Specialist, Sales Enablement and Training

Oscar Health • New York, NY

7h • $35 - $45 • Hybrid

About The Position

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.

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
• 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)

Nice To Haves

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

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

Benefits

• medical
• dental
• vision benefits
• 11 paid holidays
• paid sick time
• paid parental leave
• 401(k) plan participation
• life and disability insurance
• paid wellness time and reimbursements
• monthly vacation accrual at a rate of 15 days per year

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level