Hi, we're Oscar. We're hiring a Vice President, Sales 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.
Pay Transparency: The base pay for this role is: $240,120 - $315,157.50 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 operational realities of regulated growth.
- Experience managing large-scale system conversions at national companies and/or business operating models
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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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