Specialist, Sales Enablement and Training

ABOUT THE ROLE Oscar, a pioneering health insurance company, is seeking a Specialist, Sales Enablement and Training to join its Marketing team. As a key member of the team, this specialist will be responsible for developing and delivering impactful training programs and sales enablement resources to support the marketing organization. WHAT YOU'LL DO As a Specialist, Sales Enablement and Training, you will be responsible for facilitating webinars, developing engaging training materials, contributing to sales collateral, and driving adoption of key platforms and tools. Your primary goal will be to bring enablement strategy to life, ensuring every training interaction is engaging, accurate, and aligned with business goals. Key responsibilities include: - Developing B2B materials, including sales collateral, flyers, walkthroughs, demos, and product videos - Supporting sales efforts through creation of tailored materials, demos, and leading trainings - Driving platform adoption by building targeted training and onboarding programs - Supporting creation of webinars and leading webinars for Lucie and Trove - Compiling, organizing, and maintaining carrier training resources for internal and external use - Assisting with all webinar logistics, including scheduling, platform setup, registration, live facilitation, and post-session follow-up - Driving participant engagement through interactive formats, including Q&A, polling, scenario-based learning, and live demonstrations - Tracking webinar performance metrics and sharing insights and recommendations - Collaborating with marketing to align training and enablement initiatives with broader brand and campaign strategies - Compliance with all applicable laws and regulations WHAT YOU'LL NEED To be successful in this role, you will need: - 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 - 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) WHY REMOTE This is a fully remote position, open to candidates who reside in Dallas, TX. While our approach to work may adapt over time, the role will initially be performed remotely. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. BENEFITS As a full-time employee, you will be 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 - Paid wellness time and reimbursements