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Sales Training Specialist

Oscar, Tempe, AZ

A better kind of health insurance company


Sales Training Specialist

What is the position?

Oscar’s inside sales teams are core to our expansion and growth efforts. We’re looking for an experienced sales enablement specialist who has a strong track record of developing training curricula and content, facilitating classroom training sessions, and providing coaching to salespeople.

The Sales Training Specialist utilizes industry knowledge and expertise to create content for a variety of sales programs at Oscar. This person will be responsible for the design and facilitation process of Sales content for multiple sales programs. The role requires multiple skill sets: instructional design, facilitation, presentation, collaboration, coaching, and leadership.

What will you do?

  • Work with various stakeholders to ensure accurate program content
  • Build and test content for the various Oscar programs
  • Facilitate sales content in a classroom setting using best practices
  • Audit and update content on a regular cadence
  • Coach trainees on performance during training
  • Support other training initiatives as needed

Who are you?

  • You have excellent organizational skills
  • You are driven by results and focused on metrics
  • You possess incredible written and verbal communication skills
  • You are a quick learner and passionate about helping others learn
  • You are comfortable with different methods of instructional design
  • You have experience facilitating content you’ve built
  • You are comfortable with learning technologies (LMS, eLearning and video production software, etc.)

What are the qualifications?

  • 5+ years of sales training experience required
  • 3+ years of instructional design experience required
  • Health insurance sales experience preferred
  • Bachelor’s Degree preferred

If you are qualified and interested in applying, please note that a questionnaire assessment will be administered after you have submitted your application. 

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

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 ([email protected]) to make the need for an accommodation known. 

Pay Transparency Policy: Oscar's Pay Transparency Policy ensures that you won't be discharged or discriminated against based on whether you've inquired about, discussed, or disclosed your pay. Read the full policy here.



About Oscar

Founded in 2012, Oscar is probably the last thing you would expect from a technology startup – a seemingly old-fashioned healthcare insurance provider. The company provides clients with the kind of clarity and simplicity we have come to expect from an e-commerce site. And, of course, they're hiring.


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Want to learn more about Oscar? Visit Oscar's website.