Ohio Sales Lead

Oscar, Cleveland, OH

A better kind of health insurance company

As a key member of Oscar’s sales team, you will lead the company’s go-to-market strategy for field sales in Cleveland. You’ll be responsible for growing membership in Oscar’s individual health insurance products through the management of traditional insurance sales channels, as well as the pursuit of innovative sales strategies. On the traditional side, you will drive Oscar’s broker strategy, ensuring that insurance brokers across our coverage area have the information and tools to effectively sell Oscar. On the creative side, you’ll test and iterate on ideas to drive buzz at a local level and create partnerships with local organizations to drive enrollment.

Winning factors: What leads to success

This is a unique opportunity to have a significant impact on the trajectory of a rapidly growing startup in a massive and important market. We’re looking for someone who is entrepreneurial, creative, and has a proven ability to drive revenue growth. We need someone with the ingenuity to develop new and innovative ways to reach prospective members and employers, as well as the discipline to measure the results and isolate the strategies that work. The ability to build tools, processes, and relationships from scratch, not just operate in an existing system, is key. Experience in the health insurance market is a plus, but our priority is finding a candidate with the right skills and attitude, to ensure Oscar’s continued growth in the Cleveland market.


  • Bachelor’s degree required. Advanced degree a plus.
  • Management and operations experience.
    • You have 5-7 years of experience managing teams and projects in complex, operational environments.
  • Sales experience.
    • You have a proven ability to drive revenue growth, and have preferably worked in a sales management capacity.
  • Strategic and analytical mindset. You take a structured approach to evaluating potential opportunities and develop well thought out strategies.
  • Executor. You don’t just operate at a high level. You do the hard work required to get things done and build processes that will scale.
  • Communicator. You have the ability to effectively communicate complex ideas, verbally and in writing.







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.

About Oscar

Founded in 2012, Oscar is probably the last thing you would expect from a technology startup – a seemingly old-fashioned healthcare insurance provider. The company provides clients with the kind of clarity and simplicity we have come to expect from an e-commerce site. And, of course, they're hiring.

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