Hi, we're Oscar. We're hiring a Senior Product Designer to join our Product Design team.

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.

About the role:

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.

Work Location:

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. #LI-Hybrid

Pay Transparency:

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.

Responsibilities:

• 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.

Requirements:

• 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.

Bonus points:

• Experience designing SaaS products, enterprise software, CRM platforms, operational tools, or similarly complex applications.
• Experience in healthcare, insurance, financial services, or another regulated industry.
• Experience designing data-dense interfaces, configurable workflows, permissions, or multi-role systems.
• Experience simplifying fragmented products, workflows, or product ecosystems.
• Experience contributing to or working closely with a design system or front-end component library.
• Experience creating realistic or coded prototypes.
• Familiarity with front-end concepts such as components, states, responsive behavior, and accessibility.
• Experience planning and conducting customer interviews, usability testing, or other lightweight research.
• Experience using animated prototypes, working software, or user-flow diagrams to communicate a product direction.
• Experience contributing reusable prompts, patterns, components, or workflows to a broader team.
• Experience designing AI-powered products, including considerations around transparency, uncertainty, user control, and trust.
• Interest in accessibility, design ethics, and the responsibilities involved in designing healthcare products.
• A genuine and inquisitive working style, with humility, determination, and openness to feedback.