Oscar Senior Product Designer at Oscar focusing on internal tools for insurance and care operations. Lead design processes for complex workflows and collaborate with cross-functional teams to deliver effective user experiences.
Responsibilities
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.
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.
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.
Qualification
The ability to translate requirementsActive use of tools such as ClaudeExperience designing SaaS productsExperience in healthcare
Required
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.
