VP, Operations Sales

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.

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.

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

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.

• 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

• 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…