Associate, Lucie Training & Sales Enablement

name; New York (NY); Hybrid; USD 92,000 - 121,000; Full time

Benefits offered by this job

Unlimited vacation

Annual performance bonuses

Job summary

Oscar is hiring a Bilingual Sales Trainer & Enablement Associate to join our Marketing team in New York. The role designs and delivers training to improve agent performance and platform adoption, in English and Spanish.

You will partner with Sales, Marketing, Product, and Operations to translate insurance and technology concepts into practical training. A seasoned facilitator with passion for adult learning and sales excellence is ideal.

Qualifications

• 5+ years of experience in Sales Training, Sales Enablement, Learning & Development, or Sales Operations.
• Fluency in English and Spanish with excellent written, verbal, and presentation skills.
• Experience designing and delivering instructor-led and virtual training programs.
• Experience coaching sales professionals, agents, brokers, or partner organizations.
• Strong presentation and facilitation skills for audiences of varying levels.
• Experience creating sales enablement content including presentations, guides, videos, and digital resources.
• Ability to simplify complex insurance, healthcare, and technology concepts into actionable learning.
• Experience using webinar platforms (Zoom, GoToWebinar, Teams) and Learning Management Systems (LMS).
• Strong project management, organization, and stakeholder management skills.
• Proficiency in Microsoft Office and Google Workspace.

Responsibilities

• Partner with Sales leadership to design and deliver tailored content and demos that improve win rates and deal velocity.
• Design and execute targeted training demos for agents; translate field insights to executives.
• Create materials, demos, and lead trainings to support sales efforts.
• Drive platform adoption by building targeted training and onboarding programs.
• Lead webinars in English and Spanish for Lucie and Trove platforms.
• Maintain and organize carrier training resources for internal and external use.
• Manage webinar logistics: scheduling, platform setup, registration, facilitation, and follow-up.
• Promote participant engagement via Q&A, polls, scenarios, and live demos.
• Track webinar performance and share insights and recommendations.
• Collaborate with Marketing to align enablement with brand campaigns.

Skills

Bilingual English/Spanish

Sales training & enablement

Facilitation & coaching

Presenter / communication

Project management

Tools

LMS

Zoom

GoToWebinar

Teams

PowerPoint

Excel

Google Workspace

Job description

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 New York 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: $91,908.00 - $120,629.25 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

• eligible for employee benefits
• participation in Oscar's unlimited vacation program
• 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

Learn more about how you can safeguard yourself from recruitment fraud here.

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

Pay Transparency:

Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience.

Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

• medical, dental, and vision benefits
• 11 paid holidays
• paid sick time
• paid parental leave
• 401(k) plan participation
• life and disability insurance
• paid wellness time and reimbursements

Artificial Intelligence (AI):

Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.

Reasonable Accommodation:

Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team ([e-mail]) to make the need for an accommodation known.

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