Senior Product Designer, Oscar Health

• 4+ years of experience in Product Design, UX Design, or a related field
• At least two examples of designing and shipping complex web, mobile, SaaS, or internal-tool experiences
• 2+ years owning relationships with cross-functional stakeholders
• A strong portfolio demonstrating product thinking, systems thinking, interaction design, and visual craft
• Experience owning product design work from problem definition through launch and iteration
• Experience working autonomously across complex or ambiguous product areas
• Experience partnering closely with Product and Engineering to define problems, evaluate solutions, and deliver measurable outcomes
• The ability to translate requirements, business goals, research, and technical constraints into clear and useful product experiences
• Active use of tools such as Claude, Codex, or comparable AI-assisted tools within a product design workflow
• Comfort using AI-assisted development tools to create realistic prototypes, even if you do not write production code by hand
• Examples of using AI to improve the speed, fidelity, or quality of product exploration and delivery
• The ability to explain where AI was useful, where it was insufficient, and how your own judgment shaped the result
• Strong written, visual, and verbal communication skills

Desirable

• Oscar’s Internal Tools design team creates the mission-critical products that power our insurance and care operations
• These tools support teams across Clinical, Core Insurance, and Network as they manage complex workflows involving claims, risk adjustment, provider networks, clinical care, and other essential business functions
• As a Senior Product Designer, you will help define and deliver clear, effective experiences across this ecosystem
• You will work closely with product managers, engineers, researchers, data partners, clinicians, operational teams, and other designers to understand complex problems, identify opportunities, and take solutions from discovery through delivery
• The work is operational, workflow-heavy, data-rich, and technically complex
• It requires strong systems thinking, comfort with ambiguity, and the ability to connect decisions across users, workflows, and products
• Your initial product area will be determined based on your experience, interests, and Oscar’s current needs
• Oscar is building an AI-enabled design practice
• You will use approved tools such as Claude and Codex to clarify problems, explore workflows, identify risks and edge cases, and create realistic prototypes earlier in the design process
• You will bring validated directions into Figma for complete state coverage, design-system alignment, and production readiness
• You will also help the broader team develop effective and responsible ways of working with AI
• This role reports to a Product Design Director
• Independently lead the design process for complex problems, balancing immediate delivery and polish with a coherent long-term direction
• Develop a deep understanding of internal users, their goals, and the operational environments in which they work
• Partner with Product and Engineering to define product direction, identify opportunities, establish measurable goals, and contribute to roadmaps
• Map complex workflows and systems to identify pain points, dependencies, duplication, and opportunities for simplification
• Lead design work from early discovery and concept development through detailed interaction design, implementation, and iteration
• Use research, data, hypotheses, and experimentation to evaluate ideas and improve product direction
• Create prototypes that help teams explore ideas, test assumptions, and build confidence in a proposed solution
• Lead workshops, product-vision activities, and presentations when they help teams reach clarity
• Use Claude and Codex to clarify user and business needs, explore possible approaches, and identify requirements, risks, and edge cases
• Use Claude and Codex to build and test realistic interactions, workflows, and front-end prototypes
• Apply strong design judgment to AI-generated output, refining its structure, behavior, accessibility, and visual quality
• Partner with engineers to determine which prototypes, patterns, or components can be carried into production
• Use Figma to ensure validated concepts have complete states, follow shared patterns, and are ready for implementation
• Document and share useful prompts, workflows, prototypes, and lessons that improve how the broader design team uses AI
• Use AI responsibly and in accordance with Oscar’s privacy, security, and member-data requirements
• Collaborate closely with engineers throughout implementation to ensure the shipped experience meets the intended quality bar
• Navigate technical constraints without losing sight of user needs, product quality, or long-term scalability
• Contribute to a consistent and scalable experience across Oscar’s internal products
• Use and improve shared design-system components, patterns, and standards
• Apply Oscar’s brand, accessibility standards, and design principles across product experiences
• Present work clearly, explain the reasoning behind decisions, and invite feedback at the appropriate stages
• Contribute to team critique, design practices, and the growth of the broader Product Design organization
• Compliance with all applicable laws and regulations
• Other duties as assigned