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.