Product Designer, Marketplace at Oscar Health

📍 Job Overview

Job Title: Product Designer, Marketplace

Company: Oscar Health

Location: Boston, Massachusetts, United States

Job Type: Full-Time

Category: Product Design / UX Design

Date Posted: June 04, 2026

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

Remote Status: Fully Remote (Boston, MA)

🚀 Role Summary

Design and deliver user-centric interfaces for Oscar Health's innovative Lucie Health Marketplace, focusing on the broker and consumer healthcare enrollment experience.
Collaborate cross-functionally with Product Management, Engineering, Research, Data, and Operations to translate complex user needs into intuitive, scalable, and high-fidelity design solutions.
Leverage a strong foundation in visual and interaction design, coupled with advanced skills in Figma and AI-assisted design tools, to drive features from discovery through delivery.
Contribute to a modern design workflow, ensuring seamless integration between design and engineering processes, and maintaining a high bar for user experience and design system consistency.

📝 Enhancement Note: This role is specifically for a Product Designer focused on user experience within a healthcare marketplace platform, emphasizing the broker and consumer enrollment journey. The role requires a blend of creative design skills, strategic thinking, and technical proficiency, with a strong emphasis on collaboration and delivering tangible product features. The mention of AI-assisted tools like Claude Code highlights a forward-thinking approach to design workflows.

📈 Primary Responsibilities

Execute the end-to-end design process for the Lucie Health Marketplace, including complex intake systems, enrollment platforms, and ICHRA tooling, with a primary focus on the broker experience.
Conduct hypothesis-driven user research, prototyping, and A/B testing to gather actionable insights and inform product strategy and design solutions.
Collaborate closely with Product Managers, Engineers, Researchers, Marketers, Brand Designers, and Operations stakeholders to ensure alignment and successful feature delivery.
Develop a deep understanding of user needs and market dynamics within the healthcare insurance sector to drive innovation and create impactful user experiences.
Maintain and contribute to Oscar's design system, ensuring brand consistency, scalability, and high-quality craft across all product touchpoints.
Translate user requirements, research findings, and business goals into simple, useful, and aesthetically pleasing UI designs for both web and mobile interfaces.
Lead or contribute to design workshops, visioning sessions, and presentations to articulate design rationale and influence product direction.
Champion design ethics, accessibility standards, and best practices relevant to the healthcare industry to ensure inclusive and compliant product experiences.
Manage stakeholder expectations and communications effectively throughout the design lifecycle, ensuring buy-in and alignment on design decisions.
Ensure compliance with all applicable laws and regulations within the healthcare industry.

📝 Enhancement Note: The responsibilities highlight a comprehensive product design role involving strategy, research, execution, and stakeholder management. The emphasis on "complex intake systems, enrollment platforms, or CRM tooling" and the "broker experience" within the "Lucie Health Marketplace" provides specific context for the types of problems this designer will solve. The inclusion of "hypothesis-driven research, prototyping and launching experiments" points to a data-informed design approach.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design (e.g., Graphic Design, Interaction Design, HCI) or a related field, or equivalent practical experience, is highly recommended for a role of this nature.

Experience: 4+ years of progressive experience in Product Design or UX Design, with a demonstrated ability to design and ship complex, high-impact web and mobile interfaces. 2+ years of direct experience managing and collaborating with cross-functional stakeholders is essential.

Required Skills:

Product Design & UX: Proven ability to conceptualize, design, and deliver intuitive and effective user experiences for complex digital products.
Visual & Interaction Design: Strong craft in visual design principles, typography, layout, and interaction patterns that create engaging and usable interfaces.
Figma Proficiency: Expert-level skills in Figma for wireframing, prototyping, high-fidelity design, and component-based design systems.
User Research & Prototyping: Experience conducting user research (qualitative and quantitative) and creating interactive prototypes to validate design concepts.
Stakeholder Management: Demonstrated ability to effectively communicate design rationale, gather feedback, and manage expectations with product managers, engineers, and business leaders.
Complex System Design: Experience designing intricate systems such as intake platforms, enrollment flows, or CRM tooling.
Web & Mobile Interface Design: Proven track record of designing and shipping successful interfaces for both web and mobile applications.
Design Systems: Understanding and experience contributing to or utilizing design systems to ensure consistency and scalability.

Preferred Skills:

Healthcare Industry Experience: Familiarity with the healthcare insurance landscape, including regulations, user needs, and common workflows.
Storytelling & Communication: Ability to effectively communicate design ideas through animated prototypes, user flow diagrams, and compelling presentations.
Design Ethics & Accessibility: A strong understanding of design ethics, accessibility standards (WCAG), and their application in user-centered design, particularly within healthcare.
AI-Assisted Design Tools: Experience leveraging AI tools (e.g., Claude Code) to enhance design workflows and accelerate the design-to-engineering handoff.
ICHRA & Direct Enrollment: Knowledge or experience with Individual Coverage Health Reimbursement Arrangements (ICHRA) or direct consumer/broker enrollment platforms.
Agile Development: Experience working within agile development methodologies and cross-functional agile teams.

📝 Enhancement Note: The requirements clearly point to a mid-level product designer role. The emphasis on "4+ years of experience" and "2+ years managing stakeholders" aligns with this. The specific mention of "complex web and mobile interfaces" and "complex intake systems, enrollment platforms, or CRM tooling" indicates the need for a designer who can handle intricate user flows and business logic, not just aesthetic design. The bonus points for healthcare experience and AI tool usage are significant differentiators.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

Demonstrated Impact: Showcase at least 2 concrete examples of complex web and mobile interfaces that you have designed and successfully shipped, clearly articulating your role and contributions.
Process Visualization: Include user flow diagrams, wireframes, and interactive prototypes that illustrate your design process from problem identification to solution delivery.
System Design Examples: Highlight projects that demonstrate your ability to design complex systems, such as intake processes, enrollment platforms, or internal tooling, emphasizing user journeys and data flow.
Stakeholder Collaboration: Provide evidence of how you managed stakeholders, incorporated feedback, and navigated cross-functional discussions to achieve design goals.
Design System Contribution: If applicable, showcase examples of how you have worked with or contributed to design systems, demonstrating an understanding of consistency and scalability.

Process Documentation:

User-Centered Design Workflow: Clearly document your approach to user research, ideation, wireframing, prototyping, and high-fidelity design, explaining the rationale behind each step.
Problem-Solving Case Studies: Present case studies that detail a specific design challenge, your problem-solving methodology, the constraints you faced (technical, business), and the final design solution with its measurable impact.
Collaboration & Handoff: Illustrate your process for collaborating with engineering and product management, including how you translate design specifications and ensure successful implementation.

📝 Enhancement Note: For a Product Designer role, a strong portfolio is paramount. The emphasis on "2 concrete examples of designing and shipping complex web and mobile interfaces" and "complex intake systems, enrollment platforms, or CRM tooling" means candidates should be prepared to showcase projects that clearly demonstrate these capabilities. The inclusion of "stakeholder management" and "AI-assisted tools" suggests that the portfolio should ideally highlight how these aspects were integrated into their work.

💵 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
Paid Wellness Time
Wellness Reimbursements
Unlimited Vacation Program
Company Equity Grants
Annual Performance Bonuses

Working Hours: Standard full-time hours (likely 40 hours per week), with flexibility often inherent in remote roles, allowing for focused work periods and effective integration of personal time, particularly important for roles that may involve cross-functional collaboration across different time zones or require deep concentration.

📝 Enhancement Note: The provided salary range is specific. The benefits list is comprehensive, with notable inclusions like unlimited vacation, equity grants, and annual bonuses, which are attractive for mid-level professionals. The "Working Hours" are described with an operations-minded perspective, highlighting flexibility and focus.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology / Health Insurance

Company Size: Oscar Health is a significant player in the health insurance market, employing over 1,000 individuals, which suggests a dynamic, growth-oriented environment with established processes but opportunities for influence. This size often means cross-functional teams are well-defined, but collaboration across departments is crucial.

Founded: 2012. Founded on the principle of creating a more human-centered health insurance experience, Oscar Health has a history of innovation and leveraging technology to achieve its mission. This founding ethos likely permeates its current culture, emphasizing member-centricity and technological advancement.

Team Structure:

The Product Design team is led by a Sr. Director, Product Design, indicating a structured hierarchy with clear leadership.
This role will work closely with a Senior Product Designer dedicated to the Lucie Marketplace, suggesting a mentorship or collaborative partnership for complex projects.

Methodology:

Data-Driven Design: The role emphasizes "hypothesis-driven research, prototyping and launching experiments," indicating a strong reliance on data and user feedback to inform design decisions.
Agile Development: Collaboration with engineering teams in a modern workflow suggests an agile or iterative development process where designs are developed and refined in cycles.
User Empathy: A core tenet is "deep user empathy," which translates into designing solutions that genuinely meet the needs of brokers and consumers in the complex healthcare landscape.

Company Website: http://www.hioscar.com/careers/7981447?gh_jid=7981447

📝 Enhancement Note: Oscar Health's mission to revolutionize healthcare through technology implies a culture that values innovation, user-centricity, and data-driven decision-making. The "Product Designer, Marketplace" role is positioned within a specific, growth-focused initiative (Lucie Health Marketplace), suggesting an environment where designers can have a tangible impact on a new and critical business area.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as a mid-level Product Designer. It requires significant autonomy in execution and a strong ability to manage stakeholders, but also involves working under the guidance of a Senior Product Designer and reporting to a Director. It's a position where an individual can deepen their expertise in complex system design within the healthcare domain.

Reporting Structure: The Product Designer will report to the Sr. Director, Product Design. They will also work closely with a Senior Product Designer on the Lucie Marketplace initiative, indicating a supportive and collaborative reporting structure.

Operations Impact: The Product Designer will directly influence the success of the Lucie Health Marketplace by designing the tools that brokers and consumers use to navigate and enroll in healthcare coverage. This role has a direct impact on revenue generation (through successful enrollment and retention) and operational efficiency (by creating intuitive tools that reduce support needs and streamline processes).

Growth Opportunities:

Specialization: Deepen expertise in healthcare technology design, focusing on complex marketplace dynamics, enrollment systems, and broker-specific tooling.
Leadership Potential: Develop leadership skills through mentoring from a Senior Product Designer, leading design initiatives within the marketplace, and potentially growing into a Senior Product Designer role.
Cross-Functional Impact: Gain broader experience by collaborating closely with various departments, understanding the operational and business implications of design decisions.
Skill Development: Opportunity to hone skills in AI-assisted design tools, advanced prototyping, and user research methodologies relevant to the healthcare sector.

📝 Enhancement Note: This role offers a clear path for growth within product design, especially within the specialized and high-impact healthcare technology sector. The emphasis on a "Marketplace" initiative and "broker experience" provides a niche for specialization. The reporting structure to a Sr. Director and collaboration with a Senior Designer suggests structured mentorship and development.

🌐 Work Environment

Office Type: This position is designated as fully remote, with the candidate residing in Boston, MA. While currently remote, the company notes that future work models may adapt, potentially including hybrid presence at a hub office. This indicates a flexible approach to work arrangements.

Office Location(s): While the role is remote, the primary hub associated with this role is Boston, Massachusetts. This suggests that Oscar Health has a physical presence or operational focus in this metropolitan area.

Workspace Context:

Remote Collaboration: The work environment relies heavily on digital collaboration tools and effective asynchronous communication to maintain team cohesion and productivity across distributed teams.
Technology-Centric: Access to modern design software (Figma), AI-assisted tools, and communication platforms is essential for this role.
Cross-Functional Interaction: Opportunities for interaction will be primarily with virtual teams across Product, Engineering, Research, and Operations, fostering a collaborative and integrated work style.

Work Schedule: Standard full-time hours are expected, with the flexibility often associated with remote work. This allows for dedicated periods for deep design work, user research, and collaborative sessions, ensuring alignment with team needs and project deadlines.

📝 Enhancement Note: The remote nature of the role, while based in a specific geographic area (Boston), highlights a modern work environment that prioritizes flexibility and digital collaboration. The mention of potential future hybrid models suggests adaptability. The focus on technology and cross-functional interaction is key for a remote operations-adjacent role.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: A recruiter will likely assess your resume and portfolio for alignment with the core requirements, focusing on experience with complex systems, stakeholder management, and design craft.
Design Challenge/Portfolio Review: Expect a session where you present your portfolio, discussing 1-2 key projects in detail. This will likely involve explaining your process, design decisions, the impact of your work, and how you navigated challenges. A design exercise or take-home challenge focused on a marketplace or enrollment scenario might also be part of this stage.
Cross-Functional Interviews: You will likely meet with Product Managers, Engineers, and potentially other designers or researchers to assess your collaboration style, technical understanding, and fit within the team.
Hiring Manager Interview: A final interview with the Sr. Director, Product Design, to discuss your career aspirations, approach to design leadership, and overall fit with the company culture.

Portfolio Review Tips:

Focus on Impact: Clearly articulate the problem you solved, your role, the design process, and the measurable outcomes or impact of your work. Quantify results whenever possible (e.g., increased conversion rates, reduced user errors).
Showcase Complexity: Highlight projects involving complex intake systems, enrollment flows, or intricate user journeys. Explain how you simplified these complexities for the end-user.
Demonstrate Collaboration: Be prepared to discuss how you worked with stakeholders, incorporated feedback, and collaborated with engineering and product teams.
Highlight Process: Walk through your design process, from research and ideation to prototyping and final delivery. Explain the rationale behind your decisions.
Tailor to Oscar: If possible, subtly tailor your examples to align with Oscar's mission in healthcare and the specific needs of a marketplace platform. Mention your experience with AI tools if applicable.

Challenge Preparation:

Understand the Domain: Familiarize yourself with healthcare marketplaces, insurance enrollment processes, and the challenges faced by brokers and consumers.
Think Systemically: Practice designing for complex systems rather than isolated features. Consider edge cases, error states, and scalability.
Problem-Solving: Be ready to tackle hypothetical design problems related to user acquisition, onboarding, or feature optimization within a marketplace context.
Communication: Practice articulating your design thinking clearly and concisely, as if presenting to a mixed audience of designers, engineers, and product stakeholders.

📝 Enhancement Note: The interview process is typical for a mid-level product design role, emphasizing portfolio presentation and cross-functional collaboration. The "challenge preparation" section is tailored to the specific domain of a healthcare marketplace, advising candidates to think about systemic design and domain-specific issues.

🛠 Tools & Technology Stack

Primary Tools:

Figma: The core design and prototyping tool for all UI/UX work, including design system management.
AI-Assisted Design Tools: Explicitly mentioned is Claude Code, suggesting an expectation for designers to leverage AI for code generation, design assistance, or workflow optimization. Other similar tools may also be relevant.
Prototyping Tools: Beyond Figma's capabilities, specialized tools for complex animations or interactive prototypes might be utilized.
Design Systems: Experience working with or contributing to established design systems.

Analytics & Reporting:

Data Visualization Tools: Familiarity with tools like Tableau, Looker, or similar platforms used to understand user behavior and product performance metrics.
Analytics Platforms: Experience with product analytics tools (e.g., Amplitude, Mixpanel) to track user engagement, conversion funnels, and feature adoption.

CRM & Automation:

CRM Systems: While not directly designing the CRM, understanding how user data and enrollment information flows into and out of CRM systems (like Salesforce) is beneficial for designing integrated experiences.
Workflow Automation: Awareness of how design impacts automated workflows in areas like lead nurturing, onboarding, or customer support.

📝 Enhancement Note: The explicit mention of Figma and AI-assisted tools like Claude Code is critical. This indicates a modern, efficient design workflow where designers are expected to be proficient with industry-standard tools and embrace new technologies to enhance productivity and collaboration with engineering.

👥 Team Culture & Values

Operations Values:

Member-Centricity: A deep commitment to understanding and serving the needs of Oscar Health's members (consumers and brokers) through thoughtful design.
Innovation & Technology: A drive to leverage technology, including AI, to build better healthcare solutions and improve efficiency.
Collaboration & Transparency: Open communication and a willingness to work closely with diverse teams to achieve shared goals.
Data-Driven Decision Making: Utilizing data and user insights to validate hypotheses and guide design and product strategy.
Humility & Determination: A blend of being inquisitive and humble while remaining determined to overcome challenges and deliver results.

Collaboration Style:

Cross-Functional Partnership: A highly collaborative approach, working hand-in-hand with Product Management, Engineering, Research, Data, and Operations to ensure holistic product development.
Iterative Feedback: Embracing a culture of continuous feedback and iteration, where designs are shared early and often for input and refinement.
Knowledge Sharing: A proactive approach to sharing learnings, best practices, and design insights across teams to foster collective growth and efficiency.

📝 Enhancement Note: Oscar Health's values emphasize a human-centered approach to healthcare, driven by technology and data. The "humble yet determined" characteristic is particularly insightful for candidates, suggesting a need for adaptable, resilient individuals who can contribute constructively within a fast-paced environment.

⚡ Challenges & Growth Opportunities

Challenges:

Navigating Healthcare Complexity: Designing for the intricate and highly regulated healthcare industry, balancing user needs with compliance requirements and technical constraints.
Balancing Speed and Quality: Delivering against aggressive timelines for new marketplace features while maintaining a high standard of design craft, user experience, and system integrity.
Cross-Functional Alignment: Ensuring consistent vision and execution across multiple departments (Product, Engineering, Operations, Marketing) that may have competing priorities.
Evolving Technology: Staying current with AI advancements and integrating them effectively into design workflows without compromising user experience or core design principles.

Learning & Development Opportunities:

Healthcare Domain Expertise: Deepen understanding of insurance markets, enrollment processes, and the unique challenges faced by consumers and brokers.
AI in Design: Gain practical experience and expertise in leveraging AI-assisted tools for design and development workflows.
Complex System Design: Enhance skills in architecting and designing large-scale, multi-faceted digital platforms like marketplaces and enrollment systems.
Mentorship & Leadership: Benefit from guidance from a Sr. Director and Senior Product Designer, with opportunities to lead design initiatives and grow into more senior roles.

📝 Enhancement Note: The challenges are directly tied to the industry and the specific nature of the role. The growth opportunities are framed around developing specialized domain knowledge and leveraging cutting-edge technology, making this an attractive role for ambitious designers.

💡 Interview Preparation

Strategy Questions:

"Describe a time you designed a complex intake or enrollment system. What were the key challenges, and how did you simplify the user experience?" (Focus on process, problem-solving, and impact).
"How do you approach stakeholder management when design decisions are met with resistance or differing opinions?" (Highlight communication, negotiation, and data-driven advocacy).
"Walk us through a project where you had to balance aggressive timelines with maintaining high design quality. What trade-offs did you make, and what was the outcome?" (Demonstrate execution under pressure and strategic decision-making).

Company & Culture Questions:

"What interests you about Oscar Health and our mission to change healthcare?" (Research Oscar's mission, values, and recent news).
"How do you see yourself contributing to a culture that values 'humble yet determined' individuals?" (Reflect on your collaborative style and resilience).

Portfolio Presentation Strategy:

Storytelling: Structure your portfolio presentations as compelling narratives: The Problem, Your Role, The Process, The Solution, and The Impact.
Visual Clarity: Ensure your visuals are clean, well-organized, and clearly communicate the user flows, UI elements, and key design decisions.
Quantify Impact: Whenever possible, use metrics to demonstrate the success of your designs (e.g., conversion rates, user satisfaction scores, efficiency gains).
Focus on Process & Rationale: Be prepared to explain why you made certain design decisions, referencing user research, business goals, and technical constraints.
Address Collaboration: Explicitly discuss how you collaborated with product managers, engineers, and other stakeholders throughout the project lifecycle.

📝 Enhancement Note: The interview preparation advice is tailored to the specific requirements of the role, emphasizing complex systems, stakeholder management, and the unique aspects of working in healthcare technology with AI tools.

📌 Application Steps

To apply for this Product Designer position:

Submit your application through the Oscar Health careers portal via the provided URL.
Portfolio Customization: Ensure your portfolio prominently features at least two detailed case studies of complex web/mobile interfaces you've designed and shipped, ideally showcasing intake systems, enrollment platforms, or similar intricate user journeys.
Resume Optimization: Tailor your resume to highlight your 4+ years of experience in Product/UX Design, specific experience with Figma and AI-assisted tools, and your proven ability to manage stakeholders and deliver complex projects. Use keywords like "Marketplace Design," "Enrollment Platforms," "UX Research," and "Stakeholder Management."
Interview Preparation: Practice articulating your design process, rationale, and impact using the STAR method for behavioral questions. Prepare to present your portfolio with a focus on storytelling and demonstrating your problem-solving skills.
Company Research: Thoroughly research Oscar Health's mission, values, and recent developments in their marketplace initiatives to articulate your genuine interest and cultural fit during interviews.

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

Product Designer, Marketplace