O
Oscar Health
Lucie Training & Sales Enablement Associate
Skills
Sales OpsCompliance
2 months ago
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Important information
Salary:
$91,908 – $120,629 / year
Location:
New York, NY, USA
Work mode:
Onsite
Published on:
31 August 2026
What they need
Who you are
- The ideal candidate is an experienced facilitator, coach, and communicator who is passionate about adult learning, sales excellence, and empowering agents to succeed
- 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
- Health insurance related experience including familiarity with ACA Marketplace Insurance and ancillary/supplemental insurance
- Experience in fast-paced environments
What the job involves
- The Bilingual Sales Trainer & Enablement Associate is responsible for designing, delivering, and continuously improving sales training and enablement programs that drive agent performance, and platform adoption
- Serving as the primary bilingual trainer for the organization, this role develops and delivers engaging learning experiences in both English and Spanish for internal teams, agency partners, and external stakeholders
- This position partners closely with Sales, Marketing, Product, and Operations to translate complex insurance and technology concepts into practical, results-driven training
- You will report into the Head of Lucie Marketing
- Partner with Sales leadership to design and deliver tailored content, advanced demos, and strategic training sessions that directly improve win rates and deal velocity
- Operationalizes 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
- Work to 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
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