VP, Sales

Hi, we're Oscar. We're hiring a Vice President of 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 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.

You will report into the Senior Vice President, Chief Growth Officer.

Work Location

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.

Pay Transparency

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.

Responsibilities

Ichra & Aca Strategy

Design and execute a multi-year growth strategy specifically tailored to the ACA Exchange and the emerging ICHRA market for employers.

Distribution Channel Optimization

Oversee and expand Oscar’s broker and agency distribution networks; identify and integrate with digital platforms and enrollment partners.

Kpi & Revenue Ownership

Accountable for top-line revenue, membership growth targets (Individual and Group), and Cost of Acquisition (CAC) metrics.

Market Analysis

Monitor legislative shifts (state and federal) impacting ACA subsidies and ICHRA regulations to pivot sales tactics in real-time.

Retention & Lifecycle Management

Partner with Member Engagement teams to maximize retention and lifetime value (LTV) of the existing membership base.

Cross-functional Collaboration

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).

Contracting & Negotiations

Lead high-level negotiations with major brokerage firms, General Agencies (GAs), and technology platform partners.

Regulatory Compliance

Ensure all sales activities and marketing materials meet CMS and state-specific Department of Insurance (DOI) guidelines.

Compliance with all applicable laws and regulations

Other duties as assigned

Requirements

15+ years of sales leadership experience, with a proven track record of driving revenue in a high-growth environment.

10+ years in the health insurance market, with deep technical knowledge of ACA mechanics and ICHRA structures.

7+ years of experience managing and scaling large, remote, or geographically dispersed sales teams.

Bonus Points

Experience In

InsureTech or tech-enabled healthcare organizations.

Existing relationships with top-tier national brokerages and benefits consultants.

Deep understanding of the "Defined Contribution" shift in employer benefits.

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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 (accommodations@hioscar.com) to make the need for an accommodation known.

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