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Creative Director

| Greater NYC Area

The Creative Director will work closely with marketing, sales and broader business teams to build Oscar's brand narrative, creating an internal agency that spans design, editorial, video, digital, and more. You will also create a consistent end-to-end brand experience across multiple marketing touch-points. Working closely with marketing, engineering, design, data, member services, sales, and healthcare experts you will strive to understand, conceptualize, build, and engage a wide audience of industry professionals, members, and potential customers.

We're seeking an original thinker and expressive brand storyteller — someone who cares deeply about the work they do with a driving curiosity to push boundaries within an already dynamic and authentic brand.

Oscar needs someone who will...

  • Create engaging work on traditional and non-traditional channels focused on acquiring, engaging, and educating a diverse audience of healthcare professionals, businesses, consumers, and members on the value of Oscar.

  • Constantly evolve and push boundaries in developing Oscar’s brand and creative via content, channel, and experiences. Oscar is disrupting and innovating the healthcare industry, and our creative should, too.

  • Partner cross-functionally with key stakeholders to ensure creative work is addressing Oscar’s strategic goals. This means working closely with marketing, design, and product to bring concepts to final execution.

  • Understand, in a data driven environment, how to appeal to the heart as well as the mind.

In the first 90 days, you will...

  • Be excited to deep dive — become well-versed in the healthcare industry, and bring a friendly and consumer-oriented approach to translating the complexities of insurance to prospective members.

  • Build, mentor, and lead a multi-functional creative team of talented and passionate individuals across disciplines.

  • Immerse yourself in being an Oscar member in physical and digital spaces and consider opportunities for evolving the touchpoints.


  • Are a strong conceptual thinker and a builder at heart. You believe that a creative approach to any problem will yield a stronger result

  • Love working at a strategic level, but you’re happy to roll up your sleeves when needed

  • Aren’t limited by job titles — great work can come from anywhere

  • Are excited to join a company with real startup culture (and perhaps leave the Advertising world behind)

 You will...

  • Work closely with the design and marketing team to tell compelling stories through multiple channels (digital, TV, print, etc.)

  • Successfully guide the work from start to finish, partnering with outside vendors, internal designers, and the marketing team to provide valuable input

  • Play a leadership role in guiding strategic creative decisions and gain buy-in from stakeholders on proposed creative solutions

  • Be an internal and external advocate for the Oscar Brand (voice, tone, design, etc) 

What you bring...

  • A love of technology equal to art/copy.

  • A strong portfolio demonstrating a passion and ability to lead creative initiatives across a wide range of platforms (TV, web, print, OOH). You’ve led projects through full strategic and creative development — research, strategy (why and how), naming, copywriting, and content development.

  • The ability to inspire others and demonstrated experience of building and developing teams with clear goals and measurable impact.

  • The belief that effective creative direction to get to the best work is achieved through collaboration in small, fast-moving teams.

  • 10+ years experience working either in-house or at an agency.

Above all else you...

  • Are friendly, thoughtful, and kind

  • Always have an informed point of view and an open mind

  • Are inspired by Oscar’s mission and goals and excited to help fix a broken system

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

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 ([email protected]) to make the need for an accommodation known.

Pay Transparency Policy: Oscar's Pay Transparency Policy 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.

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295 Lafayette St, New York, NY 10012