Senior Product Designer . Oscar Health

About this role

Senior Product Designer

Oscar Health, New York, USA

Healthcare

Why this work matters

Oscar Health is a for-profit tech-driven health insurer focused on making affordable, accessible healthcare available to underserved Americans via telemedicine and transparent pricing.

View the full listing and apply →Listed 7 Nov 2026Applications are handled by Oscar Health, not by Hard Problems.

About Oscar Health

Oscar Health is a health insurance company built on a full-stack technology platform, founded in 2012 with the goal of creating health insurance that behaves like a doctor in the family. Its Internal Tools design team creates mission-critical products that 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.

The role

This Senior Product Designer position sits within Oscar's Internal Tools design team and reports to a Product Design Director. You would help define and deliver clear, effective experiences across a complex ecosystem of operational products. Your initial product area is determined based on your experience, interests, and Oscar's current needs. The work is operational, workflow-heavy, data-rich, and technically complex, requiring strong systems thinking and comfort with ambiguity.

What you would do

• Lead the design process independently for complex problems, balancing near-term delivery 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, set measurable goals, and contribute to roadmaps.
• Map complex workflows and systems to surface 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 to help teams reach clarity.
• Use AI tools such as Claude and Codex to clarify user and business needs, explore approaches, and identify requirements, risks, and edge cases.
• Use Claude and Codex to build and test realistic interactions, workflows, and front-end prototypes, then apply design judgment to refine their structure, behavior, accessibility, and visual quality.
• 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.
• Collaborate closely with engineers throughout implementation to ensure the shipped experience meets the intended quality bar.
• Contribute to shared design-system components, patterns, and standards, and apply Oscar's brand, accessibility standards, and design principles across product experiences.
• Present work clearly, explain the reasoning behind decisions, and contribute to team critique and design practices.

What they are looking for

• 4 or more 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 or more 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, including working autonomously across complex or ambiguous product areas.
• Experience partnering closely with Product and Engineering to define problems, evaluate solutions, and deliver measurable outcomes.
• Active use of AI-assisted tools such as Claude, Codex, or comparable tools within a product design workflow, including the ability to explain where AI was useful, where it fell short, and how your own judgment shaped the result.
• Strong written, visual, and verbal communication skills.
• Bonus: experience with SaaS, enterprise software, CRM platforms, or operational tools; healthcare, insurance, or other regulated industries; data-dense interfaces, configurable workflows, or multi-role systems; design systems or front-end component libraries; coded or animated prototypes; and interest in accessibility and design ethics in healthcare contexts.

Working arrangements

This position is based in Oscar's New York City office on a hybrid schedule, requiring 3 days in the office per week. Thursdays are a required in-office day for team meetings and events; the other two office days are flexible.

Pay and benefits

The base pay range is $149,040 - $195,615 per year. Full-time employees are also eligible for medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, paid wellness time and reimbursements, company equity grants, and annual performance bonuses. Oscar also offers an unlimited vacation program.

Details

Location : New York, USA

On-site or remote : Hybrid (New York)

Salary : $149,040 - $195,615

Sector : Healthcare

Role : Product design

Seniority : Senior

Organisation : For-profit

This job is listed on the Hard Problems job board, but details come from the employer’s own listing and may have changed — always check the original posting.