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.

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

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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.

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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.

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