Director of Technology

Please download the opportunity statement, which contains information about The Winsor 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

In the heart of Boston, less than a mile from Fenway Park, is an outstanding independent school that has been educating girls for nearly 140 years. The leader in girls’ education in Boston since 1886, The Winsor School has a rich history and an important mission: to prepare young women to pursue their aspirations and contribute to the world. Winsor is a vibrant community of students, teachers, families and staff who value intellectual curiosity, authentic engagement and personal integrity. Winsor challenges its 475 students in grades 5 through 12 to lead lives of purpose as responsible, generous-minded women. The school boasts a spectacular indoor/outdoor campus with modern facilities, an enviable location, and a national reputation for academic excellence, top-notch arts and athletics programs, and a commitment to belonging, support, and personal growth.

This summer, Winsor will welcome a new director of technology to oversee a mission-critical department that includes three other full-time dedicated professionals. At Winsor, the Technology Department plays an essential role in all aspects of school operations: supporting technology integration into classes and other co-curricular programs; deploying and maintaining a suite of enterprise database systems, and managing the critical IT infrastructure. The current director of technology oversaw a nearly complete rebuild of the backend infrastructure. At the same time, he and the department have built authentic, personal relationships with faculty, staff, and administrators. Thus, when the new director takes the helm this July, the next chapter of technology at Winsor will have a solid foundation from which to build and grow.

While Winsor has invested heavily in its technology program to ensure that students and teachers have access to state-of-the-art tools, hardware, and software, the school prioritizes human interaction, student engagement, and faculty/student relationships. Thus, the right next director will appreciate the importance of letting teachers find the right balance of technology usage—while still helping the leadership team and others to research and investigate emerging opportunities. On that note: Winsor has a robust STEM program in the Lower School, much of which runs through the school’s Innovation lab. While this academic department does not report up to the director of technology, all members of the technology team are essential partners to the success of this applied technology program. The next director’s arrival will coincide with the installation of Winsor’s next head of school. In December, the current associate director of technology, who functions primarily on the network and systems side of the house, will step down after 10 years at Winsor to pursue new opportunities. The timing of this transition will ensure a seamless onboarding experience for the director of technology, and give the director an opportunity to evaluate the departmental structure and make a key internal hire. To further ensure a smooth opening to the school year, Winsor would like the next director to start on or before July 1—so that there is no gap in departmental leadership with the outgoing director. The director of technology reports directly to the head of school and is a member of the senior leadership team.

IMPORTANT INFORMATION

Priority Deadline: April 7, 2025
Remote Semifinal Round: Weeks of April 21 & 28
On-site Final Round: Week of May 5
Decision Announced: May 16, 2025
Start Date: On or before July 1, 2025
Salary Range: $160,000–$200,000
Reports To: Head of School
Classification: Full-time, Exempt