Director Windward Jobs (NOW HIRING)

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.

12M & Ed Tech Recruiting is running the search on behalf of Windward. Applications received by May 22 will receive priority review. For application instructions and the full job opportunity statement, please visit:

www.12MRecruiting.com/jobs/Windward/WI

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

SPECIFIC DUTIES

Strategic Planning & Leadership

• Articulate and lead a long-term vision for The Windward Institute that advances the Institute’s mission through research-based professional development, community education, outreach, and thought leadership in literacy, language-based learning disabilities, executive function skills, and related fields.
• Establish measurable goals and objectives that balance mission impact with revenue growth and financial sustainability, and track progress regularly to ensure accountability.
• Anticipate and adapt to changes in the educational landscape, using data and market insights to integrate innovative approaches that support the Institute’s role as a relevant and competitive leader in the field.
• Collaborate with other school leaders to align Institute programs and resources with institutional priorities.
• Represent the Institute’s vision and priorities to trustees, advisory board members, donors, and other key stakeholders.

Program & Services Development

• Oversee the design, quality, and implementation of the Institute’s research-based professional learning programs, including courses, workshops, school-based professional development, READ podcast series, and community education.
• Direct the development of asynchronous learning modules, including setting the vision and learning objectives; overseeing development and pilot-testing; and leading the plans for successful launch, integration, and long-term sustainability.
• Ensure all programming reflects current research and evidence-based practices in literacy, dyslexia, learning disabilities, executive function, and related fields.
• Regularly assess the Institute’s portfolio of programs to identify opportunities for innovation and growth to remain competitive in a changing educational landscape.
• Maintain accreditation and credentialing requirements for online learning modules, including relevant vendor applications.

Revenue Growth, Partnerships & External Engagement

• Develop and implement a long-term revenue growth strategy to expand the Institute’s financial sustainability.
• Partner with the advancement team to pursue grants and other philanthropic gifts for the Institute, including donor stewardship and engagement, and reporting requirements.
• Cultivate new and existing partnerships with schools, universities, corporations, nonprofits, and other organizations, and identify opportunities to increase the Institute’s visibility and community impact.
• Serve as a public spokesperson, brand ambassador, and thought leader for the Windward Institute by developing presentations, writing and editing publications, leading outreach events, and empowering colleagues to develop and share relevant content about the Institute.
• Collaborate with the marketing and communications team to strategize targeted marketing campaigns to bring asynchronous learning modules and other services to market.
  

Operations & Administrative Oversight

• Lead day-to-day operational oversight for the Institute, ensuring initiatives progress on clear timelines and within available resources.
• Supervise and provide outstanding mentorship, feedback, support, and professional growth to a team of approximately six full-time employees; and oversee recruitment and engagement of faculty, consultants, and contractors as needed.
• Oversee budgeting, pricing strategy for programs and modules, and vendor relationships in partnership with the CFO.
• Track and analyze program data to assess reach, effectiveness, and impact, and use insights to refine offerings and inform strategy.
• Serve as a key liaison to the board of trustees, Institute advisory board members, and school leadership, providing regular communications and updates, and cultivating potential members.
• Report directly to the head of school, and perform other duties as assigned.

QUALIFICATIONS

Qualifications

• Proven experience in nonprofit leadership, with the ability to balance mission, impact, and financial sustainability while leading teams through growth and change
• Advanced degree in educational leadership, management, or organizational development, or equivalent professional experience demonstrating high-level strategic and organizational leadership
• Deep knowledge of literacy, dyslexia, and other learning disabilities; ability to translate research into practice and stay current with emerging findings
• Business and operational expertise, including budgeting, pricing, vendor management, and revenue growth planning
• Demonstrated experience managing and scaling a growing organization, including building teams, improving systems and processes, and guiding organizations through periods of expansion and increased demand
• A track record of cultivating partnerships, expanding services, and supporting fundraising through grants, foundations, and philanthropic gifts
• Familiarity with marketing strategy and analytics, with the ability to collaborate on campaigns and adapt plans to ensure competitiveness

Qualities

• A strategic and entrepreneurial mindset, and a genuine excitement for developing and expanding the offerings of a research-based Institute
• Outstanding collaboration and team-building skills, with the ability to lead and inspire teams to deliver high-quality work on time, within budget, and in alignment with a shared strategic vision
• Exceptional communication skills, with the ability to deliver presentations to large groups and write effectively across varied formats
• A relational approach to cultivating positive and productive relationships with external partners, vendors, educators, and donors
• Humility, warmth, and collegiality that extends to internal and external stakeholders of a mission-driven organization
• A passion for serving and empowering educators within literacy and special education
• The ability to manage ambiguity with flexibility and adaptability

TO APPLY

For more information please visit the following link, which contains the job opportunity statement and complete application instructions.

www.12MRecruiting.com/jobs/Windward/WI