Sr. Executive Assistant

Oscar Health

Oscar Health

New York, NY, USA
Posted on Tuesday, August 15, 2023

Hi, we're Oscar. We're hiring a Senior Executive Assistant to join our Executive Assistant 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

Oscar’s Executive Assistants ensure tight operations and time management for our Senior leaders. Responsibilities include standard administrative duties, such as managing calendars, meetings, time prioritization and availability, VIP guests, travel planning, expenses, etc. It also includes independent management and oversight of overall administrative operations and support for your respective business segment. It may also include indirect management of other Executive Assistants within your business segment. Executive Assistants also serve as a link between business segments, making sure administrative and business office operations across the company are optimized and leverage best practices.

You will report to the EVP of +Oscar line of business.

This is a hybrid role. You will work part of the time in the New York City office and part of the time work-from-home/remote. #LI-Hybrid

The base pay for this role in the states of California, Connecticut, New Jersey, New York, and Washington is: $96,000 - $126,000 per year. The base pay for this role in all other locations is: $86,400 - $113,400 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program and annual performance bonuses.


  • Manage the executive's day-to-day calendar, including prioritization of sensitive matters
  • Support delivery of successful cross-functional processes
  • Manage senior leader travel and expense management processes, including travel arrangements and itineraries
  • Manage and maintain a range of meetings on behalf of your senior leaders, including 1:1s, client/vendor meetings, team meetings, town halls/all hands, etc.
  • Create & Manage process books/instructions for administrative processes that will be leveraged across your business segment & Executive Assistant team to work more effectively
  • Work with key roles in People, Finance, Workplace Operations, and IT to coordinate processes for your executive’s business office (e.g., onboarding)
  • Independently plan and manage in-person and virtual events and meetings aligned to the executive’s priorities


  • 7+ years of experience in a fast-paced office environment supporting senior level executive.

Bonus Points

  • Ability to independently and creatively problem-solve with nominal supervision
  • Ability to effectively manage upwards your executive and senior leaders
  • Ability to act as gatekeeper and escalate relevant information to executives as needed
  • Excellent time management, including the ability to meet deadlines or escalate in a timely manner & with an emphasis on proactively identifying opportunities for improved efficiency
  • Excellent verbal and written communication skills
  • Strong organizational skills and ability to multitask with ever-changing priorities
  • Strong interpersonal and relationship management skills
  • Ability to treat confidential information with exceptionally high discretion
  • Exceptional attention to detail
  • Proficiency of office software (e.g., calendars, docs, spreadsheets, virtual meetings) including teaching others knowledge

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.

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 ( to make the need for an accommodation known.