Product Designer

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

• 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.

• 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.

• This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule.
• The base pay for this role is: $149,040.00 - $195,615.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.