Director, Strategic Planning, Office of the CEO
Oscar Health · New York, New York, United States
Posted 21 days ago · $198,720 - $260,820
or apply directly on Oscar Health's site. We never take the application ourselves.
Is this posting real?
- This role has been open
- 21 days Oscar Health's roles stay open a median of 41 days
- Reposted
- No
- Salary listed
- Yes 90% of Oscar Health's roles list one
- Ghost-job risk at Oscar Health
- low 0 stale, 9 reposted of 303 open
- Hiring momentum
- 439 roles opened in the last 90 days ↑ up vs. the prior 90 days
- Last confirmed on the employer's board
- 2026-09-17
Measured from postings appearing on and disappearing from Oscar Health's own greenhouse board since 2026-08-03. Full hiring picture for Oscar Health.
About this role
The Director of Strategic Planning for the Office of the CEO at Oscar will lead the development and execution of the company's strategy by partnering with various teams to align enterprise priorities with leadership decision-making. This role involves synthesizing complex issues, creating executive-ready narratives, and building planning structures to facilitate clarity and accountability as the company scales. The position requires a hybrid work schedule with three days in the office each week.
- benefits
- 5/5
- freshness
- 4/5
- career value
- 4/5
- role clarity
- 5/5
- pay transparency
- 5/5
Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Oscar Health as an employer.
What you need
- 10+ years of experience in strategy, business operations, corporate planning, chief of staff, or related roles
- 8+ years of experience developing executive presentations, board materials, strategic recommendations, or business cases for senior leadership
- 6+ years of experience supporting executive leadership, corporate strategy, business operations, or enterprise planning initiatives in a cross-functional environment
- Demonstrated experience designing or improving strategic planning processes, operating cadences, governance frameworks, or cross-functional operating models
- 6+ years of experience leading complex, cross-functional initiatives involving multiple stakeholders and competing priorities
- 4+ years of experience partnering with senior executives to drive strategic initiatives, organizational planning, or business transformation efforts
Nice to have
- MBA or equivalent graduate business training preferred; recent MBA graduates with relevant strategy experience are encouraged
- Healthcare, insurance, technology, or regulated industry experience preferred.
What you get
- Base pay of $198,720 - $260,820 per year
- Participation in Oscar's unlimited vacation program
- Company equity grants
- Annual performance bonuses
- Medical, dental, and vision benefits
- 11 paid holidays
Worth weighing
- Hybrid work schedule requires three days in the office each week, including mandatory in-office Thursdays.
- Role involves high-level strategic responsibilities, which may lead to significant pressure and expectations.
- Experience in fast-paced and highly regulated environments is necessary, indicating a potentially challenging work atmosphere.
Summarised from Oscar Health's posting. Read the full original.
Listed by Oscar Health on their greenhouse job board, last confirmed open on 2026-09-17. PitchMeAI is not the employer.
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