Specialist, Sales Enablement and Training

Oscar Health is a health insurance company focused on serving its members through a technology platform. They are looking for a Specialist in Sales Enablement and Training to support the marketing organization by executing training programs and sales enablement resources, facilitating webinars, and developing training materials.

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

Skills

• 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
• Ability to 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)
• Health insurance related experience including familiarity with ACA Marketplace Insurance and ancillary/supplemental insurance

Benefits

• Employee benefits
• Monthly vacation accrual at a rate of 15 days per year
• 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

Company Overview