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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 (English/Spanish) for internal teams, agency partners, and external stakeholders.
Key responsibilities include partnering with Sales leadership to design tailored training content and advanced demos that improve win rates and deal velocity; operationalizing sales leadership strategies through targeted training sessions while channeling field insights back to executives; creating and delivering webinars in both English and Spanish; building targeted training and onboarding programs to drive platform adoption; compiling and maintaining carrier training resources; managing webinar logistics including scheduling, platform setup, registration, facilitation, and follow-up; driving participant engagement through interactive formats such as Q&A, polling, scenario-based learning, and live demonstrations; tracking webinar performance metrics; 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. Professional fluency in English and Spanish with exceptional written, verbal, and presentation skills in both languages is required. Demonstrated experience designing and delivering instructor-led and virtual training programs, coaching sales professionals and partner organizations, and creating sales enablement content (presentations, guides, videos, digital resources) is essential. Strong presentation and facilitation skills, ability to simplify complex insurance and technology concepts, experience with webinar platforms and learning management systems, proficiency in Microsoft Office and Google Workspace, and strong project management and stakeholder management skills are required. Health insurance experience and familiarity with ACA Marketplace Insurance are bonuses.
