Bilingual Sales Trainer & Enablement Associate

Oscar Health Insurance; New York (NY); On-site; USD 83,000 - 109,000; Full time

Benefits offered by this job

Unlimited vacation

Annual performance bonuses

Job summary

Oscar Health Insurance is seeking a Bilingual Sales Trainer & Enablement Associate to design, deliver, and continuously improve sales training for agents and partners. You will create engaging English and Spanish learning experiences, partner with Sales, Marketing, Product, and Operations to translate complex insurance and tech concepts into practical programs, and drive platform adoption.

The role reports to the Head of Lucie Marketing.

Qualifications

• 5+ years of experience in Sales Training, Sales Enablement, Learning & Development, or Sales Operations.
• Professional fluency in English and Spanish with strong written, verbal, and presentation skills.
• 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 varied audiences.
• Experience creating sales enablement content (presentations, guides, videos, digital learning).
• Ability to simplify insurance, healthcare, and technology concepts into actionable learning.
• Experience using webinar platforms and LMS.

Responsibilities

• Design and deliver tailored content and demos to improve win rates and deal velocity.
• Operationalize Sales Leadership strategies through targeted training demos for agents.
• Create materials, demos, and lead trainings to support sales efforts.
• Drive platform adoption by building training and onboarding programs.
• Lead webinars in English and Spanish for Lucie and Trove.
• Maintain training resources for internal and external use.
• Manage webinar logistics including scheduling, setup, registration, facilitation, and follow-up.
• Track webinar performance and share insights to drive improvements.
• Collaborate with Marketing to align training with brand and campaigns.
• Ensure compliance with applicable laws and regulations.

Skills

Bilingual English/Spanish

Sales training

Facilitation

Presentation skills

Coaching

Tools

Zoom

GoToWebinar

Teams

LMS

Job description

Oscar Health Insurance is seeking a Bilingual Sales Trainer & Enablement Associate to design, deliver, and continuously improve sales training for agents and partners. You will create engaging English and Spanish learning experiences, partner with Sales, Marketing, Product, and Operations to translate complex insurance and tech concepts into practical programs, and drive platform adoption.

The role reports to the Head of Lucie Marketing.