About the job
Welcome to Oscar! We are actively seeking a Chief of Staff to become a vital part of our innovative team.
Oscar stands out as the first health insurance company designed around a holistic technology platform, emphasizing a commitment to our members' well-being. Founded in 2012, we aim to redefine health insurance by providing an experience akin to having a family doctor.
About the Role:
In this position, you will lead the economic engine of our Insurance and Operations business through strategic planning, operational execution, and talent management, ensuring we meet our business goals. Collaborating with leaders company-wide, including Chief of Staff counterparts for other executives, you will tackle complex challenges, implement actionable solutions, and coordinate operational initiatives. You will oversee the annual corporate business processes, working closely with corporate strategy to develop and implement long-term strategies and operational plans.
You will report directly to the EVP, President of Oscar Insurance.
Work Location: This role is based in our New York City office with a hybrid work model—requiring three days of in-office work each week. Thursdays are designated in-office days for team meetings and events, while the other two days are flexible to accommodate your schedule. #LI-Hybrid
Pay Transparency: The base salary for this position ranges from $180,504 to $236,911 annually. You will also be eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.
Responsibilities:
- Develop multi-year departmental strategies in collaboration with the leadership team.
- Enhance departmental efficiencies through process improvements and workforce optimization initiatives.
- Lead and facilitate cross-functional processes to improve efficiency alongside subject matter experts (e.g., performance management, FP&A, budget reporting, and technology).
- Prioritize competing initiatives and projects, creating decision-making frameworks that assist leadership in focusing on critical tasks.
- Act as a representative for leadership as needed, attending meetings and calls, ensuring they are well-prepared with relevant materials.
- Oversee various department-wide forums, including managing agendas and fostering meaningful discussions on key topics.
- Prepare for and execute governance meetings, including aggregating, evaluating, and tracking departmental vitals and KPIs.
- Collaborate with the People Team to enhance staff talent acquisition and retention strategies.

