Product Designer, Marketplace

📍 Job Overview

Job Title: Product Designer, Marketplace

Company: Oscar Health

Location: New York, New York, United States

Job Type: Full-Time

Category: Product Design / UX Design

Date Posted: 2026-06-04

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

Remote Status: Hybrid

🚀 Role Summary

• Design and deliver user-centric digital products for Oscar Health's innovative Lucie Health Marketplace, focusing on enhancing the broker and consumer healthcare enrollment experience.

• Drive the end-to-end design process, from initial discovery and user research to high-fidelity prototyping and final delivery, ensuring seamless integration with existing systems and a scalable, intuitive user journey.

• Collaborate extensively with cross-functional teams including Product Management, Engineering, Research, Data Science, and Operations to translate complex requirements into elegant and effective design solutions.

• Leverage modern design workflows and AI-assisted tools to optimize the design-to-engineering handoff, accelerating development cycles while maintaining a high standard of craft and user empathy.

📝 Enhancement Note: This role is specifically focused on the 'Lucie Health Marketplace' initiative, which is a critical strategic project for Oscar Health aimed at revolutionizing healthcare shopping. The emphasis on the broker experience and complex intake/enrollment systems suggests a need for a designer proficient in B2B or internal tool design, in addition to consumer-facing product design. The mention of AI-assisted tools like Claude Code highlights a forward-thinking approach to design and development workflows.

📈 Primary Responsibilities

• Execute product design strategies within the Lucie Health Marketplace, with a strong emphasis on the broker experience, ICHRA tooling, and direct enrollment platforms.

• Conduct hypothesis-driven user research, prototyping, and experimentation to gather actionable insights and inform design decisions, ensuring a deep understanding of user needs and pain points.

• Develop comprehensive design solutions, including user flows, wireframes, interactive prototypes, and high-fidelity visual designs, for both web and mobile interfaces.

• Collaborate closely with Product Managers to define product requirements, translate business goals into user-centered designs, and ensure alignment with overall product strategy.

• Partner with Engineers to ensure accurate implementation of designs, troubleshoot technical constraints, and maintain design integrity throughout the development lifecycle.

• Maintain and contribute to Oscar Health's design system, ensuring consistency, scalability, and adherence to brand guidelines across all product experiences.

• Facilitate and participate in design workshops, visioning sessions, and cross-functional meetings to drive consensus and foster a collaborative design culture.

• Translate complex healthcare insurance concepts and regulatory requirements into simple, accessible, and user-friendly interfaces.

📝 Enhancement Note: The core responsibility of executing the design process with guidance on complex problems and considering long-term impact with near-term polish points to a need for a designer who can balance strategic thinking with tactical execution. The emphasis on hypothesis-driven research and experimentation suggests a data-informed design approach is highly valued.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience.

Experience: 4+ years of experience in Product/UX Design, with a demonstrable track record of designing and shipping complex web and mobile interfaces. A minimum of 2 years of experience directly managing and collaborating with stakeholders is also required.

Required Skills:

• Proven expertise in the end-to-end product design process, including user research, wireframing, prototyping, and visual design.

• Strong proficiency in industry-standard design tools, particularly Figma, for creating high-fidelity mockups and interactive prototypes.

• Demonstrated ability to design and ship complex web and mobile interfaces, with at least two concrete examples to showcase.

• Experience in stakeholder management, effectively communicating design decisions and gathering feedback from cross-functional teams and leadership.

• Solid understanding of interaction design principles and best practices for creating intuitive user experiences.

• Ability to translate complex requirements, user insights, and technical constraints into elegant and user-friendly UI solutions.

Preferred Skills:

• Experience within the healthcare industry, particularly with health insurance marketplaces, enrollment platforms, or related FinTech/HealthTech products.

• Proficiency with AI-assisted design tools (e.g., Claude Code) to streamline the design-to-engineering workflow.

• Experience with creating animated prototypes or detailed user flow diagrams to effectively communicate design concepts and user journeys.

• Familiarity with design ethics, accessibility standards (WCAG), and their application in healthcare contexts.

• Demonstrated ability to manage design contributions across high-performing web, mobile, or internal tool products.

• Experience with user research methodologies and the ability to translate research findings into actionable design improvements.

• A genuine, inquisitive, humble, yet determined professional attitude.

📝 Enhancement Note: The requirement for 2+ years of stakeholder management is a significant indicator of the role's expectation for a designer who can influence product direction and communicate effectively with diverse groups, including potentially senior leadership and external partners. The preference for healthcare experience and AI tool proficiency suggests Oscar Health is looking for specialized skills within a rapidly evolving industry.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least two complex web or mobile interface projects that have been successfully designed and shipped, demonstrating end-to-end ownership from concept to launch.

• Include detailed case studies that illustrate your design process, problem-solving approach, and the impact of your contributions on user experience and business outcomes.

• Highlight projects involving complex intake systems, enrollment platforms, or CRM tooling, with specific attention to how you addressed user needs and business objectives.

• Demonstrate strong visual design craft and interaction design skills through high-fidelity mockups, prototypes, or live product examples.

Process Documentation:

• Emphasize your ability to conduct hypothesis-driven research, outlining how you formulate hypotheses, design experiments, and derive actionable insights.

• Showcase your experience with prototyping and iterating based on user feedback and data.

• Provide examples of how you have translated user research and requirements into simple, useful, and scalable UI designs.

• Illustrate your understanding of design systems and how you maintain consistency and leverage existing components in your work.

📝 Enhancement Note: Given the role's focus on complex systems like enrollment platforms and CRM tooling, the portfolio should explicitly detail how the candidate approaches designing for intricate workflows, data management, and user journeys within such environments. Demonstrating experience with both consumer-facing and potentially internal/broker-facing tools will be crucial.

💵 Compensation & Benefits

Salary Range: $123,372.00 - $161,925.75 per year. This range is determined by factors including relevant skills, education, and experience.

Benefits:

• Comprehensive Medical, Dental, and Vision Insurance.

• 11 Paid Holidays.

• Paid Sick Time.

• Paid Parental Leave.

• 401(k) Plan participation.

• Life Insurance.

• Disability Insurance.

• Paid Wellness Time.

• Wellness Reimbursements.

• Unlimited Vacation Program.

• Company Equity Grants.

• Annual Performance Bonuses.

Working Hours: Standard full-time hours, typically around 40 hours per week. The hybrid work arrangement allows for flexibility in scheduling office days, with Thursdays designated for in-office team meetings and events.

📝 Enhancement Note: The provided salary range is competitive for a Product Designer role in New York City, especially with the specified experience level and the specialized nature of the healthcare marketplace domain. The extensive benefits package, including unlimited vacation, equity, and bonuses, indicates a comprehensive compensation structure designed to attract and retain top talent.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance Technology (HealthTech), Software, Healthcare. Oscar Health is a pioneer in leveraging technology to create a more accessible and user-friendly health insurance experience.

Company Size: Oscar Health is a growing company, part of the broader technology and healthcare sectors. Its size suggests a dynamic environment with opportunities for impact, while also maintaining structured processes and cross-functional collaboration.

Founded: Oscar Health was founded in 2012 with the mission to create a better health insurance experience, operating like a "doctor in the family." This founding principle of user-centricity and innovation likely permeates its current culture.

Team Structure:

• The Product Design team is part of a larger Product organization, working closely with Product Management, Engineering, Research, and Data Science.

• This role reports to the Sr. Director, Product Design, indicating a clear reporting line and potential for mentorship from senior design leadership.

Methodology:

• Oscar Health emphasizes a hypothesis-driven approach to product development, involving research, prototyping, and launching experiments to validate ideas and gather insights.

• The company utilizes modern workflows and is open to leveraging AI-assisted tools to enhance efficiency in the design-to-engineering process.

• A strong focus on user empathy and delivering a consistent, scalable, and intuitive experience across its product suite is evident.

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

📝 Enhancement Note: The company's mission to revolutionize healthcare through technology suggests a culture of innovation, problem-solving, and a strong user-centric mindset. The integration of AI tools indicates a commitment to adopting cutting-edge technologies to improve workflows and outcomes.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a mid-level (2-5 years) of Product/UX Design. It offers the opportunity to take ownership of significant product areas (Lucie Health Marketplace) and contribute to strategic initiatives. The role involves executing design processes with guidance but also requires autonomy and the ability to manage stakeholders directly.

Reporting Structure: The Product Designer will report to the Sr. Director, Product Design. This structure provides access to senior design leadership, mentorship, and exposure to higher-level design strategy and decision-making.

Operations Impact: The Product Designer will have a direct impact on how consumers and brokers interact with and enroll in healthcare coverage through the Lucie Health Marketplace. This includes shaping critical user journeys, driving adoption of new platforms, and contributing to Oscar Health's overall mission of simplifying healthcare. The success of the Marketplace directly influences revenue and member acquisition.

Growth Opportunities:

• Skill Specialization: Deepen expertise in designing complex marketplaces, enrollment systems, and B2B/internal tools within the HealthTech sector.

• Leadership Potential: Develop leadership skills through direct stakeholder management, leading design initiatives, and potentially mentoring junior designers as the team grows.

• Cross-functional Expertise: Gain extensive experience working with diverse teams (Product, Engineering, Data, Marketing, Brand) and understanding the interplay of different functions in a tech-driven healthcare company.

• Strategic Contribution: Contribute to the strategic direction of the Lucie Health Marketplace, influencing product roadmap and design vision.

• Industry Knowledge: Build significant knowledge in healthcare insurance, regulatory landscapes, and consumer/broker behavior in this complex market.

📝 Enhancement Note: The role offers a clear path for growth from a mid-level designer to a more senior or specialized role, particularly within the complex and high-impact HealthTech domain. The opportunity to shape a new, strategic product like the Lucie Health Marketplace provides significant career development potential.

🌐 Work Environment

Office Type: Oscar Health operates with a hybrid work model, requiring 3 days in the New York City office per week. This promotes a balance between focused individual work and collaborative in-person interaction.

Office Location(s): The primary work location is the New York City office. Specific details regarding office amenities and accessibility would typically be available through company resources.

Workspace Context:

• The workspace is designed to foster collaboration, with dedicated in-office days for team meetings, design critiques, and cross-functional brainstorming sessions.

• Access to modern design tools and technology, including Figma and AI-assisted design tools, is expected to support efficient and innovative design processes.

• Opportunities for regular interaction with product managers, engineers, researchers, and other designers will facilitate knowledge sharing and collective problem-solving.

Work Schedule: While the standard workweek is typically 40 hours, the hybrid model and unlimited vacation policy suggest a culture that values work-life balance and employee well-being, while still expecting high performance and delivery.

📝 Enhancement Note: The hybrid model with a mandatory in-office day (Thursdays) is a key aspect of the work environment, designed to maximize collaboration and team cohesion. This structure is common in tech companies aiming to retain the benefits of in-person interaction while offering flexibility.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter will likely review your application and resume, focusing on experience level, relevant skills, and alignment with the role's core requirements.

• Portfolio Review & Design Challenge: Expect to present your portfolio, highlighting 2+ concrete examples of designing and shipping complex web/mobile interfaces. This may be followed by a design challenge or a deep dive into one of your portfolio projects, assessing your problem-solving abilities, design process, and communication skills.

• Cross-functional Interviews: You will likely interview with Product Managers, Engineers, and potentially other designers or stakeholders to assess your collaboration style, technical understanding, and ability to work within a team.

• Hiring Manager Interview: A final interview with the Sr. Director, Product Design, to discuss your experience, career aspirations, and cultural fit.

Portfolio Review Tips:

• Showcase Complexity: Focus on the 2+ required examples of complex web/mobile interfaces. Clearly articulate the problem, your process, the solutions you designed, and the impact.

• Highlight Broker/Enrollment Experience: Given the role's focus, prominently feature any projects related to intake systems, enrollment platforms, CRMs, or B2B tools.

• Demonstrate Impact: Quantify the success of your designs where possible (e.g., user engagement, conversion rates, efficiency improvements).

• Explain Your Process: Detail your approach to user research, problem-solving, iteration based on feedback, and collaboration with engineering.

• Visual Craft & Interaction: Ensure your portfolio visually communicates strong design skills, attention to detail, and thoughtful interaction design.

• AI Tool Integration: If you've used AI-assisted tools (like Claude Code) to enhance your workflow, mention it and explain its benefits in your case studies.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with the healthcare insurance market, common user pain points for consumers and brokers, and the typical enrollment process.

• Practice Problem-Solving: Be prepared to tackle a design problem related to the Lucie Health Marketplace, focusing on user needs, business goals, and technical constraints.

• Articulate Your "Why": Clearly explain the rationale behind your design decisions, connecting them back to user research, business objectives, and design principles.

• Scenario-Based Questions: Expect questions about how you would handle specific design challenges, stakeholder disagreements, or technical limitations.

📝 Enhancement Note: The emphasis on 2+ concrete examples of shipping complex interfaces, coupled with stakeholder management experience, means candidates should be prepared to discuss specific projects in depth and articulate their ability to navigate organizational dynamics. The specific mention of AI tools suggests interviewers may probe on how these tools were leveraged.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for wireframing, prototyping, visual design, and collaboration. Proficiency is essential for creating high-fidelity mockups and maintaining design systems.

• AI-assisted Design Tools (e.g., Claude Code): Mentioned as a tool to streamline the design-to-engineering process. Familiarity with leveraging AI for code generation or design assistance would be a significant plus.

• Prototyping Tools: Beyond Figma's capabilities, experience with specialized prototyping tools might be beneficial for complex animations or interactive user flow diagrams.

Analytics & Reporting:

CRM & Automation:

• Experience designing for or within CRM systems (e.g., Salesforce) or enrollment automation platforms is highly relevant given the role's focus on the Lucie Health Marketplace. Understanding the data structures and workflows common in these systems will be advantageous.

• Design Systems: Experience building, contributing to, or utilizing robust design systems for consistency and scalability across platforms.

📝 Enhancement Note: The explicit mention of Figma and AI-assisted tools like Claude Code indicates a modern, tech-forward design environment. Designers should be ready to discuss their proficiency with Figma and any experience they have with AI tools in their design workflow.

👥 Team Culture & Values

Operations Values:

• User Empathy: A deep commitment to understanding and serving the needs of users (brokers and consumers) is central to Oscar Health's mission and product development.

• Innovation & Technology: Embracing new technologies, including AI, to improve user experiences and operational efficiency is a key driver for the company.

• Collaboration: A strong emphasis on cross-functional teamwork, open communication, and shared problem-solving across departments.

• Execution Speed & Quality: Balancing the need for rapid iteration and delivery with a high standard of design craft and user experience.

• Data-Driven Decision-Making: Utilizing research, experiments, and analytics to inform design choices and measure impact.

Collaboration Style:

• Cross-functional Integration: Designers are expected to work seamlessly with Product Managers, Engineers, Researchers, and Data Scientists, acting as a bridge between user needs and technical implementation.

• Open Feedback Culture: A willingness to give and receive constructive feedback on designs and processes to foster continuous improvement.

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

📝 Enhancement Note: The company's values suggest a collaborative and results-oriented environment where designers are empowered to take ownership and drive innovation. The emphasis on user empathy and technology integration is core to Oscar Health's identity.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of Healthcare Domain: Navigating the intricate landscape of health insurance, regulations, and diverse user needs (brokers vs. consumers) presents a significant design challenge.

• Balancing User Needs with Business Goals: Effectively designing for both user experience and business objectives within a competitive marketplace requires strategic thinking and compromise.

• Technical Constraints: Working within established technical architectures and limitations while striving for innovative solutions.

• Rapidly Evolving Technology: Staying abreast of new design tools, AI advancements, and best practices in a fast-paced tech environment.

Learning & Development Opportunities:

• Specialized HealthTech Design: Gaining deep expertise in designing for the healthcare industry, a complex but high-impact sector.

• Leadership Development: Opportunities to lead design initiatives, influence product strategy, and potentially mentor junior team members.

• Advanced Tool Proficiency: Mastering AI-assisted design tools and other emerging technologies to enhance design workflows.

• Cross-functional Mastery: Developing a comprehensive understanding of product development lifecycles across various disciplines within a tech company.

📝 Enhancement Note: The challenges presented are typical for roles in innovative HealthTech companies, requiring adaptability and a strong problem-solving mindset. The growth opportunities are significant, offering a path to specialized expertise and leadership within a rapidly expanding field.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design for complex user flows or intake systems. What was your approach, and what was the outcome?" (Focus on process, problem-solving, and impact.)

• "How do you balance user needs with business requirements and technical constraints when designing a new feature or product?" (Assess strategic thinking and negotiation skills.)

Company & Culture Questions:

• "What interests you about Oscar Health and the Lucie Health Marketplace specifically?" (Showcase research and genuine interest in the company's mission.)

• "How do you approach user research and incorporate user feedback into your design process?" (Demonstrate user-centricity and data-informed design.)

Portfolio Presentation Strategy:

• Tell a Story: For each case study, craft a narrative that clearly outlines the problem, your role, your process, the challenges faced, your solutions, and the measurable impact.

• Focus on Process: Be prepared to deep-dive into your design process, explaining the "why" behind your decisions, the tools you used, and how you iterated.

• Highlight Key Requirements: Explicitly point out the 2+ complex interface examples and any stakeholder management experiences within your presented projects.

• Visual Clarity: Ensure your slides or digital presentation are clean, well-organized, and visually appealing, reflecting your design craft.

• Be Concise: Respect the allotted time and focus on the most critical aspects of each project.

📝 Enhancement Note: Candidates should prepare to discuss specific projects in detail, focusing on quantifiable results and their personal contributions. Understanding Oscar Health's mission and the strategic importance of the Lucie Health Marketplace will be crucial for demonstrating cultural fit and vision alignment.

📌 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 your 4+ years of Product/UX Design experience, specifically mentioning your success in designing and shipping complex web/mobile interfaces and your 2+ years of stakeholder management. Use keywords from the job description.

• Curate your portfolio: Select 2-3 of your strongest projects that best demonstrate your ability to design complex systems (enrollment platforms, CRMs, marketplaces) and your end-to-end design process. Ensure each case study clearly articulates the problem, your process, your solutions, and the impact.

• Prepare your narrative: Practice presenting your portfolio projects, focusing on telling a compelling story about how you solved user problems and contributed to business success. Be ready to discuss your challenges, decisions, and learnings.

• Research Oscar Health: Understand the company's mission, values, and the strategic significance of the Lucie Health Marketplace. Prepare to articulate why you are a good fit for their culture and this specific role.

⚠️ 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.