Associate, Sales Enablement

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.

Direct experience supporting individual ACA sales models, with a solid understanding of how brokers build and scale their books of business.

Familiarity with agile product launches or tech-forward healthcare ecosystems, showing an ability to quickly translate rolling product updates into simple broker messaging.

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.

You will report into the Associate Director, Product Marketing.

Develop Multi-Audience Collateral: Design and deliver a high volume of targeted enablement resources that clearly translate Oscar's distinct market advantages

Build B2B2C and Localized Toolkits: Create state-specific market materials and comprehensive downstream enrollment guides that effectively advocate for Oscar

Architect Internal Training Programs: Design, build, and facilitate a comprehensive curriculum to establish deep subject matter expertise across our growth teams and the broader organization.