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Salary: USD 91,908 - 120,629 / annual
Oscar Health is seeking a Bilingual Sales Trainer & Enablement Associate to join the Marketing team, reporting to the Head of Lucie Marketing. This role is central to designing, delivering, and continuously improving sales training and enablement programs that drive agent performance and platform adoption.
You will serve as the primary bilingual trainer (English/Spanish) for the organization, developing engaging learning experiences for internal teams, agency partners, and external stakeholders. Working closely with Sales, Marketing, Product, and Operations, you'll translate complex insurance and technology concepts into practical, results-driven training that empowers agents to succeed.
Key responsibilities include:
- Partner with Sales leadership to design tailored content, advanced demos, and strategic training sessions that improve win rates and deal velocity
- Operationalize Sales Leadership strategies by designing targeted training demos and channeling field insights back to executives
- Create tailored materials, demos, and lead training sessions to support sales efforts
- Drive platform adoption through targeted training and onboarding programs
- Design and lead webinars for Lucie and Trove in both English and Spanish
- Compile, organize, and maintain carrier training resources for internal and external use
- Manage webinar logistics including scheduling, platform setup, registration, facilitation, and follow-up
- Drive engagement through interactive formats (Q&A, polling, scenario-based learning, live demos)
- Track webinar performance metrics and share insights
- Collaborate with marketing to align training initiatives with brand and campaign strategies
Required qualifications:
- 5+ years 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
- 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 for audiences of varying experience levels
- Experience creating sales enablement content (presentations, guides, videos, digital resources)
- Ability to simplify complex insurance, healthcare, and technology concepts
- Experience with webinar platforms (Zoom, GoToWebinar, Teams) and Learning Management Systems
- Strong project management, organization, and stakeholder management skills
- Proficiency in Microsoft Office, Google Workspace, and presentation software
Bonus: Health insurance experience, ACA Marketplace familiarity, or experience in fast-paced environments.
The role is hybrid, based in the New York office, requiring 3 days in-office per week with Thursdays mandatory for team meetings and events.
