Hi, we're Oscar. We're hiring a Senior Chief of Staff to join our Technology 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

In this role, you will enable the departmental senior leadership team across our technology organization (Engineering, Product, Data, Security) in developing long-term strategies by evaluating and executing strategic projects, deriving insights from external and internal research, and developing recommendations and scenarios in partnership with the senior leadership team. You will partner with leaders across the company, including Chief of Staff roles for other executives, to solve complex problems, drive solutions, and orchestrate operational initiatives. You will run the business office processes (objectives and key results, workforce planning, etc) and work closely with departmental leadership to develop strategic solutions to address market dynamics and achieve corporate goals.

You will report to the Chief Product Officer.

Work Location: 

Oscar is a blended work culture where everyone, regardless of work type or location, feels connected to their teammates, our culture and our mission.

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

Pay Transparency:

The base pay for this role is: $174,400 - $228,900 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants, and annual performance bonuses.

 

Responsibilities

  • Shape multi-year department strategy in partnership with the leadership team
  • Drive departmental efficiencies through process improvements
  • Facilitate and provide leadership on cross-functional processes to drive efficiency in partnership with subject matter experts (i.e., performance management, FP&A, budget reporting)
  • Prioritize competing initiatives and projects. Create decision-making frameworks that help prioritize critical tasks for leadership
  • Serve as a proxy for leadership as needed, including attending meetings and calls and ensure leadership is prepared for meetings with appropriate pre-reads and context
  • Drive various department-wide forums, including owning agendas and ensuring the smooth running of the forum and thoughtful discussion on key topics
  • Manage preparation for and execution of governance meetings owned by the leader including aggregating, evaluating, and tracking department vitals and KPIs
  • Partner with the People Team to drive staff development across the organization
  • Compliance with all applicable laws and regulations
  • Other duties as assigned 

Qualifications

  • Bachelor's degree or commensurate 4 years of experience
  • 10+ years experience, with 5+ of those years in healthcare consulting or a strategic role in the healthcare industry
  • 5+ years experience collaborating and influencing at the executive level
  • 5+ years experience defining and deploying strategies for organizations at the company level

Bonus Points

  • Master’s degree from top-tier program in business, health administration, or related field 

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 (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 Notice to Job Applicants.

Apply for this Job

* Required
resume chosen  
Dropbox
(File types: pdf, doc, docx, txt, rtf)
Cancel
cover_letter chosen  
Dropbox
(File types: pdf, doc, docx, txt, rtf)
Cancel

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Oscar Health’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.

Enter the verification code sent to to confirm you are not a robot, then submit your application.

This application was flagged as potential bot traffic. To resubmit your application, turn off any VPNs, clear the browser's cache and cookies, or try another browser. If you still can't submit it, contact our support team through the help center.