[Hiring] Specialist, Sales Enablement and Training @Oscar Health

Role Description

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
• Driving adoption of key platforms and tools
• Bringing 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 is a remote position, open to candidates who reside in Dallas, TX. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $31.17 - $40.91 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
• 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.

Benefits

• 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