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 is a remote position, open to candidates who reside in: Dallas, Texas. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote
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
This is an authentic Oscar Health job opportunity. 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.
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 ([email protected]) to make the need for an accommodation known.
California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Privacy Policy.
Skills Required
- 5+ years of experience in Sales Training, Sales Enablement, Learning & Development, or Sales Operations
- Professional fluency in English and Spanish, including exceptional written, verbal, and presentation skills in both languages
- 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 such as Zoom, GoToWebinar, or Teams and Learning Management Systems
- Strong project management, organization, and stakeholder management skills
- Proficiency in Microsoft Office, Google Workspace, and presentation software
- Health insurance experience, including familiarity with ACA Marketplace Insurance and ancillary or supplemental insurance
- Experience working in fast-paced environments
Oscar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Oscar Health and has not been reviewed or approved by Oscar Health.
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Healthcare Strength — Employer-sponsored medical coverage for employees and their families with mental-health support is prominently offered. Wellness programming and digital care access add to perceived strength.
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Parental & Family Support — Paid parental leave of 10+ weeks, backup care, and family-forming support (including fertility and adoption benefits) are part of the package. Reproductive‑loss leave is also noted.
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Leave & Time Off Breadth — Multiple time‑off options, wellness days, and an unlimited vacation program for some roles are described. Paid holidays, paid sick time, and a long‑tenure sabbatical broaden time‑away choices.
Oscar Health Insights
What We Do
Health care is broken; we're trying to fix it. The Oscar team is focused on utilizing technology, design and data to humanize health care. We're a group of technology and health care professionals who looked at the current state of the US health care system, got frustrated by the horrible consumer experience, and decided to do something big about it. Backed by a renowned set of investors and advisors, we’ve set out to revolutionize health care.
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