Director, Sales

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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.

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 traditional insurance sales channels and 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 to the Vice President, Sales.

This is a remote position based in the field, open to candidates who reside in Florida. 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.

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.

• 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 of contact for 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.

• 10+ years of experience in the healthcare industry in an outside sales role with stakeholder-facing responsibilities.
• 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.

• Up to 25%

This is an authentic Oscar Health job opportunity. Oscar is an Equal Opportunity Employer. We cultivate an environment where people can be their most authentic selves and find belonging and support. If you require reasonable accommodations during the application process, contact the Oscar Benefits Team at

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