Executive Remote Product Designer Jobs (NOW HIRING)

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:

Lucie Health Marketplace is a new all-in-one storefront that will change how Americans shop for healthcare. Lucie connects consumers and brokers to every major individual market plan and a curated menu of ancillary and supplemental products.

As a Product Designer for the Lucie Marketplace, you will design and ship the tools that power how brokers and consumers evaluate and enroll in healthcare coverage. The Lucie ecosystem spans our direct enrollment platform for brokers, the consumer marketplace, and ICHRA tooling. In this role, you will focus heavily on shaping the broker 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 intake systems, enrollment platforms, or CRM tooling. 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 Sr. 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: $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:

• Execute the design process with guidance on complex problems, considering long-term impact with near-term polish within a defined Oscar product area.
• Develop a deep understanding of the users, informing product strategy and solutions throughout the design process.
• Collaborate closely with other product designers, product managers, marketers, brand designers, engineers, researchers and others.
• Follow hypothesis-driven research, prototyping and launching experiments that develop actionable insights.
• Lead or contribute to workshops, vision activities or presentations as needed.
• Exhibit strong craft and interaction design, maintaining a high quality bar for experiences and our design systems.
• Translate the Oscar brand across 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 design contributions across high-performing web, mobile, or internal tool products.
• 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%