Enhancement Note: Oscar Health's mission to "change health care" implies a culture that values innovation, user advocacy, and a proactive approach to problem-solving within a complex industry. The hybrid work model and comprehensive benefits speak to an employee-focused culture.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Product Designer with 4+ years of experience, indicating a mid-level to senior individual contributor role. The focus on designing complex systems and managing stakeholders suggests a trajectory towards greater autonomy and ownership.

Reporting Structure: The Product Designer will report to the Sr. Director, Product Design, and work closely with a Senior Product Designer. This structure provides mentorship and clear direction while allowing for independent contribution.

Operations Impact: The Product Designer will directly influence the success of the Lucie Health Marketplace by designing the core user experiences for brokers and consumers. Their work will directly impact user acquisition, enrollment rates, and overall user satisfaction, contributing significantly to Oscar Health's business objectives in the individual and small group markets.

Growth Opportunities:

Specialization: Deepen expertise in healthcare technology, marketplace design, or complex B2B/B2C platforms.
Leadership: Potential to grow into a Senior Product Designer role, mentoring junior designers, leading design initiatives, and contributing more significantly to product strategy.
Cross-Functional Skill Development: Gain deeper insights into product management, engineering workflows, and operational challenges within the healthcare industry.
Impactful Projects: Opportunity to work on high-visibility projects that have a tangible impact on how people access and manage their healthcare.
Continuous Learning: Access to resources and a culture that supports learning about new design tools, methodologies, and industry trends, including AI in design.

📝 Enhancement Note: The role offers a clear path for growth within Oscar Health's product design function, either through specialization in a critical area like healthcare marketplaces or by moving into more senior leadership and strategic roles. The emphasis on shipping complex features suggests opportunities to build a strong portfolio of impactful work.

🌐 Work Environment

Office Type: Hybrid work model, requiring 3 days per week in the Los Angeles (Marina del Rey) office. Thursdays are a designated in-office team day.

Office Location(s): Marina del Rey, Los Angeles, California. This location offers a vibrant tech and creative hub environment.

Workspace Context:

Collaborative Hub: The office environment is designed to foster collaboration, with designated team days for in-person interaction, workshops, and team-building events.
Tech-Forward: Employees will have access to modern design tools and technologies, including Figma and potentially AI-assisted design software.
Cross-functional Proximity: Being in the office facilitates closer working relationships with product managers, engineers, and other cross-functional partners.
Flexible Arrangement: While requiring office presence, the hybrid model offers flexibility for remote work on other days, balancing collaboration with individual focus time.

Work Schedule: Standard full-time hours (approximately 40 hours/week), with flexibility expected to meet project demands. The hybrid schedule allows for structured in-office collaboration and focused remote work.

📝 Enhancement Note: The hybrid model indicates a belief in balancing the benefits of in-person collaboration with the flexibility of remote work. For a designer, this means opportunities to engage directly with teams and stakeholders while also having dedicated time for deep work and focused design execution.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: A recruiter or hiring manager will review your application and resume, likely followed by a brief introductory call to assess basic qualifications and cultural fit.
Portfolio Review & Discussion: Expect a session where you present your portfolio, walking through 2-3 key projects. This is where you'll demonstrate your design process, problem-solving skills, and impact. Be prepared to discuss your role, challenges, and outcomes.
Design Challenge/Exercise: You may be given a take-home design exercise or a live design challenge focused on a relevant problem area. This assesses your practical design skills, strategic thinking, and ability to work within constraints.
Cross-functional Interviews: Interviews with Product Managers, Engineers, and potentially other designers or stakeholders to assess collaboration style, technical understanding, and communication skills.
Hiring Manager/Director Interview: A final interview with the Sr. Director, Product Design, to discuss your overall fit, career aspirations, and how you align with the team's vision and Oscar Health's values.

Portfolio Review Tips:

Curate Strategically: Select projects that best demonstrate your experience with complex systems, intake/enrollment/CRM design, stakeholder management, and the full design lifecycle.
Tell a Story: For each project, clearly articulate the problem, your role, the process you followed, the challenges you faced, the solutions you designed, and the impact of your work. Use visuals effectively.
Quantify Impact: Wherever possible, use data and metrics to demonstrate the success of your designs (e.g., increased conversion, reduced error rates, improved user satisfaction).
Highlight Process: Show your thinking – sketches, wireframes, user flows, research insights, iteration rationale. This is crucial for assessing your problem-solving approach.
Focus on Broker Experience: Given the role's emphasis, ensure at least one case study highlights experience with B2B or complex workflow design that could be analogous to a broker platform.
Be Ready for AI Discussion: Be prepared to discuss your familiarity with AI tools in design and how you might leverage them.

Challenge Preparation:

Understand the Context: If given a take-home challenge, thoroughly understand the problem statement and the target users (brokers/consumers in healthcare).
Define Scope: Clearly define the scope of your solution within the given timeframe. It's better to solve a specific problem well than to tackle too much superficially.
Show Your Process: Document your thinking, even if it's a quick exercise. Include assumptions, research methods (even if hypothetical), design decisions, and rationale.
Present Clearly: Practice presenting your solution concisely and effectively, focusing on the "why" behind your design choices.

📝 Enhancement Note: The interview process is designed to assess not only design skills but also the ability to navigate complex product challenges, collaborate effectively, and understand the nuances of the healthcare industry. Your portfolio should explicitly address the requirements for designing complex systems and managing stakeholders.

🛠 Tools & Technology Stack

Primary Tools:

Figma: The core tool for UI design, wireframing, prototyping, and collaboration. Proficiency is essential for creating high-fidelity designs and interactive prototypes.
Prototyping Tools: Likely including advanced features within Figma or potentially other specialized tools for creating detailed interactive prototypes to showcase user flows and interactions.
AI-Assisted Design Tools: Explicit mention of tools like Claude Code indicates an expectation for designers to leverage AI for tasks such as generating code snippets, assisting with design documentation, or potentially brainstorming design solutions.

Analytics & Reporting:

Analytics Platforms: Familiarity with platforms like Google Analytics, Amplitude, or similar tools to understand user behavior, track key performance indicators (KPIs), and inform design decisions.
Data Visualization Tools: Experience with tools that can help interpret and present data, such as Tableau, Looker, or even advanced Excel/Google Sheets functions, to support hypothesis-driven research.

CRM & Automation:

CRM Systems: While not directly designing a CRM, understanding how products integrate with or complement CRM functionalities (e.g., Salesforce, HubSpot) is beneficial, especially for designing broker-facing tools that might interact with sales pipelines.
Workflow Automation Concepts: Understanding principles of workflow automation is crucial for designing efficient intake and enrollment processes.

📝 Enhancement Note: Proficiency in Figma is a baseline requirement. The inclusion of AI-assisted tools like Claude Code signifies a forward-looking approach to design workflows, suggesting that candidates who can articulate how they integrate such tools into their practice will stand out. Understanding how design impacts data and integrates with CRM systems is also highly relevant for marketplace and broker-facing tools.

👥 Team Culture & Values

Operations Values:

User Empathy: A deep commitment to understanding and advocating for the needs of users (brokers and consumers) to create meaningful and effective solutions.
Data-Driven Decision Making: Reliance on research, experimentation, and analytics to inform design choices and measure impact, moving beyond subjective preferences.
Collaboration & Transparency: Open communication and close partnership with cross-functional teams, fostering a shared understanding and collective ownership of product goals.
Craftsmanship & Quality: Maintaining a high standard for design execution, ensuring polished user experiences, robust interactions, and adherence to design systems.
Innovation & Adaptability: Embracing new technologies and methodologies, such as AI-assisted design tools, to continuously improve processes and product outcomes.
Humility & Determination: A balanced approach characterized by a humble desire to learn and grow, combined with a determined drive to achieve ambitious goals.

Collaboration Style:

Cross-functional Integration: Working seamlessly with Product, Engineering, Research, Data, and Marketing teams, ensuring design is integrated early and throughout the development process.
Constructive Feedback: An environment where feedback is regularly exchanged, constructively given, and openly received to improve designs and processes.
Shared Ownership: A culture where success is a team effort, with designers contributing to product strategy and problem-solving beyond just UI execution.
Proactive Communication: Regular updates, clear articulation of design rationale, and proactive engagement with stakeholders to manage expectations and build consensus.

📝 Enhancement Note: The values emphasize a blend of user advocacy, analytical rigor, and collaborative teamwork, all crucial for success in a product design role within a complex industry like healthcare. The mention of "humble yet determined" and "AI-assisted tools" suggests a culture that values both personal growth and technological advancement.

⚡ Challenges & Growth Opportunities

Challenges:

Navigating Healthcare Complexity: Designing for the healthcare industry involves understanding intricate regulations, diverse user needs (brokers, consumers, potentially ICHRA administrators), and sensitive data, which presents unique design challenges.
Balancing Stakeholder Needs: Effectively managing expectations and aligning design decisions across multiple stakeholders with potentially competing priorities.
Driving Adoption of New Tools: Encouraging brokers and consumers to adopt and effectively use new marketplace and enrollment platforms requires intuitive and highly usable design.
Technical Constraints: Working within technical limitations while still delivering excellent user experiences and innovative solutions.
Rapid Iteration in a Hybrid Environment: Maintaining design velocity and cohesive collaboration across a hybrid work model.

Learning & Development Opportunities:

Healthcare Domain Expertise: Deepen knowledge of the health insurance market, regulatory landscape, and consumer/broker behaviors.
Advanced Design Systems: Contribute to and evolve sophisticated design systems for a large-scale platform.
AI in Design: Explore and implement advanced AI tools and techniques to enhance design efficiency and creativity.
Product Strategy Influence: Grow from execution to influencing product strategy and roadmap decisions through impactful design contributions.
Mentorship: Receive guidance from senior design leaders and collaborate with experienced product and engineering teams.

📝 Enhancement Note: The role offers significant opportunities to tackle complex problems in a high-impact industry. The challenges are balanced by substantial growth potential, particularly in developing expertise in healthcare tech and leveraging cutting-edge design tools.

💡 Interview Preparation

Strategy Questions:

"Describe a time you designed a complex intake system or enrollment platform. What were the key challenges, and how did you overcome them?" (Focus on process, user flows, data management, and stakeholder alignment.)
"How do you balance the needs of different stakeholders (e.g., product, engineering, business) when making design decisions?" (Highlight your communication, negotiation, and rationale-sharing skills.)
"Walk me through a project where you used user research to significantly influence your design direction. What was your methodology, and what were the outcomes?" (Emphasize your research process and ability to translate insights into actionable designs.)

Company & Culture Questions:

"What interests you about Oscar Health and our mission to change healthcare?" (Research Oscar's values, recent news, and specific initiatives like Lucie Health.)
"How do you contribute to a collaborative team environment, especially in a hybrid setting?" (Share examples of your communication and teamwork style.)
"Describe your experience working with design systems. How do you ensure consistency and scalability?" (Discuss your understanding of design system principles and practical application.)

Portfolio Presentation Strategy:

Structure Your Narrative: For each project, follow a clear story: Problem -> Your Role -> Process -> Solution -> Impact -> Learnings.
Focus on "Why": Explain the rationale behind your design decisions at every stage. Why this approach? Why this feature? Why this interaction?
Show, Don't Just Tell: Use visuals effectively. Show wireframes, user flows, mockups, and prototypes. If possible, demonstrate interactive elements.
Quantify Results: Present metrics and data to support the success of your designs. If exact numbers aren't available, discuss how you would measure success.
Tailor to the Role: Emphasize projects that showcase experience with complex systems, B2B/broker platforms, or similar challenges to those faced by Lucie Health. Be ready to discuss your understanding of the healthcare context.

📝 Enhancement Note: Preparation should focus on demonstrating not just design skills but also strategic thinking, problem-solving capabilities, and the ability to navigate complex product and stakeholder landscapes, with a particular focus on the nuances of the healthcare marketplace.

📌 Application Steps

To apply for this Product Designer position:

Submit your application through the official Oscar Health careers portal via the provided link.
Customize Your Resume: Tailor your resume to highlight your 4+ years of Product/UX Design experience, specifically mentioning experience with complex web/mobile interfaces, intake systems, enrollment platforms, or CRM tooling, and at least 2 years of stakeholder management. Use keywords from the job description.
Curate Your Portfolio: Select 2-3 strong case studies that best showcase your ability to design complex systems, manage stakeholders, and articulate your design process. Ensure they demonstrate impact and align with the requirements of this role at Oscar Health.
Prepare Your Presentation: Rehearse presenting your portfolio projects, focusing on clear storytelling, demonstrating your process, quantifying impact, and explaining your design rationale. Be ready to discuss your experience with Figma and any familiarity with AI design tools.
Research Oscar Health: Understand Oscar's mission, values, and recent developments, particularly concerning the Lucie Health Marketplace, to articulate your genuine interest and cultural fit during interviews.

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

Product Designer, Marketplace