Specialist, Sales Enablement and Training

About Oscar

Oscar is a health insurance company built on a full-stack technology platform with a strong focus on member service. Founded with the goal of creating a health insurance company that embodies the care and guidance of a "doctor in the family," Oscar aims to revolutionize the healthcare experience.

About the Role

The Specialist, Sales Enablement and Training 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. As a frontline facilitator, you will bring 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. While fully remote, future work models may adapt to include hybrid presence at a local hub office.

Responsibilities

• Assist in developing B2B materials, including sales collateral, flyers, walkthroughs, demos, and product videos.
• Support sales efforts through the creation of tailored materials, demos, and leading trainings.
• Drive platform adoption by building targeted training and onboarding programs.
• Support the 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 like 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.
• Ensure compliance with all applicable laws and regulations.
• Perform 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 diverse 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.

Pay Transparency

• Base Pay: $31.17 - $40.91 per hour.
• Eligibility: Eligible for employee benefits and monthly vacation accrual at a rate of 15 days per year.
• Final Offer: Base pay is determined by factors including relevant skills, education, and experience. Full-time employees are eligible for medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.