Events  Deals  Jobs 
    Sign in  
Oscar Health // health insurance
Design, Full Time    New York City, United States    Posted: Monday, August 01, 2022
Apply To Job

Hi, we're Oscar. Were hiring a Product Design Director to join our Product Design Team. 

Were changing how health insurance works. Our goal is to make health insurance simple, transparent, & human. We need your help to do so. We brought together leaders from top technology, service, & healthcare companies to work side by side to disrupt health insurance. The result? Better people, better ideas, & better health care.

About the role:

Were hiring a design leader to manage & guide Oscars SaaS product design team. This team of talented designers & design managers is focused on building a unified, user-centric, & flexible platform to tackle complex problems across our core insurance business. Youll work across multiple products & platforms to deliver meaningful results for our internal & enterprise users, as well as the members & providers they serve.

You will report to the VP of Product Design. This is a hybrid role. You will work part of the time in the New York City office & part of the time work-from-home/remote. #LI-Hybrid


  • Serve as a strategic partner to shape the future of Oscars SaaS products in partnership with Product Management using your vantage point to spot opportunity & steer teams in the right direction. 
  • Organize initiatives to further our continuous discovery & solidify the foundation our teams are building upon. 
  • Evaluate the effectiveness of our work, & recommend adjustments to our team & process. 
  • Socialize & evangelize the design teams work across cross-functional teams.
  • Work closely with the VP to align to the company mission & vision & create business cases for design initiatives.
  • Manage & develop a talented team of product designers & managers across a range of product design skill sets.
  • Lead with empathy, transparency, & inclusivity, with a focus on ongoing feedback & keeping a finger on the pulse of the teams needs.  
  • Own the teams performance, resourcing, prioritization, well-being, & culture & serve as a key driver of delivering innovation.
  • Lead design-driven greenfield work involving key team members & stakeholders to discover near-term & long-term areas of opportunity.
  • Define & improve processes, unblocking team members to do their best work.
  • Effectively communicate the teams progress & accomplishments, as well as need & challenges, to company leaders.


  • 5+ years of leading & directly managing designers & managers, preferably in a SaaS environment.
  • 10+ years of experience in product design, building & shipping applications or software across platforms.
  • Experience in a design leadership role, directly contributing & leading people, process, & product strategies. 
  • Ability to solve difficult problems through past work experience & case studies.
  • Experience shaping design direction & strategic thinking, identifying goals & opportunities, & making impact-based decisions.
  • Engaging presentation skills & the ability to tell compelling stories to cross-functional audiences.
  • Ability to analyze & deconstruct complex systems into smaller bits & pieces.
  • Well-developed design & research skills, ability to give feedback & mentor designers in growing their technical skill-sets.

Bonus points:

  • Experience within the healthcare space.
  • Experience working on large, complex projects across multiple teams.
  • Experience working on SaaS products will help, but a strong interest in connecting. complex systems in a way that creates compelling user experiences is even better.

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

Life at Oscar: 

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 & find both belonging & support. We're on a mission to change health care -- an experience made whole by our unique backgrounds & perspectives.

We aim to make health care affordable & accessible for all, & apply this same vision to our perks & benefits, including: medical benefits, generous paid-time off, paid parental leave, retirement plans, company social events, stocked kitchens, wellness programs, & volunteer opportunities.

Reasonable Accommodation:

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

To protect the health & safety of our employees, we require any employee conducting in-person work* to be fully vaccinated against COVID-19 by their start date. If you are unable to be vaccinated due to medical or protected religious reasons, please reach out to our Benefits team at to submit an accommodations request.

*Note: In-person work includes: employees required to work from our offices, employees conducting sales work in the field & employees conducting at-home or in-person visits with members.

Apply To Job
© 2022 GarysGuide      About    Feedback    Press    Terms