Bilingual Sales Trainer & Enablement Associate

About the role

Oscar is seeking a Bilingual Sales Trainer & Enablement Associate to design, deliver, and continuously improve sales training programs that boost agent performance and drive platform adoption. Reporting to the Head of Lucie Marketing, you will create engaging learning experiences in both English and Spanish for internal teams, agency partners, and external stakeholders.

Key responsibilities

• Partner with Sales leadership to design and deliver tailored training content, demos, and strategic sessions that improve win rates and deal velocity.
• Develop and execute targeted onboarding and platform‑adoption programs for agents.
• Create, schedule, and facilitate webinars in English and Spanish, handling all logistics and post‑session follow‑up.
• Compile and maintain carrier training resources for internal and external use.
• Track webinar performance metrics and provide actionable insights.
• Collaborate with Marketing to align training initiatives with broader brand and campaign strategies.

Required profile

• 5+ years of experience in sales training, enablement, or related fields.
• Proven ability to translate complex insurance and technology concepts into practical training.
• Strong facilitation, coaching, and communication skills in both English and Spanish.
• Experience working cross‑functionally with Sales, Marketing, Product, and Operations teams.

Required skills

What we offer

• Base salary ranging from $82,717 to $108,566 per year.
• Employee benefits and participation in Oscar's unlimited vacation program.
• Annual performance bonuses.