Associate, Sales Enablement

Role Overview

Join Oscar’s Product Marketing Team as an Associate, Sales Enablement. This role drives the development, scaling, and execution of sales enablement strategy and marketing collateral across key distribution channels. You will serve as a bridge between growth strategy and field execution, ensuring external partners and internal teams have the necessary resources and expertise 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, and optimize the resource repository.

Why It Might Be a Fit

This role requires demonstrated success building clear sales assets, training decks, and playbooks, as well as experience navigating CRM platforms and digital enrollment tools. Excellent cross-functional communication skills are necessary, with a history of collaborating with Product Marketing, Legal, and Sales operations.

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
• Proven track record navigating CRM platforms and digital enrollment tools
• Excellent cross-functional communication skills

Benefits

• Employee benefits
• Unlimited vacation program
• Annual performance bonuses
• 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