Note: The job is a remote job and is open to candidates in USA. Oscar is a health insurance company built around a full stack technology platform and a focus on serving its members. The Bilingual Sales Trainer & Enablement Associate designs, delivers, and improves sales training and enablement programs in English and Spanish to improve agent performance and platform adoption. The role partners with Sales, Marketing, Product, and Operations to create practical training, webinars, demos, and learning resources.
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
- 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
Skills
- 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
- This is a remote position, open to candidates who reside in: Dallas, Texas
- Health insurance related experience including familiarity with ACA Marketplace Insurance and ancillary/supplemental insurance
- Experience in fast-paced environments
Benefits
- Fully remote position for candidates who reside in Dallas, Texas
- Employee benefits
- Participation in Oscar's unlimited vacation program
- Annual performance bonuses
- Medical benefits
- Dental benefits
- Vision benefits
- 11 paid holidays
- Paid sick time
- Paid parental leave
- 401(k) plan participation
- Life insurance
- Disability insurance
- Paid wellness time and reimbursements
Company Overview