Director, Engagement Marketing

Hi, we're Oscar. We’re hiring a Director of Engagement Marketing to join our Marketing team in our New York City 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.

About this role:

As the Director of Engagement Marketing, you will lead our Member Engagement team as we move into an exciting period of member growth. This team drives engagement amongst our members across 15 states and 29 markets throughout the year - from onboarding to renewals and everything in between. We are proud of our industry-leading 85% member retention rate, and hope to continuously improve upon it year-over-year. . 

You will shape the long-term strategy, processes, and infrastructure to provide an excellent year-round engagement program. You will partner with product managers, engineers, designers, data scientists, service teams, sales, and health care experts to understand and improve the experience for our members. 

You will report to the Chief Marketing Officer.


  • Manage a team of 9 and determine team strategy, priorities, and goals.
  • Oversee and help to build out the CRM function for the company.
  • Manage external relationships with key partners.
  • Manage the budget relating to our member-outreach efforts.
  • Lead strategy around how, when and why we communicate with our members.
  • Translate goals into delivery and infrastructure requirements, including: specifying required data, segmentation and targeting logic, and dynamic content requirements.
  • Be an expert on best practices, engagement strategies, and forward-looking opportunities that provide useful information and content when and how our members want to be communicated with.
  • Partner with Data and Product to build models to improve personalized communications and actions.
  • Improve product adoption and engagement metrics, and measure the success of these programs along the way.


  • 10+ years of experience in a marketing role, with experience in member engagement, retention, and lifecycle.
  • Experience managing a team, from setting the North Star to managing the team's daily work.
  • Experience growing and building a brand and consumer strategy.
  • Experience building new CRM strategies for a business with compelling results.
  • Experience driving engagement among multiple audience segments.


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 your unique background and perspectives.

We aim to make health care affordable and accessible for all, and apply this same vision to our perks and benefits, including: medical benefits, unlimited 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 ( 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.

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