Associate, Sales Enablement

Hi, we're Oscar. We're hiring an Associate, Sales Enablement to join our Product Marketing Team.

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.

About the role:

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.

Work Location: This position is based in our New York office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $101,844 - $133,670 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• 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.
• Support Strategic Event Execution: Partner closely with the Growth and Marketing teams to manage asset readiness and collateral delivery for high-stakes industry events, regional rollouts, and the critical Open Enrollment calendar.
• Optimize the Resource Repository: Gather continuous feedback from sales loops and distribution partners to proactively iterate, update, and maintain a centralized, high-impact library of market-facing resources.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelors degree or 4+ years commensurate experience
• 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.

Bonus points:

• Bachelor's degree in Marketing, Business Administration, Communications, Healthcare Management, or a related field.
• Direct experience supporting individual ACA sales models, with a solid understanding of how brokers build and scale their books of business.
• Advanced proficiency with design and enablement software (such as Figma, Canva, or Highspot) to independently build modern, high-end visual assets.
• Familiarity with agile product launches or tech-forward healthcare ecosystems, showing an ability to quickly translate rolling product updates into simple broker messaging.

Travel required - Up to 10%