VP, Operations

Position: VP, Growth Operations
Hi, we're Oscar. We're hiring a Vice President, Growth Operations 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:

This role is the operational backbone of our national growth strategy across ACA, ICHRA, and partner distribution. Reporting to the Chief Growth Office, this is a senior, highly visible leadership role responsible for translating growth strategy into scalable, compliant, and data-driven execution across brokers, agencies, platforms, and partners. This role will have end-to-end ownership of growth operations, including broker oversight, enrollment operations governance, CRM and tooling strategy, integrations, and executive reporting-partnering closely with Growth, Finance, Product, Legal, Compliance, and Data teams.

This role requires strong executive presence, sharp operational judgment, and the ability to move fluidly between leadership-level strategy discussions and hands-on engagement with complex data, workflows, and regulatory consideration.

You will report into the SVP, 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. #LI-Hybrid

Pay Transparency: The base pay for this role is: $240,120 - $ per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Own the strategic design, operational execution, and governance of national broker and agency compensation programs across ACA and ICHRA, ensuring accuracy, scalability, and regulatory compliance.
• Provide executive leadership over broker enrollment operations and regulatory adherence, partnering closely with Legal and Compliance to establish durable controls, monitoring, and risk mitigation frameworks.
• Advance Oscar's growth operations analytics by scaling a unified, enterprise-grade reporting framework that delivers timely, decision-ready insights across broker performance, enrollment, revenue, and compliance-supporting executive decision-making and long-range growth planning.
• Set the strategy for broker support, onboarding, training, and servicing across all channels, ensuring a consistent, high-quality experience for Oscar's distribution partners.
• Serve as the senior escalation point for complex broker, partner, and operational issues, coordinating across Growth, Legal, Compliance, Clinical, and Product teams to drive timely and effective resolution.
• Lead teams supporting key agencies and strategic partners while managing external BPO and servicing vendors, holding partners accountable to performance, quality, and compliance standards.
• Negotiate and oversee contracts with partner platforms and vendors; establishing service level agreements that ensure quality, affordability and turnaround times/access needs support Oscar's competitive position
• Own the operational and technical roadmap for growth-related integrations, including eligibility platforms, enrollment vendors, exchange interfaces, and downstream operational systems.
• Lead enterprise CRM strategy and execution (Salesforce), ensuring it enables sales productivity, accurate reporting, partner visibility, and effective campaign execution across ACA and ICHRA channels.
• Direct audits, performance management, and optimization of third-party growth technology vendors to ensure a seamless end-to-end experience for brokers, partners, and members.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree
• 15+ years of experience in growth, operations, revenue operations, or distribution leadership roles, with increasing scope and complexity
• 5+ years of experience managing a sales or sales operations teams
• 5+ years directly managing information systems, Salesforce, CRM, platform integrations and end-to-end system conversions.
• 5+ years of experience establishing performance management systems, including key metrics development and strategy development and tracking
• 5+ years of experience scaling growth or distribution operations in a regulated, mid-to-late-stage health tech or insurance environment

Bonus points:

• Strong command of Salesforce architecture and healthcare-specific data integrations; able to translate business needs into scalable system and reporting solutions
• System Integration SME
• Proven ability to foster strong internal relationships with partners
• Tech focused mind-set with the ability to set a vision around optimization
• Deep experience in health insurance or health tech, with a strong grasp of ACA, ICHRA, broker distribution, and the…