Director of Technology (Boston, MA)

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 15 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.

12M & Ed Tech Recruiting is running the search on behalf of Winsor.  Applications received by April 7 will receive priority review.  For application instructions and the full job opportunity statement, please visit www.EdTechRecruiting.com/jobs/Winsor/technology.

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
Reports To: Head of School
Classification: Full-time, Exempt

DUTIES

Strategic Leadership

• Develop and implement a forward-looking technology vision aligned with the school’s mission, values, and strategic priorities.
• Collaborate with academic, administrative, and operational leadership to ensure technology supports innovation, efficiency, and the broader goals of Winsor.
• Develop and manage the technology budget, ensuring cost-effective and efficient use of resources.
• Develop and enforce IT policies and procedures to ensure compliance with legal and regulatory requirements.
• Establish and maintain partnerships locally and nationally to advance the school’s technology objectives.
• Serve as a member of the leadership team, report directly to the head of school, and perform other duties as assigned.

• Collaborate with faculty and staff to integrate instructional technology tools, including AI-based solutions, to enhance teaching and learning.
• Provide professional development opportunities to help faculty effectively utilize technology for innovation and efficiency in the classroom.
• Partner with academic leaders to design and execute a strategic vision for instructional technology aligned with the school’s mission.
• Explore and assess new teaching and learning approaches through technology, fostering a culture of continuous improvement and innovation.

• Oversee the school’s enterprise data environment, including the school’s chosen LMS and SIS platforms, ensuring secure and effective use across all departments.
• Evaluate current data workflows, providing recommendations and implementing changes to enhance reporting and accessibility for end-users across the school.
• Coordinate the integration of various technology systems to ensure seamless operation and communication between different platforms.
• Partner with school leaders to ensure data supports decision-making across key areas, including admissions, advancement, and academics.
• Lead enterprise-wide data projects, coordinating with internal teams and external vendors to achieve successful outcomes.

• Oversee the technology department, supervising a team of three other full-time staff members and supporting their professional growth through a collaborative leadership approach.
• Manage the deployment and maintenance of hardware, software, and infrastructure to ensure performance, cost-effectiveness, and scalability.
• Regularly review IT security protocols, disaster recovery plans, and risk management strategies to safeguard the school’s digital assets.
• Evaluate current systems and services to identify opportunities for improvement in service delivery and operational efficiency.
• Manage a helpdesk system to track and resolve technical issues.
• Work with the systems integration and technology support specialist, who report to the director of technology, to troubleshoot and resolve technical issues.

• Bachelor’s degree from an accredited college or university in information technology, computer science, educational technology, or a related field (master’s degree preferred)
• At least five years of leadership experience in managing technology departments and supervising technology staff, preferably in educational or nonprofit settings
• Proficiency in key areas of technology management, including enterprise IT, instructional technology, data systems, and client services
• A demonstrated ability to design, implement, and oversee impactful instructional technology programs
• Experience in successfully leading concurrent technology-related programs and projects, with a proven ability to set priorities and deliver results
• Expertise in fostering team growth, managing change, and setting strategic goals for a dynamic and collaborative department

• A collaborative and empathetic leader who values teamwork and cultivates a culture of inclusivity
• A passion for managing diverse areas of technology—including infrastructure, instructional integration, and data systems—even if prior experience in these areas varies
• Exemplary communication skills, including the ability to effectively convey ideas, inspire confidence, and engage a wide range of stakeholders
• Skill in building consensus, facilitating critical discussions, and guiding institutions through transitions or new initiatives
• A demonstrated commitment to advancing community and inclusion through both personal engagement and practical implementation
• The ability to think strategically while addressing immediate needs, combining vision with attention to detail
• A deep commitment to girls’ education, supporting an inclusive and empowering learning environment that fosters innovation, collaboration, and academic excellence.
• A sense of humor and flexibility, as well as a genuine appreciation for working with adolescents, fostering positive relationships and creating an engaging and supportive school environment.
• An eagerness to participate in the life and activities of an independent school, which will include occasional evening or weekend events

The Winsor School is an equal opportunity employer and will not discriminate against any applicant for employment on the basis of race, color, religion, gender, age, national origin, marital status, sexual orientation, genetic testing, veteran status, physical or mental disability, or on any other basis protected by law.

Department: Administration
This is a management position
This is a full time position