Hi, we're Oscar. We're hiring a Specialist, Sales Enablement and Training 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 Sales Enablement and Training Specialist supports the marketing organization by executing and delivering impactful training programs and sales enablement resources. This role is responsible for facilitating webinars, developing engaging training materials, contributing to sales collateral, and driving adoption of key platforms and tools. This individual serves as a frontline facilitator who brings enablement strategy to life, ensuring every training interaction is engaging, accurate, and aligned with business goals.
You will report into the Head of Lucie Marketing.
Work Location: This is a remote position, open to candidates who reside in: Dallas, TX. 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: $31.17 - $40.91 per hour. You are also eligible for employee benefits and monthly vacation accrual at a rate of 15 days per year.
Responsibilities:
- Assist in developing B2B materials, including sales collateral, flyers, walkthroughs, demos, and product videos
- 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
- 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:
- 1+ years of experience in training, sales enablement, learning & development, or a related role
- Experience developing training materials, sales collateral, and multimedia content (including demos and video)
- Familiarity with ACA Marketplace, CMS regulations, and Supplemental products
- Experience leading webinars, presentations, and creating training materials
- Support sales enablement initiatives
- Strong ability to simplify complex insurance and technology concepts for audiences
- Bachelor's degree in Business, Marketing, Communications, Education, or a related field (or equivalent professional experience)
Bonus points:
- Health insurance related experience including familiarity with ACA Marketplace Insurance and ancillary/supplemental insurance.
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
- 1+ years of experience in training, sales enablement, learning & development, or a related role
- Experience developing training materials, sales collateral, and multimedia content (including demos and video)
- Familiarity with ACA Marketplace, CMS regulations, and Supplemental products
- Experience leading webinars, presentations, and creating training materials
- Support sales enablement initiatives
- Strong ability to simplify complex insurance and technology concepts for audiences
- Bachelor's degree in Business, Marketing, Communications, Education, or a related field (or equivalent professional experience)
- Reside in Dallas, TX (role open to candidates who reside in Dallas metro)
- Health insurance related experience including familiarity with ACA Marketplace Insurance and ancillary/supplemental insurance
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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