Sales Enablement and Training Specialist

Responsibilities

• Assist in developing B2B materials, including sales collateral, flyers, walkthroughs, demos, and product videos
• Support sales efforts through the creation of tailored materials and leading training sessions
• Drive platform adoption by building targeted training and onboarding programs
• Support the creation of webinars and lead live sessions for Lucie and Trove
• Manage all webinar logistics, including scheduling, platform setup, registration, and post-session follow-up
• Drive participant engagement through interactive formats such as Q&A, polling, and scenario-based learning
• Track webinar performance metrics and share actionable insights and recommendations
• Collaborate with the marketing team to align enablement initiatives with broader brand and campaign strategies

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 and professional presentations
• Strong ability to simplify complex insurance and technology concepts for diverse audiences
• Bachelor's degree in Business, Marketing, Communications, Education, or a related field

Preferred Qualifications

• Health insurance industry experience
• Familiarity with ACA Marketplace Insurance and ancillary/supplemental insurance

Benefits

• Competitive hourly pay ($31.17 - $40.91 per hour)
• Medical, dental, and vision benefits
• 11 paid holidays and paid sick time
• Paid parental leave
• 401(k) plan participation
• Life and disability insurance
• Paid wellness time and reimbursements

About the Company

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.