VP, Sales

<p>Hi, we're Oscar. We're hiring a Vice President of Sales to join our Sales team.</p> <p>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.</p> <p><strong>About the role:</strong></p> <p>The VP of Sales leads Oscar’s growth engine, with a primary focus on the ACA (Individual) and ICHRA markets. This role is responsible for architecting Oscar’s distribution strategy—leveraging digital channels, broker relationships, and innovative employer solutions—to capture market share in the evolving health insurance landscape. The VP will scale a high-performing sales organization and ensure Oscar remains the preferred choice for individuals and employers transitioning to defined-contribution models.</p> <p>You will report into the Senior Vice President, Chief Growth Officer.</p> <p><strong>Work Location: </strong>This position is based in our New York office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid</p> <p><strong>Pay Transparency: </strong>The base pay for this role is: $198,720 - $260,820 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.</p> <p><strong>Responsibilities:</strong></p> <ul> <li><strong>ICHRA ACA Strategy:</strong> Design and execute a multi-year growth strategy specifically tailored to the ACA Exchange and the emerging ICHRA market for employers.</li> <li><strong>Distribution Channel Optimization:</strong> Oversee and expand Oscar’s broker and agency distribution networks; identify and integrate with digital platforms and enrollment partners.</li> <li><strong>KPI Revenue Ownership:</strong> Accountable for top-line revenue, membership growth targets (Individual and Group), and Cost of Acquisition (CAC) metrics.</li> <li><strong>Market Analysis:</strong> Monitor legislative shifts (state and federal) impacting ACA subsidies and ICHRA regulations to pivot sales tactics in real-time.</li> <li><strong>Retention Lifecycle Management:</strong> Partner with Member Engagement teams to maximize retention and lifetime value (LTV) of the existing membership base.</li> <li><strong>Cross-Functional Collaboration:</strong> Act as the "voice of the market" for Product and Actuarial teams to ensure Oscar’s plan designs and pricing are competitive in high-priority MSAs (Metropolitan Statistical Areas).</li> <li><strong>Contracting Negotiations:</strong> Lead high-level negotiations with major brokerage firms, General Agencies (GAs), and technology platform partners.</li> <li><strong>Regulatory Compliance:</strong> Ensure all sales activities and marketing materials meet CMS and state-specific Department of Insurance (DOI) guidelines.</li> <li>Compliance with all applicable laws and regulations</li> <li>Other duties as assigned</li> </ul> <p><strong>Requirements:</strong></p> <ul> <li>15+ years of sales leadership experience, with a proven track record of driving revenue in a high-growth environment.</li> <li>10+ years in the health insurance market, with deep technical knowledge of ACA mechanics and ICHRA structures.</li> <li>7+ years of experience managing and scaling large, remote, or geographically dispersed sales teams.</li> </ul> <p><strong>Bonus points:</strong></p> <ul> <li>Experience in<strong> </strong>InsureTech or tech-enabled healthcare organizations.</li> <li>Existing relationships with top-tier national brokerages and benefits consultants.</li> <li>Deep understanding of the "Defined Contribution" shift in employer benefits.</li> </ul><div class="content-conclusion"><p><span style="font-weight: 400;">This is a ... (truncated, view full listing at source)