Chief Technology Officer

Town now seeks a chief technology officer (CTO) to start this summer. Reporting directly to the head of school, the CTO will serve as a senior administrator and lead the school’s technology strategy with a focus on what matters most in a K-8 community: age-appropriate educational practice, dependable service, and smooth day-to-day operations. This new role offers meaningful room to shape how technology is chosen, supported, and communicated so that it remains purposeful and age-appropriate for boys, and dependable and easy to use for faculty, staff, and families. The successful candidate will bring a community-minded, service-oriented leadership style, sound judgment, and the range to guide educational technology and core systems with clarity and care, along with the technical grounding to steward secure, reliable infrastructure and responsible risk management. The CTO will supervise the director of educational technology, the network administrator, and a part-time help desk staff member.

12M & Ed Tech Recruiting is running the search on behalf of Town School for Boys. Applications received by March 13 will receive priority review. For application instructions and the full job opportunity statement, please visit:

https://www.townschool.com/employment, * Serve as Town’s senior technology leader, reporting to the head of school and contributing to school-wide planning and decision-making.

• Supervise the director of educational technology, the network administrator, and part-time help desk support, setting clear priorities and expectations.
• Communicate technology plans and decisions with clarity to faculty, staff, families, and trustees as appropriate.
• Model a school-centered approach to technology leadership, grounding decisions in student experience, faculty practice, and the daily life of the community.
• Participate actively in school life as a visible member of the community and perform other duties as assigned.

Educational Technology

• Provide direction for educational technology through the director of educational technology, in close collaboration with division leadership and the director of teaching, learning, and innovation.
• Advance faculty support and shared practices for instructional tools in ways that fit Town’s program, values, and students’ developmental needs.
• Help the school establish clear, practical guidance for emerging tools, including AI, and communicate that guidance effectively to families and faculty.

Systems & Data

• Provide oversight of Town’s core systems environment, including the ongoing stewardship of Veracross after transition.
• Guide planning for how key platforms and workflows connect with Veracross over time, coordinating internal stakeholders and vendors as needed.
• Promote sound data practices and reporting routines that support daily operations and informed decision-making.

Infrastructure, Security, & Reliability

• Oversee network and systems reliability, lifecycle planning, and campus technology needs, including AV and shared spaces.
• Guide cybersecurity, privacy, and risk management practices appropriate to a school environment, including readiness planning and vendor oversight.
• Lead technology budgeting and multi-year planning for upgrades and replacements.

• Bachelor’s degree required; advanced degree and/or relevant certifications preferred
• 5+ years of progressive technology leadership experience, including senior-level responsibility for systems, infrastructure, and cybersecurity (school or similarly mission-driven environment preferred)
• 5+ years of people management experience, including hiring, coaching, and performance management
• Demonstrated experience overseeing network and core systems operations, enterprise platform integrations including SIS-related systems, and cybersecurity and risk management, even if prior experience in these areas is not equal
• Experience managing budgets, contracts, and multi-year planning, including refresh cycles and project delivery

Leadership and Personal Qualities

• A collaborative leader who builds shared direction across academic and operational teams
• Clear communicator with the ability to translate between technical detail and day-to-day school needs
• Sound judgment and disciplined prioritization in a fast-moving environment
• Steady, service-oriented approach that supports reliability, responsiveness, and user experience
• Commitment to fostering belonging and leading technology practices that support an inclusive community
• Willingness to participate in the life of the school, including occasional schoolwide events outside the regular day

Since its founding in 1939, Town School for Boys has specialized in educating, nurturing, and celebrating boys. Town provides a rich, challenging, and rigorous educational experience that directly serves the distinctive learning styles, energy levels, and developmental needs of boys in grades K-8. The school cultivates integrity, sensitivity, empathy, and respect in its boys; values diversity, equity, and inclusion; and prepares students to become productive citizens of a constantly evolving world. Town’s faculty and staff are dedicated to advancing the school’s mission, philosophy and core values. Distinguishing features of Town School include its engaging curricula, warm faculty and staff, supportive parent network, and the diversity of interests and backgrounds represented in its student and alumni bodies.