Senior Learning Specialist

oscar· Member Programs
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About this role

Hi, we're Oscar. We're hiring a Senior Learning Specialist to join our Decentralized Learning team.

Oscar is the first health insurance company built around a full stack technology platform and a 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

You will design and facilitate training content to foster a workforce. You will help achieve high-quality training standards in consideration of important business outcomes.

You will report to the Associate Operations Manager of Decentralized Learning.

Work Location: This position is based in our New York City 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: $75,348- $98,894 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, and annual performance bonuses.

Responsibilities

  • Create and develop both instructor-led and eLearning content by authoring and LMS tools, applying adult learning theory to maximize learner success
  • Facilitate instructor-led courses across multiple audiences, ensuring engagement from both in-person and remote learners
  • Collaborate with subject matter experts to source important content needed to design trainings
  • Audit and update training content, using subject matter experts and learning feedback to ensure accuracy and effectiveness
  • Identify opportunities to reduce waste in training content through consolation and standardization
  • Compliance with all applicable laws and regulations
  • Other duties as assigned

Qualifications

  • 2+ years experience developing training in a production environment, including eLearning design
  • 2+ years experience working with teams in multiple locations within multiple disciplines
  • 2+ years working in a collaborative environment with a diverse set of people

Bonus points

  • 2+ years experience facilitating or presenting in company meetings
  • PMP or Six Sigma Certified
  • Instructional Design Certification
  • Experience working in Health Insurance
  • Bachelor's degree
  • Experience facilitating or building training
  • Experience working in a call center support function
  • Experience working in a regulated industry

This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here

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): Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.

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.

California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Privacy Policy.

Frequently Asked Questions

Is the salary disclosed for the Senior Learning Specialist position at oscar?
The salary for this Senior Learning Specialist role at oscar is not publicly listed. Click "Apply Now" to learn more about the compensation package on their official careers page.
Where is the Senior Learning Specialist position at oscar located?
This Senior Learning Specialist role at oscar is based in New York, New York, United States. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Which team or department does the Senior Learning Specialist at oscar belong to?
This Senior Learning Specialist position is part of the Member Programs department at oscar. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Senior Learning Specialist position at oscar?
Click the "Apply Now" button on this page. You will be redirected to oscar's official application portal hosted on greenhouse where you can submit your application directly.
When was the Senior Learning Specialist job at oscar posted?
This Senior Learning Specialist position at oscar was posted on May 27, 2026. Apply as soon as possible — early applications are often reviewed first.
Senior Learning Specialist
oscar
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