Chief of Staff
Windward School•White Plains, NY
About The Position
The Chief of Staff serves as a senior strategic advisor and execution partner to the Head of School and Executive Cabinet. This role acts as a force multiplier for leadership—translating vision into action, driving alignment across the organization, and ensuring the successful execution of the school’s highest priorities. Operating at the intersection of strategy, operations, and leadership, the Chief of Staff leads complex cross-functional initiatives, strengthens organizational systems, and enhances institutional effectiveness.
Requirements
- 10+ years of experience in strategy, operations, consulting, or leadership roles
- Experience leading complex, cross-functional initiatives
- Strong strategic thinking and problem-solving skills
- Excellent communication and interpersonal abilities
- High emotional intelligence and sound judgment
- Commitment to the mission of supporting students with learning differences
Responsibilities
- Partner with the Head of School and Board to support strategic planning and long-term vision
- Translate priorities into actionable plans with clear metrics, timelines, and ownership
- Develop and track KPIs and institutional dashboards
- Lead regular progress reviews and reporting
- Serve as a strategic advisor to the Head of School and Executive Cabinet
- Design and manage leadership operating rhythms and meeting structures
- Ensure alignment between institutional priorities and departmental plans
- Support decision-making through analysis and structured problem-solving
- Lead high-priority, cross-functional initiatives
- Drive projects from concept through execution
- Remove barriers and manage risks
- Coordinate across academic, operational, and administrative teams
- Build systems to monitor progress against goals
- Standardize planning and reporting processes
- Analyze data to improve effectiveness
- Strengthen accountability across the organization
- Improve systems, workflows, and policies
- Partner with HR on organizational design and evaluation systems
- Support onboarding and talent development
- Collaborate with technology teams to enhance tools and systems
- Ensure clear communication of priorities and progress
- Support Head of School communications
- Promote transparency and alignment across the organization
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
Number of Employees
101-250 employees
