Senior Product Designer

The role

You will design mission-critical internal tools that power insurance and care operations. You will work with product managers, engineers, and researchers to deliver experiences across a complex ecosystem using AI-assisted workflows.

What you will do

• Independently lead the design process for complex problems.
• Develop a deep understanding of internal users and operational environments.
• Partner with Product and Engineering to define product direction and roadmaps.
• Map complex workflows and systems to identify pain points and opportunities.
• Lead design work from discovery through implementation and iteration.
• Use research, data, hypotheses, and experimentation to evaluate ideas.
• Create prototypes to explore ideas and test assumptions.
• Lead workshops, product-vision activities, and presentations.
• Use Claude and Codex to clarify needs and build realistic prototypes.
• Apply design judgment to AI-generated output.

Required qualifications

• 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.
• 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.

Nice to have

• 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.

Benefits

• Medical, dental, and vision benefits
• 11 paid holidays
• Paid sick time
• Paid parental leave
• 401(k) plan participation
• Life and disability insurance
• Unlimited vacation program
• Paid wellness time and reimbursements

About the company

Oscar is a health insurance company built around a full stack technology platform. It was started in 2012 to create a health insurance company that behaves like a doctor in the family.