Senior Product Designer

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:

As a Senior Product Designer on the Network Pillar, you will partner closely with product managers, engineers, and operational stakeholders, to design and ship tools that power how Oscar evaluates, manages, and configures its provider network. You will be central to improving operational workflows and decision-making, ensuring internal teams can efficiently assess network adequacy, performance, and provider relationships. The Network Pillar is shaping a suite of new products that bring critical capabilities in-house, helping Oscar ensure its network of providers and services remains comprehensive, high-quality, and accessible to members nationwide. This designer will play a key role in shaping the tools that enable Oscar’s teams to maintain and grow strong partnerships with providers, all while driving a consistent, scalable, and intuitive experience across the company’s network management ecosystem.

The ideal candidate brings strong systems thinking, experience designing SaaS or internal tools, and the ability to work autonomously from discovery through delivery—balancing speed, clarity, and user empathy across complex technical domains.

You will report into the Senior Director, Product Design.

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:

• Own the end-to-end design process (from blue sky thinking to quality specs), balancing polish with speed to execution, with minimal oversight, across various Oscar surfaces.  
• Develop an expert understanding of the users and business domain, informing product strategy and solutions throughout the design process.  
• Collaborate closely with other product designers, product managers, marketers, brand designers, engineers, researchers and others. 
• Play a large role in defining team goals and strategy, connecting the dots between user and business needs.  
• Manage stakeholder relationships, driving towards clarity around decision making.  
• Lead workshops, vision activities or presentations as needed.
• Bring strong visual and interaction design craft, setting a new quality bar for experiences, the wider team, and our design systems.
• Weave the Oscar brand across product experiences.
• Compliance with all applicable laws and regulations. 
• Other duties as assigned.

Requirements:

• 6+ years of experience in Product/UX Design. 
• Concrete examples of designing and shipping complex interfaces. 
• 3+ years managing stakeholders directly. 

Bonus points:

• Experience with the healthcare space.
• Storytelling techniques such as animated prototypes or user flow diagrams.  
• Interest in design ethics, accessibility, and other topics relevant to the healthcare space.
• Genuine and inquisitive, humble yet determined.
• Evidence of design contributions across high-performing web, mobile, or internal tool products.
• Excitement in elevating team through thoughtful coaching and collaboration.
• Proven record of navigating technical constraints to deliver design solutions.   
• Experience with user research and prototyping. 
• Ability to translate requirements, goals, and research into simple and useful UI.