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 is a remote position, open to candidates who reside in: Dallas, TX. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area.

Pay Transparency

The base pay for this role is: $91,659 - $120,303 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%

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At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

Pay Transparency

Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience.

Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

Artificial Intelligence (ai)

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Reasonable Accommodation

Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team (accommodations@hioscar.com) to make the need for an accommodation known.

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