Chief of Staff

Oscar Health
New York, New York, United States$181k – $237kPosted 27 February 2026

Job Description

<p>Hi, we're Oscar. We're hiring a Chief of Staff to join our team.</p> <p>Oscar is the first health insurance company built around a full stack technology platform and a relentless 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.</p> <p><strong>About the role:</strong></p> <p>You will drive the economic flywheel for the Insurance and Operations business across strategic planning, operational execution and talent strategy to ensure business achieves its objectives. 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 drive annual corporate business processes, in partnership with corporate strategy, including long term strategy and operating plan annual development and implementation</p> <p>You will report into the EVP, President of Oscar Insurance.</p> <p><strong>Work Location: </strong>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</p> <p><strong>Pay Transparency: </strong>The base pay for this role is: $180,504 - $236,911 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.</p> <p><strong>Responsibilities:</strong></p> <ul> <li>Shape multi-year department strategy in partnership with the leadership team</li> <li>Drive departmental efficiencies through process improvements and workforce optimization initiatives</li> <li>Facilitate and provide leadership on cross-functional processes to drive efficiency in partnership with subject matter experts (i.e., performance management, FPA, budget reporting, and tech)</li> <li>Prioritize competing initiatives and projects. Create decision-making frameworks that help prioritize critical tasks for leadership</li> <li>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</li> <li>Drive various department-wide forums, including owning agendas and ensuring the smooth running of the forum and thoughtful discussion on key topics</li> <li>Manage preparation for and execution of governance meetings owned by the leader including aggregating, evaluating, and tracking department vitals and KPIs</li> <li>Partner with the People Team to drive staff talent development and organization structure across the organization</li> <li>Compliance with all applicable laws and regulations</li> <li>Other duties as assigned</li> </ul> <p><strong>Requirements:</strong></p> <ul> <li>Bachelor's degree or commensurate 4 years of experience</li> <li>10+ years experience, with 5+ of those years in healthcare consulting or a strategic role in the healthcare industry</li> <li>5+ years experience collaborating and influencing at the executive level</li> <li>5+ years experience defining and deploying strategies for organizations at the company level</li> </ul> <p><strong>Bonus points:</strong></p> <ul> <li>Master's degree from top-tier program in business, health administration, or related field</li> </ul><div class="content-conclusion"><p><span style="font-weight: 400;">This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud</span><a href="http://hioscar.com/careers/recruitment-fraud-alert"><span style="font-weight: 400;"> </span><span style="font-weight: 400;">here</span></a><span style="font-weight: 400;">. </span></p> <p><span style="font-weight: 400;">At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiri ... (truncated, view full listing at source)