Associate, Sales Enablement

Role Overview

This role drives the development, scaling, and execution of our sales enablement strategy and marketing collateral across our key distribution channels. You will serve as the critical bridge between our growth strategy and field execution, ensuring external partners and internal teams have the high-impact resources and deep subject matter expertise needed to confidently evangelize Oscar and accelerate membership acquisition.

What You Will Do

Develop Multi-Audience Collateral, Build B2B2C and Localized Toolkits, Architect Internal Training Programs, Support Strategic Event Execution, Optimize the Resource Repository.

Why It Might Be a Fit

Demonstrated success building clear, scannable sales assets, training decks, and playbooks that simplify complex insurance products for broker audiences. Proven track record navigating CRM platforms and digital enrollment tools to track broker engagement metrics and pull actionable sales insights.

Requirements

• Bachelors degree or 4+ years commensurate experience
• 1–3 years of experience in sales enablement, broker relations, account management, or corporate training
• Demonstrated success building clear, scannable sales assets, training decks, and playbooks that simplify complex insurance products for broker audiences.
• Proven track record navigating CRM platforms (like Salesforce) and digital enrollment tools to track broker engagement metrics and pull actionable sales insights.
• Excellent cross-functional communication skills, with a history of collaborating directly with Product Marketing, Legal, and Sales operations to manage tight compliance and rollout deadlines.

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
• unlimited vacation program
• annual performance bonuses