Glynn Capital
Glynn Capital

Product Designer, Core Insurance

Oscar Health

Oscar Health

Product, Design
Posted on Saturday, November 4, 2023

Hi, we're Oscar. We're hiring a Product Designer, Core Insurance to join our Product Design team.

Oscar is the first health insurance company built around a full stack technology platform and a 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

Our Design Org is a multidisciplinary team that seeks to examine and innovate on the entire health and insurance journey.Our practice is human-centered and data-driven, focusing on empathy, research, and consumer insights. We lead by example and with our values.

As a Product Designer on the Core Insurance team, you will oversee product design within two vital domains: Member & Billing, and Plans & Benefits. These domains focus on our internal users, turning our complex processes into straightforward, potent tools. An aptitude for service design, research, and working with various stakeholders is paramount for any aspirant of this role. A deep-rooted passion for our internal teams and a keen understanding of how upstream actions impact our members is indispensable. This dedication helps push forward Oscar’s mission: making a healthier life accessible and affordable for all.

You will report to a Group Product Design Manager.

Work Location:

Oscar is a blended work culture where everyone, regardless of work type or location, feels connected to their teammates, our culture and our mission.

If you live within commutable distance to our New York City office ( in Hudson Square), our Tempe office (off the 101 at University Ave), or our Los Angeles office (in Marina Del Rey), you will be expected to come into the office at least two days each week. Otherwise, this is a remote / work-from-home role.

You must reside in one of the following states: Alabama, Arizona, California, Colorado, Connecticut, Florida, Georgia, Illinois, Iowa, Kentucky, Maryland, Massachusetts, Michigan, New Hampshire, New Jersey, New Mexico, New York, North Carolina, Ohio, Oregon, Pennsylvania, Rhode Island, Tennessee, Texas, Utah, Virginia, Washington, or Washington, D.C. Note, this list of states is subject to change. #LI-Remote

Pay Transparency:

The base pay for this role is $131,200-$172,200 per year. You are also eligible for employee benefits, company equity grants, participation in Oscar's unlimited vacation program and annual performance bonuses.


  • 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


  • 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

This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here.

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives..

Pay Transparency:

Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience.

Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

Reasonable Accommodation:

Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team (accommodations@hioscar.com) to make the need for an accommodation known.