Bilingual Sales Enablement Specialist

name; New York (NY); Hybrid; USD 92,000 - 121,000; Full time

Benefits offered by this job

Unlimited vacation

Annual performance bonuses

Job summary

Oscar is hiring a Bilingual Sales Trainer & Enablement Associate to join our Marketing team in New York. The role designs and delivers training to improve agent performance and platform adoption, in English and Spanish.

You will partner with Sales, Marketing, Product, and Operations to translate insurance and technology concepts into practical training. A seasoned facilitator with passion for adult learning and sales excellence is ideal.

Qualifications

• 5+ years of experience in Sales Training, Sales Enablement, Learning & Development, or Sales Operations.
• Fluency in English and Spanish with excellent 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 audiences of varying levels.
• Experience creating sales enablement content including presentations, guides, videos, and digital resources.
• Ability to simplify complex insurance, healthcare, and technology concepts into actionable learning.
• Experience using webinar platforms (Zoom, GoToWebinar, Teams) and Learning Management Systems (LMS).
• Strong project management, organization, and stakeholder management skills.
• Proficiency in Microsoft Office and Google Workspace.

Responsibilities

• Partner with Sales leadership to design and deliver tailored content and demos that improve win rates and deal velocity.
• Design and execute targeted training demos for agents; translate field insights to executives.
• Create materials, demos, and lead trainings to support sales efforts.
• Drive platform adoption by building targeted training and onboarding programs.
• Lead webinars in English and Spanish for Lucie and Trove platforms.
• Maintain and organize carrier training resources for internal and external use.
• Manage webinar logistics: scheduling, platform setup, registration, facilitation, and follow-up.
• Promote participant engagement via Q&A, polls, scenarios, and live demos.
• Track webinar performance and share insights and recommendations.
• Collaborate with Marketing to align enablement with brand campaigns.

Skills

Bilingual English/Spanish

Sales training & enablement

Facilitation & coaching

Presenter / communication

Project management

Tools

LMS

Zoom

GoToWebinar

Teams

PowerPoint

Excel

Google Workspace

Job description

Oscar is hiring a Bilingual Sales Trainer & Enablement Associate to join our Marketing team in New York. The role designs and delivers training to improve agent performance and platform adoption, in English and Spanish.

You will partner with Sales, Marketing, Product, and Operations to translate insurance and technology concepts into practical training. A seasoned facilitator with passion for adult learning and sales excellence is ideal.