Specialist, Sales Enablement and Training

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 position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid Pay Transparency: The base pay for this role is: $34.63 - $45.46 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 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) 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