Sales Executive

About the Role

The Sales Executive is entrusted with the critical mission of driving membership expansion through the cultivation of strategic partnerships with brokers and agencies in the Miami region. This position requires the hire to identify and qualify distribution partners, ensuring that insurance professionals across Miami and surrounding regions are fully equipped with the tools necessary to effectively sell Oscar's product suite. The Sales Executive owns the full cycle of the sales process, reporting directly to the Director, Sales, and acting as the primary point of contact for ensuring market penetration. This role involves conducting in-depth research to uncover high-value accounts and hidden broker opportunities within targeted segments, focusing on building trusted relationships. The hire will guide qualified leads toward selecting Oscar by clearly articulating coverage options and the distinct value delivered to members, navigating complex decisions with clarity. Success in this position is defined by the ability to represent Oscar at industry events and conferences, maintaining a strong market presence evenings and weekends when necessary to meet business objectives.

Key Facts

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Location: USA

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Engagement: Full-time employment with eligibility for Oscar benefits and participation in the unlimited vacation program, plus sales commissions.

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Compensation: Base salary range is $75,348.00 to $98,894.25 per year.

What you'll do

• Execute a targeted outreach strategy to identify and engage high-potential insurance brokers and agencies within the Miami market.
• Build and maintain trusted, consultative relationships with distribution partners through tailored conversations that highlight product strengths.
• Conduct in-depth research to uncover new broker opportunities and map key decision-makers within target accounts.
• Fluently communicate product details and coverage options in both English and Spanish to ensure partners can effectively sell to diverse members.
• Represent Oscar at industry events, conferences, and partner meetings, managing scheduling that may include evenings and weekends.
• Maintain meticulous records within the CRM system to ensure every interaction, promise, and follow-up is visible and actionable for the team.
• Collaborate with marketing teams to shape outreach strategies and design campaigns that resonate deeply with brokers and agencies.
• Champion improvements to sales tools and workflows, testing new methodologies that make the selling process easier and more consistent.
• Adhere strictly to all insurance regulations and compliance standards in every interaction and documentation step.
• Translate complex insurance concepts into clear, compelling narratives that address client pain points and drive decision-making.
• Proactively share market feedback and insights from broker conversations to influence product and operational improvements.
• Manage a full pipeline of leads, prioritizing opportunities based on potential impact and likelihood of conversion.
• Partner with internal stakeholders to resolve partner inquiries and ensure a seamless experience for brokers and agencies.
• Drive the achievement of sales quotas and distribution goals through disciplined execution and strategic planning.
• Act as an Oscar ambassador, embodying the company's values in every interaction with partners and members.

Requirements

Candidates must possess three or more years of healthcare sales experience, demonstrating a track record of growth and results in a demanding environment. They must communicate confidently with leaders at any level, presenting ideas and negotiating terms effectively in person and remotely. A valid insurance license or the ability to obtain one within the first 90 days is required to ensure compliance and credibility in the market. Fluency in both English and Spanish is mandatory to serve diverse members and partners without friction or misinterpretation. The ability to manage multiple priorities and deadlines in a fast-paced environment is essential for success in this role. Candidates must be comfortable working remotely while maintaining a strong presence during required travel and company events. Adherence to company policies and ethical standards is non-negotiable in every aspect of the position. The role requires a high level of self-motivation and discipline to manage a distributed workload without direct supervision.

Nice to have

A bachelor's degree or four years of relevant experience that demonstrates strategic thinking and market awareness is valued. Proficiency in Salesforce to generate insights and accurately track progress is also considered an asset for optimizing pipeline management.

Practical Notes

This role operates on a remote-first basis with required travel to client locations and company events. Please note that the schedule may include evenings and weekends to maintain a strong market presence and meet event commitments. The position is based in Miami, Florida, but the primary work arrangement is remote.