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Director, Sales

Hi, we're Oscar. We're hiring a Director, Sales to join our Sales team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

 

About the role:

The Director, Sales will lead the company’s sales efforts in our Florida and Texas markets. The role is responsible for growing membership in Oscar’s insurance products through the implementation of traditional insurance sales channels, as well as the pursuit of innovative sales strategies. On the traditional side, the Director, Sales 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, testing and iterating on ideas to drive engagement and influence desired behaviors of insured members will be important. 

You will report into the Vice President, Sales.

Work Location: This is a remote position based in the field, open to candidates who reside in Florida. Your daily work will involve a blend of work from your home office and frequent travel for client meetings. Occasional travel may be required for team meetings and company events. #LI-Remote

Pay Transparency: The base pay for this role is: $144,000 - $189,000 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and sales commissions.

 

Responsibilities:

  • Manage and develop the Sales team to support growth nationally.
  • Advocate on behalf of brokers, partners, and consumers within the business, and make business recommendations to internal partners that align with corporate goals.
  • Identify long term distribution partners based on ability to grow and drive desired outcomes.
  • Meet or exceed growth goals while providing great service to distribution partners. 
  • Synthesize and represent market performance to executive stakeholders.
  • Support employee development and influence corporate strategy.
  • Represent Oscar in the market at local broker and community events.
  • Act as the main point of contact and internal expert on workflow processes, escalation pathways, cross-functional points contacts for your direct reports.
  • Remain abreast of local competitive intelligence and market research.
  • Support team efforts to evaluate geographic expansion, new product lines, insurance plans and pricing.
  • Support Network Construction and Operations as needed.
  • Compliance with all applicable laws and regulations.
  • Other duties as assigned.

Requirements:

  • 10+ years of experience in the healthcare industry in an outside sales role where you were presenting and communicating with stakeholders at all levels.
  • 7+ years of experience building and maintaining relationships with business partners, internal and external. 
  • 5+ years of experience managing teams and leading cross functional initiatives.
  • 3+ years of experience in Salesforce.

Required Travel:

  • Up to 25%

 

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

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.

Pay Transparency:  Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

Artificial Intelligence (AI): Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.

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

California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Privacy Policy.

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CEO of Oscar Health
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Mark Bertolini
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Average salary estimate

$166500 / YEARLY (est.)
min
max
$144000K
$189000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

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Oscar Health is an American health insurance company headquartered in New York City. Through telemedicine, healthcare-focused technology interfaces, and clear claims pricing systems, the company focuses on the health insurance market.

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Full-time, remote
DATE POSTED
January 11, 2026
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