Senior Director, Office of the CEO

Hi, we're Oscar. We're hiring a Senior Director, Office of the CEO to join our 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

The Sr. Director, Office of the CEO is critical in supporting and mobilizing our Executive Team’s strategic vision and ensuring operational excellence across the organization. This leader will drive the CEO’s core governance forums, execute discretionary strategic projects, and engage key internal and external stakeholders on behalf of the Executive Office. A strong analytical background and ability to rationalize business cases and organizational trade-offs is paramount for success in this role. The ideal candidate will possess strong leadership skills, exceptional communication abilities, and a deep understanding of corporate strategy and governance. This role will report into the EVP, Chief of Staff to CEO.

You will report to the Chief of Staff to the CEO.

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. 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: $211,200 - $277,200 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities

• Drive and manage the Executive Office’s key governance forums, ensuring effective communication and decision-making among executive leadership. Prepare agendas, facilitate discussions, and ensure follow-up on action items to promote accountability.
• Collaborate with the Executive Office to develop and implement key organizational initiatives. Provide insights and recommendations based on strategic analyses.
• Oversee high-priority discretionary projects, ensuring alignment with company objectives and multi-year strategy
• Plan, organize, and manage the corporate business cycle, including key company wide meetings and external engagements on behalf of the Executive Office
• Build and maintain relationships with key stakeholders, including executive leadership and external partners
• Represent the Executive Office in meetings and internal engagements as needed
• Drive change management across the Company in alignment with department and/or company strategy
• Own and manage the Executive Office’s enterprise budget in partnership with financial planning & analysis (FP&A) team 
• In partnership with the Corporate Strategy team, shape multi-year department strategy
• Prepare material for leadership, Management Committee, Operating Committee, and BoD meetings
• Collaborate deeply with SMEs and leaders across the organization
• Serve as a proxy for Chief of Staff, when needed
• Compliance with all applicable laws and regulations 
• Other duties as assigned

Qualifications

• A bachelor's degree or commensurate 4 years of experience
• 10+ years experience, with 8+ of those years in healthcare consulting or strategic finance
• 7+ 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 of Business Administration (MBA) from top-tier program