Director of The Windward Institute
Please download the opportunity statement, which contains information about The Windward School and the position, as well as required application materials to prepare in advance. All applications must be submitted online. Please review the How to Apply section below for further application instructions.
SUMMARY
The Windward School is a premier coeducational, independent day school in the New York City Metropolitan Area that serves children with language-based learning disabilities (LBLD) in grades one through nine. Windward is a large enterprise with three campuses, two in White Plains and one in Manhattan. Over 400 part-time and full-time faculty and staff work with one primary focus: to help nearly 1,000 students achieve their full potential in preparation for a successful return to a mainstream educational environment.
At this pivotal moment, The Windward School seeks a director of the Windward Institute to guide and implement its mission and lead the Institute into its next chapter of growth and impact. Since its formation in 2019, the Institute has built deep content expertise, meaningful partnerships, and a tangible impact in the lives of children and families—including three free reading screenings a year in underserved communities, a podcast reaching 130+ countries, and a robust range of professional development courses and workshops.
The WI is now at an exciting inflection point: it has deep content expertise, excellent programs, and meaningful partnerships, and can leverage this foundation and increasingly philanthropic investments to become more strategically positioned in a rapidly changing educational marketplace. The next director will be charged with building toward the future: an entrepreneurial, growth-oriented, technology-forward operation that actively cultivates new markets, partnerships, and revenue streams to scale its impact while preserving the human connection that makes The Windward Institute’s approach so transformative.
The director will lead a collaborative team of six full-time staff members, working in close partnership with the head of school, board of trustees, and other community members to advance the Institute’s impact. Key priorities include identifying strategic market opportunities, leveraging technology to expand reach, cultivating partnerships with experts in the LBLD field, and ensuring financial sustainability for the Institute. The director of The Windward Institute will report to the head of school, and will start later this summer.
IMPORTANT INFORMATION
Priority Deadline: May 22, 2026
Application Review: Late May to Early June
On-site Final Round: Mid-to-late June
Start Date: Summer 2026
Reports To: Head of School
Classification: Full-time, Exempt
Annual Salary Range: $300,000–$325,000
We invite you to watch our interview with Jamie Williamson, Head of School at Windward, who talks about Windward's mission, his passion for leading a school that supports students with LBLD, the impact of the Windward Institute (WI) both externally and internally to Windward, and the vision for the next chapter of the WI.
We invite you to watch our interview with Jamie Williamson, Head of School at Windward, who talks about Windward's mission, his passion for leading a school that supports students with LBLD, the impact of the Windward Institute (WI) both externally and internally to Windward, and the vision for the next chapter of the WI.
How to Apply
- If you have not done so already, download the opportunity statement.
- Prepare your application materials, which are described on the last page of the opportunity statement.
- Click on Apply Now, which will take you to our application portal, where all applications will be processed.
- Follow the instructions on that application portal to upload your documents.
- Applications received on or before May 22 will receive priority review.