Training Enablement Associate Jobs (NOW HIRING)

Hi, we're Oscar. We're hiring a Bilingual Sales Trainer & Enablement Associate to join our Marketing team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves-one that behaves like a doctor in the family.

About the role:

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. The ideal candidate is an experienced facilitator, coach, and communicator who is passionate about adult learning, sales excellence, and empowering agents to succeed.

You will report into the Head of Lucie Marketing.

Work Location: This position is based in our Tempe, Arizona office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $82,717.20 - $108,566.33 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

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

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.

Bonus points:

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