Head of Product Design

New York, New York, United States

Full Time Executive-level / Director
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Posted 2 weeks ago

Hi, we're Oscar. We're hiring a new Head of Product Design to join our Product team in our NYC office.

Oscar is a technology-driven, consumer-focused health insurance startup founded in 2012 and headquartered in New York City. Our goal is to make health insurance simple, transparent, and human. We need your help to do so.

Our Product Design org is a multidisciplinary team that examines the end-to-end journey and considers the design of systems to be as important as the artifacts we make. Our practice is human-centered, our work is rooted in empathy and research, and we lead by example and with our values.

As our new Head of Product Design, you will contribute to the future vision of our products and lead a world-class team of 20 designers, researchers, and managers. Everyday, you will motivate our team by nurturing a culture of creativity and inspire everyone with your thoughtful leadership. You will ensure your team generates breakthrough ideas and ultimately ship beloved experiences. You will inspire everyone with your thoughtful leadership. You will prioritize user advocacy, accessibility, and inclusion in this fast-paced, high-growth environment.

This role reports to our SVP of Product in our NYC office.


  • Lead our Product Design & Design Research functions across numerous product areas

  • Advocate for design and user experience by helping leaders across the business make evidence-based decisions

  • Mentor and coach the Design team in their relentless pursuit of product and design excellence

  • Empower Design to influence product strategy through vision work and proposals for new features / products

  • Invest in continuous improvement by evolving our processes and how we work with partners

  • Align Product Design with the strategy of the company, grow the team’s ability to connect design decisions to business impact

  • Work alongside Product Management and Engineering leadership to define the long-term vision for our products, and the strategies and roadmaps to see it through

  • Maintain an integrated outlook of all the products, individually and as a whole. Everything we design should take into account current particular needs as well as the longer term vision for the product

We value leaders from diverse backgrounds and will consider candidates with different types of education and relevant professional experiences in determining qualification. If you feel qualified, please apply. Your experiences and your demonstrated skill sets are far more important than your level or industry expectations.

  • 10+ years of relevant industry experience

  • 5+ years leadership/management experience

  • Demonstrated experience leading multiple cross-discipline teams

  • Extensive knowledge and experience with driving and applying design processes and research methodologies while working collaboratively with engineering, product management, and a variety of stakeholders

  • Mastery in 2-3 areas of expertise such as Product Design, Service Design, User Research, Visual Design, Interaction Design

  • Cultural sensitivity, creativity, resourcefulness, low ego, and a high EQ

  • A drive towards inclusive leadership and collaboration

  • Proficient at distilling complexity and storytelling

  • A strong portfolio showcasing problem-solving at large scale and high design caliber

Bonus points

  • Experience with change management, new products or business strategies, overseeing a diverse portfolio of products/end users

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 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.

We encourage our members to care for their whole selves, and we encourage our employees to do the same with comprehensive medical benefits, generous paid-time off, paid parental leave, retirement plans, company social events, stocked kitchens, wellness programs, and volunteer opportunities.

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.

Pay Transparency Policy

Oscar ensures that you won't be discharged or discriminated against based on whether you've inquired about, discussed, or disclosed your pay. Read the full policy here.

Job tags: Engineering Product design Product management Research Service design User experience User research Visual design
Job region(s): North America
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