Product Designer, Marketplace at Oscar Health

📍 Job Overview

Job Title: Product Designer, Marketplace

Company: Oscar Health

Location: San Francisco, California, United States

Job Type: Full-Time

Category: Product Design / UX Design

Date Posted: June 4, 2026

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

Remote Status: Fully Remote (San Francisco, CA based)

🚀 Role Summary

Design and deliver user-centric digital products for Oscar Health's Lucie Health Marketplace, a new platform revolutionizing healthcare shopping.
Focus on creating intuitive and efficient experiences for brokers and consumers navigating complex healthcare enrollment and ancillary product selection.
Collaborate cross-functionally with Product Management, Engineering, Research, Data Science, and Operations to drive features from initial concept through high-fidelity delivery.
Leverage modern design workflows, including AI-assisted tools, to enhance design-to-engineering processes and maintain a high quality bar.

📝 Enhancement Note: This role is situated within a dynamic and innovative healthcare technology company, specifically focusing on a new marketplace initiative. The emphasis on designing complex intake, enrollment, and CRM-like tooling indicates a need for a designer experienced in B2B and B2C platforms dealing with intricate data and user flows. The mention of AI-assisted tools suggests a forward-thinking design team embracing technological advancements.

📈 Primary Responsibilities

Execute the end-to-end product design process, including user research, wireframing, prototyping, high-fidelity visual design, and user testing, with a focus on the Lucie Health Marketplace, particularly the broker experience.
Develop a deep understanding of user needs, pain points, and workflows for both brokers and consumers to inform product strategy and deliver impactful solutions.
Collaborate closely with Product Managers to define product requirements, user stories, and feature roadmaps, ensuring alignment with business objectives.
Partner with Engineers to translate design specifications into functional, high-quality user interfaces, providing clear documentation and design assets.
Work with UX Researchers to plan and conduct user research, analyze findings, and iterate on designs based on data-driven insights and hypothesis-driven experimentation.
Maintain and contribute to Oscar Health's design system, ensuring consistency, scalability, and adherence to brand guidelines across all product touchpoints.
Translate complex healthcare insurance concepts and regulatory requirements into simple, accessible, and user-friendly interfaces.
Actively participate in design critiques, workshops, and vision-setting activities to foster a collaborative and innovative design culture.
Ensure designs comply with all applicable healthcare industry regulations and accessibility standards.

📝 Enhancement Note: The responsibilities highlight a blend of strategic thinking and hands-on execution. The emphasis on "long-term impact with near-term polish" suggests a need for designers who can balance immediate delivery needs with scalable, future-proof solutions. The mention of "hypothesis-driven research" and "launching experiments" points to an agile and data-informed design approach.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design, Human-Computer Interaction, Graphic Design, or a related field, or equivalent practical experience, is highly recommended for foundational understanding.

Experience: Minimum of 4+ years of professional experience in Product Design, UX Design, or a similar role, with a strong portfolio showcasing complex web and mobile interface design. At least 2 years of experience directly managing and influencing stakeholders is critical.

Required Skills:

Product Design & UX: Proven ability to design user-centered interfaces for web and mobile applications, demonstrating a strong understanding of UX principles, user flows, and information architecture.
Visual & Interaction Design: High craft in visual design, including typography, color theory, and layout, coupled with expertise in interaction design to create engaging and intuitive user experiences.
Prototyping & Wireframing: Proficiency in creating wireframes, interactive prototypes, and user flow diagrams using industry-standard tools (e.g., Figma).
Stakeholder Management: Demonstrated ability to effectively communicate design decisions, gather feedback, and manage expectations with cross-functional stakeholders, including product managers, engineers, and business leaders.
Design Systems: Experience working with and contributing to design systems to ensure consistency and scalability across product features.
Problem-Solving: Ability to translate complex requirements, user needs, and technical constraints into elegant and effective design solutions.

Preferred Skills:

Healthcare Industry Experience: Familiarity with the healthcare insurance landscape, including enrollment processes, regulatory compliance, and user needs specific to this sector.
Complex System Design: Experience designing intake systems, enrollment platforms, or CRM tooling that handle significant data complexity and multi-step user journeys.
AI-Assisted Design Tools: Comfort and experience leveraging AI tools (e.g., Claude Code) to enhance design workflows and accelerate the design-to-engineering handoff.
User Research: Experience conducting user research, usability testing, and synthesizing findings to inform design decisions.
Storytelling: Ability to effectively communicate design rationale and user insights through compelling presentations, animated prototypes, or detailed user flow diagrams.
Accessibility & Design Ethics: Knowledge of accessibility standards (WCAG) and a commitment to ethical design practices, particularly within the sensitive healthcare domain.

📝 Enhancement Note: The "Bonus points" section strongly suggests that experience with complex intake/enrollment systems, healthcare, and AI tools are highly valued. The emphasis on stakeholder management for 2+ years indicates this role requires a degree of seniority and influence. The requirement for "2+ concrete examples of designing and shipping complex web and mobile interfaces" means candidates must be prepared to present specific case studies.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

Case Studies: A portfolio featuring at least 2-3 detailed case studies showcasing the end-to-end design process for complex web and/or mobile interfaces. Each case study should clearly articulate the problem, your role, the design process, key decisions, challenges faced, and the final outcome/impact.
Process Documentation: Demonstrate your approach to user research, ideation, wireframing, prototyping, visual design, and user testing within your case studies. Highlight how you translated user needs and business requirements into design solutions.
System Interaction Design: Showcase examples of designing for complex systems, such as enrollment platforms, intake forms, or CRM-like tooling, emphasizing user flows, data management, and error handling.
Visual Craft & Design Systems: Include high-fidelity mockups and examples of how you've applied visual design principles and adhered to or contributed to a design system.

Process Documentation:

Workflow Design: Examples of how you've mapped out and optimized user workflows for complex tasks, demonstrating an understanding of user journey mapping and process efficiency.
Implementation & Handoff: Showcase your methods for preparing design assets and specifications for engineering handoff, including documentation and collaboration practices.
Data-Informed Iteration: Provide evidence of how you've used user feedback, data analytics, or A/B testing results to iterate on and improve designs.

📝 Enhancement Note: The emphasis on "complex web and mobile interfaces" and "complex intake systems, enrollment platforms, or CRM tooling" means the portfolio should clearly demonstrate the ability to handle intricate user journeys and data structures, not just simple UI elements. Candidates should be prepared to discuss their process for managing ambiguity and technical constraints.

💵 Compensation & Benefits

Salary Range: $123,372.00 - $161,925.75 per year. This range is based on the provided information and reflects a San Francisco, California market rate for a Product Designer with 4+ years of experience in a tech-focused healthcare company. Factors such as specific skills, interview performance, and overall candidate qualifications will influence the final offer within this band.

Benefits:

Comprehensive Health Coverage: Medical, dental, and vision insurance plans.
Financial Wellness: 401(k) plan participation, life insurance, and disability insurance.
Work-Life Balance: Unlimited vacation program, paid sick time, paid parental leave, and 11 paid holidays.
Wellness & Development: Paid wellness time, wellness reimbursements, and annual performance bonuses.
Equity & Growth: Company equity grants, offering potential for long-term financial reward.

Working Hours: Standard full-time work hours (approximately 40 hours per week), with flexibility expected for project deadlines and cross-functional collaboration, especially given the remote nature of the role.

📝 Enhancement Note: The salary range is explicitly provided. The benefits list is extensive, with particular emphasis on work-life balance (unlimited vacation, generous paid leave) and long-term incentives (equity, bonuses), which are attractive aspects for experienced professionals. The mention of AI guidelines suggests a modern approach to technology integration within the company's operations.

🎯 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. The Lucie Health Marketplace initiative positions them to expand their reach and offerings in a competitive landscape.

Company Size: Oscar Health is a significant player in the health insurance tech space, indicating a mid-to-large-sized organization with established processes but retaining an innovative and agile spirit. This size typically allows for meaningful impact while providing resources and structure.

Founded: Founded in 2012, Oscar Health has a history of innovation, aiming to redefine health insurance through technology and a focus on member experience. This founding principle likely permeates its current culture.

Team Structure:

The Product Design team is led by a Sr. Director, Product Design.
This role will work closely with a Senior Product Designer focused on the Lucie Marketplace.
Collaboration will be extensive with Product Managers, Engineers, Researchers, Data Scientists, and Operational Stakeholders.

Methodology:

Data-Driven Design: Emphasis on hypothesis-driven research, experimentation, and using data to inform product decisions and measure impact.
Agile Development: Likely operates within an agile framework, requiring close collaboration between design, product, and engineering throughout the development lifecycle.
User-Centricity: A core philosophy, driven by a "relentless focus on serving our members" and understanding user needs deeply.
AI Integration: Embracing modern workflows, including the use of AI-assisted tools to streamline design and development processes.

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

📝 Enhancement Note: Oscar Health positions itself as a technology-first health insurance company. The culture likely values innovation, data-driven decision-making, and a proactive approach to problem-solving, especially within the complex healthcare domain. The mention of "Lucie Health Marketplace" signifies a key strategic growth area for the company.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a Mid-Senior level within Product Design. It requires significant autonomy in execution, strong stakeholder management skills, and the ability to contribute to product strategy. It's a step towards leading design initiatives independently or mentoring junior designers.

Reporting Structure: The Product Designer will report to the Sr. Director, Product Design, and will work closely with a Senior Product Designer on the Lucie Marketplace team. This dual reporting/collaboration structure allows for guidance and mentorship while fostering independence.

Operations Impact: The Product Designer will have a direct impact on the success of the Lucie Health Marketplace by shaping how consumers and brokers interact with healthcare plans and ancillary products. Successful design translates to improved user acquisition, retention, operational efficiency, and ultimately, revenue growth for Oscar Health.

Growth Opportunities:

Skill Specialization: Deepen expertise in designing for complex marketplaces, healthcare tech, or enterprise-level tooling.
Leadership Development: Potential to lead design efforts for specific features or product areas, mentor junior designers, and contribute to the evolution of the design system.
Cross-Functional Exposure: Gain in-depth experience working with diverse teams, understanding business strategy, and contributing to product vision.
Industry Advancement: Develop a strong portfolio and resume with experience in a leading health tech company, opening doors to senior and lead design roles.
Continuous Learning: Opportunities to attend industry conferences, workshops, and leverage AI tools for professional development.

📝 Enhancement Note: The role offers a clear path for growth from a hands-on individual contributor to a more strategic and potentially leadership-oriented position within the design organization. The focus on a new, high-impact initiative like the Lucie Marketplace provides significant visibility and opportunity for professional development.

🌐 Work Environment

Office Type: This is a fully remote position, allowing for flexibility in work location within San Francisco, CA. While currently remote, the company notes that future work models might adapt, potentially including hybrid presence at a hub office.

Office Location(s): The role is open to candidates residing in San Francisco, CA. This indicates a strong presence and potential future hub for Oscar Health in this major tech and innovation center.

Workspace Context:

Remote Flexibility: Embrace the autonomy and flexibility of remote work, managing your own schedule to meet project demands.
Digital Collaboration: Reliance on digital communication and collaboration tools (e.g., Slack, Zoom, Figma) to connect with team members and stakeholders.
Technology Integration: Access to modern design tools and AI-assisted technologies to enhance productivity and workflow efficiency.
Team Interaction: Opportunities for regular virtual team meetings, design critiques, and cross-functional syncs to foster connection and collaboration.

Work Schedule: A standard full-time schedule is expected, approximately 40 hours per week. The remote nature offers flexibility, but effective time management is crucial to balance personal needs with project deadlines and collaborative sessions, especially with teams in different time zones.

📝 Enhancement Note: The remote-first approach in San Francisco, CA, caters to talent in a major tech hub. The mention of potential future hybrid models suggests a dynamic work environment that may evolve, requiring adaptability. Emphasis on digital collaboration tools is standard for remote roles.

📄 Application & Portfolio Review Process

Interview Process:

Application Submission: Submit resume and portfolio through the Oscar Health careers portal.
Initial Screening: A recruiter will review applications to assess qualifications and alignment with role requirements.
Portfolio Review & Design Challenge: Candidates will likely be asked to present their portfolio, focusing on 2-3 key case studies that demonstrate experience with complex interfaces and stakeholder management. A design challenge or exercise may be administered to assess problem-solving skills and design approach.
Hiring Manager & Team Interviews: Interviews with the Sr. Director of Product Design, Senior Product Designer, and potentially cross-functional partners (Product Managers, Engineers) to evaluate design craft, collaboration style, strategic thinking, and cultural fit.
Final Round: Potentially a final interview with senior leadership.

Portfolio Review Tips:

Highlight Complexity: Showcase projects that involved intricate user flows, data management, or complex decision-making processes (e.g., enrollment, intake, CRM).
Process-Oriented: Clearly articulate your design process for each case study, emphasizing how you identified user needs, iterated on solutions, and collaborated with stakeholders.
Quantify Impact: Whenever possible, include metrics or qualitative feedback that demonstrate the positive impact of your design solutions on users and business goals.
Showcase Collaboration: Discuss how you managed stakeholder expectations, incorporated feedback, and worked effectively with engineering and product teams.
Emphasize AI Tools: If relevant to your projects, briefly mention how you leveraged AI-assisted tools to enhance your workflow.

Challenge Preparation:

Understand the Domain: Familiarize yourself with Oscar Health's mission, the Lucie Health Marketplace concept, and the general landscape of health insurance technology.
Practice Problem-Solving: Be ready to tackle a design problem related to user onboarding, information architecture for complex data, or improving conversion rates within a marketplace context.
Articulate Your Process: Focus on explaining your thought process, decision-making rationale, and how you would approach user research and validation for the given challenge.
Consider Constraints: Think about potential technical, business, and regulatory constraints inherent in the healthcare space.

📝 Enhancement Note: The interview process is designed to assess both design craft and the ability to navigate complex stakeholder environments. Candidates should be prepared to defend their design decisions with data and user insights, and demonstrate how they can contribute to a fast-paced, innovative team.

🛠 Tools & Technology Stack

Primary Tools:

Figma: The primary tool for UI design, wireframing, prototyping, and collaboration. Proficiency is essential.
AI-Assisted Design Tools: Explicitly mentioned is Claude Code, alongside other potential AI tools for code generation, content creation, or design exploration. Familiarity with these is a plus.

Analytics & Reporting:

While not explicitly listed, experience with analytics platforms (e.g., Google Analytics, Amplitude, Mixpanel) for understanding user behavior and measuring design impact is highly beneficial.

CRM & Automation:

Experience designing for or within CRM systems (e.g., Salesforce, HubSpot) or similar complex internal tools is a significant advantage, given the role's focus on broker and enrollment platforms.
Understanding of workflow automation principles as they apply to user journeys and operational efficiency.

📝 Enhancement Note: The explicit mention of Figma and AI-assisted tools like Claude Code indicates the company's modern tech stack and emphasis on efficiency. Experience with enterprise-level tools like CRMs is a strong indicator of suitability for the complex systems this role will design.

👥 Team Culture & Values

Operations Values:

Member-Centricity: A deep commitment to understanding and serving the needs of Oscar Health members, driving every design decision with user empathy.
Innovation & Agility: A culture that encourages experimentation, embraces new technologies (like AI), and moves quickly to adapt to market changes.
Collaboration: Strong emphasis on cross-functional teamwork, open communication, and shared ownership of product success.
Data-Driven Decision Making: Reliance on research, analytics, and hypothesis testing to validate design choices and measure impact.
Humility & Determination: A blend of being genuinely inquisitive and open to learning, coupled with the drive to see complex projects through to completion.

Collaboration Style:

Cross-Functional Integration: Designers work hand-in-hand with Product Managers, Engineers, Researchers, and Data Scientists as integrated members of product teams.
Iterative Feedback: Regular opportunities for design critiques, sprint reviews, and feedback sessions to refine designs collaboratively.
Knowledge Sharing: An environment that encourages sharing insights, best practices, and learnings across the design and product organizations.

📝 Enhancement Note: The company values highlight a forward-thinking, user-focused, and collaborative environment. The mention of "humble yet determined" suggests a team that values both learning and execution.

⚡ Challenges & Growth Opportunities

Challenges:

Navigating Healthcare Complexity: Designing for the intricate and regulated healthcare industry requires a deep understanding of user needs, compliance, and technical constraints.
Balancing Stakeholder Needs: Effectively managing diverse stakeholder expectations and priorities while advocating for user-centered design.
Driving Adoption of New Marketplace: Ensuring the Lucie Health Marketplace is intuitive and valuable for both brokers and consumers to drive adoption and achieve business goals.
Rapid Iteration & Execution: Operating in a fast-paced environment that requires delivering high-quality designs quickly and iterating based on feedback and data.
Leveraging AI Tools Effectively: Integrating AI-assisted tools into the design workflow without compromising design quality or user experience.

Learning & Development Opportunities:

Specialized Design Skills: Opportunities to hone skills in designing for marketplaces, complex B2B/B2C platforms, and regulated industries.
Mentorship: Guidance from experienced Senior Product Designers and leadership within a growing design organization.
Industry Exposure: Gaining valuable experience in the rapidly evolving health tech sector.
Tool Proficiency: Becoming adept with cutting-edge design and AI tools used in modern product development.

📝 Enhancement Note: The primary challenge lies in translating the complexity of healthcare insurance and marketplace dynamics into user-friendly designs. Growth opportunities are tied to mastering these complexities and contributing to strategic product initiatives.

💡 Interview Preparation

Strategy Questions:

"Describe a time you designed a complex intake or enrollment system. What were the key challenges, and how did you address them?" (Focus on process, user needs, and stakeholder management.)
"How do you balance speed of execution with design quality and long-term impact?" (Highlight your approach to prototyping, iteration, and scalable design.)

Company & Culture Questions:

"What interests you about Oscar Health and our mission to change healthcare?" (Research Oscar's mission, values, and recent initiatives.)
"How do you approach working with product managers and engineers to ensure successful product delivery?" (Emphasize your collaborative style and communication strategies.)

Portfolio Presentation Strategy:

Structure Your Narrative: For each case study, clearly define the problem, your specific role and contributions, the design process undertaken, key decisions, challenges, and the measurable outcomes.
Focus on Impact: Quantify your impact with data (e.g., conversion rates, task completion times, user satisfaction scores) or strong qualitative insights.
Demonstrate Collaboration: Explain how you collaborated with product managers, engineers, and other stakeholders, and how you incorporated their feedback.
Highlight Complexity: Choose projects that best showcase your ability to handle complex user flows, intricate data, and challenging technical constraints.
Showcase Craft: Ensure your visual design and interaction design are polished and clearly communicated through your presentation materials.

📝 Enhancement Note: Candidates should prepare to articulate their design process with specific examples, demonstrating how they apply user-centered principles in a complex, regulated industry while managing multiple stakeholders.

📌 Application Steps

To apply for this Product Designer position:

Submit your application through the Oscar Health careers portal, including your resume and a link to your online portfolio.
Portfolio Customization: Tailor your portfolio to highlight at least two concrete examples of designing and shipping complex web and mobile interfaces, ideally showcasing experience with intake, enrollment, or CRM-like tooling.
Resume Optimization: Ensure your resume clearly details your 4+ years of Product/UX Design experience and explicitly mentions your 2+ years of stakeholder management. Use keywords from the job description like "Product Design," "UX Design," "Complex System Design," "Figma," and "Stakeholder Management."
Interview Preparation: Practice articulating your design process, decision-making rationale, and collaboration strategies for common Product Design interview questions. Be ready to present your portfolio case studies concisely and effectively.
Company Research: Thoroughly research Oscar Health's mission, values, and the Lucie Health Marketplace initiative. Understand their approach to technology and member experience to articulate your interest and cultural fit.

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

Product Designer, Marketplace