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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.
Key responsibilities include partnering with Sales leadership to design tailored content and strategic training sessions that improve win rates and deal velocity; operationalizing Sales Leadership strategies through targeted training demos for agents while channeling field insights back to executives; creating tailored materials and leading trainings to support sales efforts; driving platform adoption through targeted training and onboarding programs; and supporting creation and facilitation of webinars for Lucie and Trove in both English and Spanish.
Additional duties include compiling and maintaining carrier training resources, managing webinar logistics (scheduling, platform setup, registration, facilitation, follow-up), driving participant engagement through interactive formats (Q&A, polling, scenario-based learning, live demonstrations), tracking webinar performance metrics, and collaborating with marketing to align training initiatives with broader brand strategies.
The ideal candidate has 5+ years of experience in Sales Training, Sales Enablement, Learning & Development, or Sales Operations. Required qualifications include 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; experience coaching sales professionals, agents, brokers, or partner organizations; strong presentation and facilitation skills; experience creating sales enablement content (presentations, training guides, videos, digital learning resources); ability to simplify complex insurance, healthcare, and technology concepts; experience with webinar platforms and Learning Management Systems; strong project management and stakeholder management skills; and proficiency in Microsoft Office, Google Workspace, and presentation software.
Bonus qualifications include health insurance experience (ACA Marketplace, ancillary/supplemental insurance) and experience in fast-paced environments. The position is based in Tempe, Arizona, requiring a hybrid work schedule with 3 days in-office per week, with Thursdays as a required in-office day.
