Senior Product Designer - Personalization

Hi, we're Oscar. We're hiring a Senior Product Designer, Personalization to join our Clinical Product 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:

Design trustworthy personalized experiences that help members and Oscar teammates understand context, consider recommendations, and take the next useful action. 

A Senior Product Designer explores, designs, shapes and reimagines the vision for tools that empower Oscar to deliver best in class care to our Members. The role generates and explores ideas, designs, with hypothesis based testing and experimentation producing high quality features. The Senior Product Designer plays an active role in defining the vision for the product area they support, partnering with cross-functional colleagues to define goals, contribute to roadmaps, identify opportunities, and imagine the path towards a future vision.  

As a Senior Product Designer, personalization, you will help build Oscar Health’s personalization platform, using longitudinal member context, real-time behavioral signals, predictive models, and LLMs to forecast what is likely to happen for each member and identify the most useful next action. We combine longitudinal member context with real-time behavioral signals to forecast what is likely to happen for a member and determine the most useful next action for the member to engage across web and app, our member facing health AI agent (Oscar), tools used by Oscar teammates during member conversations, and intentional outbound engagement. The work includes predictive modeling; creating a catalogue of action and journey options to engage members with; recommendation and ranking systems; experimentation and measurement; and practical use of AI and LLMs to interpret context, support recommendations, and generate tailored experiences. We are looking for people who have built and operated personalization, recommender, ranking, predictive-modeling, search, decisioning, or applied-AI systems at meaningful scale. This is a unique opportunity to build an advanced platform leveraging the latest capabilities at an AI-forward company that owns its technology stack, with tangible benefits for members’ health and lives.

You will report into the Director, Product Design.

Work Location: This is a remote position, open to candidates who reside in: Boston, MA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

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 designing and shipping search, recommendation, AI-assisted, or complex decision-support interfaces.
• 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.

Travel Required

• Up to 5%