Senior Product Designer, Personalization

Quick Facts

• Role: Senior Product Designer, Personalization
• Team: Clinical Product
• Work model: Remote (open to candidates residing in the Boston, MA area)
• Reports to: Director, Product Design
• Base pay: $149,040.00–$195,615.00 per year

Description

Design trustworthy personalized experiences and tools that help members and teammates understand context, consider recommendations, and take the next useful action. You’ll help build a personalization platform that uses longitudinal member context, real-time behavioral signals, predictive models, and LLMs to forecast what’s likely to happen and determine the most useful next action across web, app, an AI health agent, teammate tools during member conversations, and outbound engagement. Own end-to-end product design—from early vision through quality specifications—while partnering with cross-functional teams on goals, roadmaps, and experimentation.

Responsibilities

• Own the end-to-end design process (from blue sky thinking to quality specs), balancing polish with speed and minimal oversight.
• Develop an expert understanding of users and the business domain to inform product strategy.
• Collaborate closely with product designers, product managers, marketers, brand designers, engineers, researchers, and others.
• Contribute to team goals and strategy by connecting user and business needs.
• Manage stakeholder relationships and drive clarity around decision-making.
• Lead workshops, vision activities, or presentations as needed.
• Bring strong visual and interaction design craft to set a new quality bar and advance design systems.
• Weave the Oscar brand across product experiences.
• Ensure compliance with all applicable laws and regulations.

Requirements

• 6+ years of experience in Product/UX Design.
• Concrete examples of designing and shipping complex interfaces.
• 3+ years managing stakeholders directly.
• Evidence of design contributions across high-performing web, mobile, or internal tool products.
• Experience with user research and prototyping.
• Ability to translate requirements, goals, and research into simple and useful UI.
• Proven record of navigating technical constraints to deliver design solutions.

Benefits

• 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
• Unlimited vacation program, company equity grants, and annual performance bonuses

AI and Accommodation Notes

• AI usage is governed by acceptable-use guidelines for recruiting support.
• Reasonable accommodations are available during the application process upon request.