Sales Enablement and Training Specialist

Responsibilities

• Assist in developing B2B materials, including sales collateral, flyers, walkthroughs, demos, and product videos
• Support sales efforts through the creation of tailored materials and leading training sessions
• Drive platform adoption by building targeted training and onboarding programs
• Support the creation of and lead webinars, managing all logistics from scheduling to post-session follow-up
• Compile, organize, and maintain carrier training resources for internal and external use
• Drive participant engagement through interactive formats like Q&A, polling, and scenario-based learning
• Track webinar performance metrics and share insights and recommendations
• Collaborate with marketing to align enablement initiatives with broader brand and campaign strategies

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 and professional presentations
• Strong ability to simplify complex insurance and technology concepts for various audiences
• Bachelor's degree in Business, Marketing, Communications, Education, or a related field

Preferred Qualifications

• Health insurance related experience, including familiarity with ACA Marketplace Insurance and ancillary/supplemental insurance

About the Company

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.