Remote Associate Product Designer Jobs in Massachusetts

Hi, we're Oscar. We're hiring a 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 Product Designer for the Lucie Marketplace, you will design and ship the tools that help employers easily manage health plan contributions for their employees. The Lucie ecosystem spans our direct enrollment platform for brokers, the consumer marketplace, and ICHRA tooling. In this role, you will focus on shaping the ICHRA experience, contributing to the other areas as needed. Partnering closely with a Senior Product Designer in this space, you will collaborate cross-functionally with product managers, engineers, research, data and operational stakeholders to take features from discovery through delivery while driving a consistent, scalable, and intuitive experience across the entire Lucie suite.

The ideal candidate brings a strong visual design portfolio and a proven track record of designing complex enterprise software, data-intensive platforms, or workforce management tools. You can work autonomously across multiple technical domains from initial research through high-fidelity delivery, consistently balancing execution speed with deep user empathy. Additionally, you thrive in a modern workflow and are comfortable leveraging AI-assisted tools like Claude Code alongside Figma to streamline the design-to-engineering process. 

You will report into the SVP, Product, Design, Data.

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: $$123,372.00 - $161,925.75 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities:

• Define the experiences for Oscar's users, enabling a wide array of use cases that all contribute towards providing exceptional care in support of Oscar's mission to make a healthier life affordable and accessible to all
• Become an expert on the product's users and their journeys, advocating their needs and pain points to the larger org 
• Own the design process and partner closely with cross-functional peers like product managers, tech leads, engineers, data scientists and business stakeholders to drive clarity around strategy and alignment on solutions  
• Collaborate with other product designers across the organization with feedback during critiques and thoughtful contributions to the design team at large 
• Perform user research and usability testing with a clear focus on generating actionable insights to drive informed design decisions.
• Design visually compelling experiences for all users and contribute to the Oscar design language system (Anatomy)
• Bring the Oscar brand to life in our product experiences
• Compliance with all applicable laws and regulations 
• Other duties as assigned

Requirements:

• 4+ years of experience in Product/UX Design
• 2+ concrete examples of designing and shipping complex web and mobile interfaces 
• 2+ 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 contribution to internal tools, system workflows, and power-user interfaces
• 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