Chief Technology Officer

The Windward School - White Plains, New York - Full time


The Windward School is a premier co-educational, 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 are in White Plains, and one is 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.

Beyond its traditional school operations, Windward has an international reputation as being a leader in LBLD education. For many years, The Windward Institute and the Windward Teacher Training Program have played a huge role in advancing and improving LBLD instruction in public school districts and private schools throughout the world. Other schools have recently launched across the country, by following Windward’s highly successful model.

The chief technology officer (CTO) is a new role that comes at a key time for Windward. Historically, technology was not a huge component of day-to-day instructional practices at this school, where reading and writing instruction was built around a multisensory direct instruction approach that focused on the skill development and importance of handwriting. In addition, teacher training was also delivered in person for many years. Post pandemic, the school has not abandoned its roots, but at the same time it has recognized that technology has the potential to improve efficiencies and broaden the reach of the program. With the current head of school now in his fifth year, the technology program will be a cornerstone for the next chapter of this highly regarded educational institution approaching its centennial. Thus, the CTO will serve in the executive cabinet, which includes six other senior administrators with broad areas of oversight and responsibility.

The CTO will lead a department that currently has seven technology professionals working across the three campuses. Since the pandemic, the school has also worked with two different managed services providers to backfill support needs, major upgrades, and network engineering. The CTO will have the opportunity to evaluate how the department is structured and how each role is defined, while staying within the current FTE count of seven technology professionals plus the director. This new role reports directly to the head of school and starts this summer — or earlier by mutual agreement.

Ed Tech Recruiting is running the search on behalf of Windward. Applications submitted by February 11 will receive priority review. For application instructions and the full job opportunity statement, please visit:


Applications Accepted Starting: January 10, 2024

Priority Deadline: February 11, 2024

Application Review by Windward: Approximately late February to late March

Start Date: Late Spring / Early Summer

Reports To: Head of School

Salary Range: $200,000 to $220,000


Operations Oversight

Oversee IT/IS operations, planning, policies, and procedures within a management framework that serves a three-campus school.

Oversee and evaluate the deployment of all hardware, software, systems, back-end infrastructure, and services from various perspectives, including cost-effectiveness, customer satisfaction, compliance, asset management, quality of service, and performance.

Ensure that the department responds to end-user needs, provides a reliable IT backbone, designs and delivers excellent end-user training, and aligns procedures to all-school needs.

Ensure IT data security, risk management, disaster recovery, and planning processes are in place and receive regular review for currency and adequacy.

Academic, Administrative, and Operational Partnerships

Serve in the head of school’s executive cabinet, which comprises seven all-school administrators with broad areas of responsibility.

Maintain close working relationships with the School’s extended senior admin team, which comprises the executive cabinet plus five other directors who also report to the head of school.

In close partnership with the director of educational technology, who reports to the associate head of school for academic programs, ensure that the School has a thoughtful vision for technology that is aligned to the School’s overall strategic plan, mission, and values.

Build departmental connections with academic, administrative, and operational constituents throughout the School.

Establish and maintain local, regional, and national partnerships to support the strategic goals of the School’s technology program.

Departmental Administration

Oversee all operations involving IT infrastructure, data/systems, and help desk support by a three-campus technology department that currently includes seven professionals reporting to the CTO.

Allocate time and resources toward sustaining a positive departmental culture, including goal setting and team building, and ensure that each member of the department has an opportunity for professional growth.

Oversee the School’s outsourced engineering and managed services partners.

Manage the departmental budget and perform other duties as assigned.


Professional Qualifications

A bachelor’s degree from an accredited college or university is a minimum requirement, though a graduate degree is highly desirable

Director-level knowledge of departmental leadership, staff supervision and development, change management, and setting and achieving departmental goals

Experience in major areas of technology planning and administration, such as enterprise systems design and implementation, instructional technology leadership, dataflow and data interoperability, project management, fiscal planning and oversight, end-user training, and capital construction

Leadership and Personal Qualities

An enterprise approach to technology management that supports individual needs within a scalable framework for a large department at a three-campus school serving nearly 1,000 students

An ability to plan and oversee concurrent technology-related programs and projects, and empower departmental leads to ensure completion and success

A passion and interest for managing all areas of technology—IT, data/systems, and instructional—even if prior experiences in these areas are not equal

An ability to build consensus among diverse groups, facilitate critical discussions within large groups, and instill confidence in colleagues during times of transition

A thoughtful but determined approach to team building and staff development

Genuine commitment to growing formal leadership capacity and creating organizational and operational structures within a large department

Immersion in diversity work, both in training and in implementation

Inspirational and diplomatic leadership sensitive to the needs of a diverse faculty

A collaborative, cooperative, empathetic, collegial, innovative, and patient mindset

Exceptional communication skills: written, verbal, presentation, and training

An understanding of the diverse technology needs and organizational complexities of a large, high-achieving, multidivisional, independent school

A commitment to the mission and values of Windward, which serves children with language-based learning disabilities

Confidence and humility, together with a sense of humor and warm personality


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

The Windward School is an equal opportunity employer and makes employment decisions on the basis of merit and job performance. School policy prohibits discrimination based on race, color, creed, gender, gender identity or expression, religion, marital status, age, national origin or ancestry, physical or mental disability, medical conditions (including genetic characteristics or information), sexual orientation, or any other consideration made unlawful by federal, state, and local laws.

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C Level Executive Leadership

Experience Level

Senior Level

The Windward School

The Windward School is a premier co-educational, independent day school in the New York City Metropolitan Area that serves children with language-based learning disabilities (LBLD) in grades one through nine.
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