Associate, Lucie Training & Sales Enablement

Oscar Health•New York, NY

20h•$91,908 - $120,629•Hybrid

About The Position

Oscar is seeking a Bilingual Sales Trainer & Enablement Associate to join their Marketing team. Oscar is a technology-driven health insurance company focused on member service. This role is responsible for creating, delivering, and improving sales training and enablement programs to boost agent performance and platform adoption. The associate will be the primary bilingual trainer, developing and delivering content in English and Spanish for internal teams, agency partners, and external stakeholders. This position requires collaboration with Sales, Marketing, Product, and Operations to translate complex insurance and technology concepts into practical training. The ideal candidate is an experienced facilitator, coach, and communicator passionate about adult learning, sales excellence, and agent success. The role reports to the Head of Lucie Marketing.

Requirements

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.
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 with the ability to engage audiences of varying experience levels.
Experience creating sales enablement content including presentations, training guides, videos, and digital learning resources.
Ability to simplify complex insurance, healthcare, and technology concepts into actionable learning.
Experience using webinar platforms (Zoom, GoToWebinar, Teams, etc.) and Learning Management Systems (LMS).
Strong project management, organization, and stakeholder management skills.
Proficiency in Microsoft Office, Google Workspace, and presentation software.

Nice To Haves

Health insurance related experience including familiarity with ACA Marketplace Insurance and ancillary/supplemental insurance
Experience in fast-paced environments

Responsibilities

Partner with Sales leadership to design and deliver tailored content, advanced demos, and strategic training sessions that directly improve win rates and deal velocity.
Operationalize Sales Leadership strategies by designing and executing targeted training demos for agents, while channeling field insights back to executives to refine corporate objectives.
Support sales efforts through creation of tailored materials, demos, and leading trainings.
Drive platform adoption by building targeted training and onboarding programs.
Support creation of webinars and lead webinars for Lucie and Trove in both English and Spanish.
Compile, organize, and maintain carrier training resources for internal and external use.
Assist with all webinar logistics including scheduling, platform setup, registration, live facilitation, and post-session follow-up.
Drive participant engagement through interactive formats including Q&A, polling, scenario-based learning, and live demonstrations.
Track webinar performance metrics and share insights and recommendations.
Collaborate with marketing to align training and enablement initiatives with broader brand and campaign strategies.
Compliance with all applicable laws and regulations.
Other duties as assigned.