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Oscar Health // health insurance
Tempe, Arizona, United States    Posted: Tuesday, August 03, 2021
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Hi, we're Oscar. Were hiring a Training Expert to join our Broker Support team in our Tempe  office. 

Oscar is a technology-driven, consumer-focused health insurance startup founded in 2012 & headquartered in New York City. Our goal is to make health insurance simple, transparent, & human. We need your help to do so.

About the role:

As a Training Expert youll be responsible for managing & executing the onboarding & refresher training for frontline representatives in a particular business area. In this role, youll ensure a robust onboarding experience, as well as a smooth transition for new hires from training to production. You will successfully onboard new hires & work closely with department leads to identify training gaps & deliver refresher training to address those gaps. 

You will report to the Associate Operations Manager.


  • Schedule training sessions for new hires, & ensure all trainings are prompt, efficient, & run smoothly
  • Manage all new hire communications & troubleshooting any issues related to onboarding; track where all new hires are in the funnel on an ongoing basis
  • Collaborate with Learning Specialists & Program Managers on program content
  • Identify gaps in department knowledge in order to create, iterate, & launch trainings
  • Work cross functionally to support new hire onboarding - from system access to orientation & team introductions
  • Facilitate onboarding/refreshers courses to Oscar employees within a particular business unit
  • Manage the transition from training to production & facilitate sign off process 
  • Complete assessments with new hires & provide feedback (to them & to managers)
  • Create a training library for teams to reference & ensure materials are updated to align with company changes
  • Create & Update Confluence (our knowledge base) for the business area to ensure it supports onboarding objectives
  • Hold post-onboarding roundtables to gather & act on feedback
  • Participate in train-the-trainer sessions


  • 3+ years of customer support/service experience or Bachelors Degree Required
  • 1+ years of experience in presenting to groups, training, & coaching others
  • 1+ years of experience in building, iterating, & revamping training content  
  • Advanced computer literacy skills with experience multitasking between required tools
  • Experience using data to make decisions & ability to problem solve 

Bonus points:

  • Healthcare experience
  • Learning & development experience

Life at Oscar: 

Our more than 1,000 employees aim to make health care affordable & accessible for all. We apply this same vision to our perks & benefits, including: medical benefits, generous paid-time off, paid parental leave, retirement plans, company social events, stocked kitchens, wellness programs, & volunteer opportunities.

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 & find both belonging & support. We're on a mission to change health care -- an experience made whole by your unique background & perspectives.

Reasonable Accommodation

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

Pay Transparency Policy

Oscar 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.

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