Senior Product Designer

Join Oscar's Internal Tools design team as a Senior Product Designer. You will define and deliver effective experiences across our mission-critical products that power insurance and care operations. Collaborate with cross-functional teams, map complex workflows, and lead the design process from discovery to delivery. Use AI-assisted tools to enhance your design workflow and contribute to a consistent and scalable experience across Oscar's internal products.

• 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, and partner with Product and Engineering to define product direction.
• Use research, data, hypotheses, and experimentation to evaluate ideas and improve product direction, and create prototypes that help teams explore ideas, test assumptions, and build confidence in a proposed solution.

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