Chief of Staff

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

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.

About the role:

The Senior Director, Chief of Staff enables the departmental senior leadership team in shaping strategy, influencing the course the department will take to maximize enterprise value and growth in a way that is aligned with the mission of the company. This high-performing leader shapes the long-term strategy of the company by evaluating and executing strategic projects, deriving insights from external and internal research, and developing recommendations and scenarios in partnership with the senior team.

You will report into the EVP, President of Oscar Insurance.

Work Location: 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

Pay Transparency: The base pay for this role is: $218,592- $286,902 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities:

• In partnership with the senior leadership team, shape multi-year department strategy
• Own and manage the departmental enterprise budget in partnership with financial planning & analysis (FP&A) team
• Plan, organize, and lead team operating model including managing corporate strategic planning cycle as well as key team and leadership wide meetings
• Prepare material for leadership, operations team wide, MC/OpCo, and BoD meetings
• Lead the execution of multiple simultaneous strategy initiatives, which will be surfaced to the executive team and the board
• Collaborate deeply with SMEs and leaders across the organization
• Develop thorough and analytical business cases, including complex economic modeling, scenario development, risks, trade-off evaluation, and prioritization decisions - tying opportunities back to Oscar and our differentiation to ensure we appropriately assess our right to win
• Coach, develop and lead Executive Assistant(s) to achieve successful outcomes
• Communicate the established strategy to the organization in partnership with our Communications and leadership team
• Drive change management across the department in alignment with department and/or company strategy
• Assemble and maintain a foundation of intelligence - e.g., business financials / competitive data - that can serve as a fact base for projects and discussions
• Serve as a proxy for Management Committee leader, when needed
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• A bachelor's degree or commensurate 4 years of experience
• 15+ years experience, with 10+ of those years in healthcare consulting or a strategic role in the healthcare industry
• 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’s degree from top-tier program in business, health administration, or related field