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Salary: USD 82,717 - 108,566 / annual
Oscar Health is seeking a Bilingual Sales Trainer & Enablement Associate to design, deliver, and continuously improve sales training and enablement programs that drive agent performance and platform adoption. This role serves as the primary bilingual trainer for the organization, developing and delivering engaging learning experiences in both English and Spanish for internal teams, agency partners, and external stakeholders.
You will partner closely with Sales, Marketing, Product, and Operations to translate complex insurance and technology concepts into practical, results-driven training. Key responsibilities include designing and delivering tailored content and advanced demos that improve win rates and deal velocity; operationalizing sales leadership strategies through targeted training for agents; creating tailored materials and leading trainings to support sales efforts; driving platform adoption through targeted training and onboarding programs; supporting creation and leading of webinars for Lucie and Trove in both English and Spanish; compiling and maintaining carrier training resources; assisting with webinar logistics including scheduling, platform setup, registration, facilitation, and follow-up; driving participant engagement through interactive formats including Q&A, polling, scenario-based learning, and live demonstrations; tracking webinar performance metrics and sharing insights; and collaborating with marketing to align training initiatives with broader brand and campaign strategies.
The ideal candidate has 5+ years of experience in sales training, sales enablement, learning & development, or sales operations. You must have professional fluency in English and Spanish with exceptional written, verbal, and presentation skills in both languages. Demonstrated experience designing and delivering instructor-led and virtual training programs is essential, as is experience coaching sales professionals, agents, brokers, or partner organizations. Strong presentation and facilitation skills with the ability to engage audiences of varying experience levels are required. You should have experience creating sales enablement content including presentations, training guides, videos, and digital learning resources, and the ability to simplify complex insurance, healthcare, and technology concepts into actionable learning. Experience using webinar platforms (Zoom, GoToWebinar, Teams, etc.) and Learning Management Systems (LMS) is necessary. Strong project management, organization, and stakeholder management skills are critical, along with proficiency in Microsoft Office, Google Workspace, and presentation software. Health insurance experience, including familiarity with ACA Marketplace Insurance and ancillary/supplemental insurance, is a bonus, as is experience in fast-paced environments.
