Pine Cobble School seeks candidates for a Director of Information Technology.  This is a full-time, 12-month position beginning on August 1, 2026.

Pine Cobble School is a close-knit, mission-driven independent school serving students from Beginners through Grade 8. Rooted in progressive education, Pine Cobble emphasizes experiential learning, strong relationships, and the development of the whole child. Located in Williamstown, Massachusetts, the school benefits from the cultural, educational, and natural resources of the Berkshire region.  Pine Cobble seeks a strategic, collaborative, and forward-thinking Director of Information Technology to lead the vision, planning, and implementation of all technology systems across the school.

Job Summary 

The Director of Information Technology plays a critical leadership role in ensuring that Pine Cobble’s technology infrastructure, systems, and practices support excellent teaching and learning, effective operations, and a safe, secure campus environment. This position requires both strategic oversight and hands-on leadership, with an emphasis on continuous learning, thoughtful implementation, and clear communication with all school constituencies.

Pine Cobble School is committed to equity and justice. Indeed, we have made this a core priority in our strategic plan. This work is critically important — for all of our students, for our institution, and for the world that our students will someday lead. We approach our work and learning with care and compassion for each other, ourselves, the greater community, and our natural environment. We strive to create an effective learning environment that engages learners and supports their unique learning styles, allowing them to acquire new skills in a way that maximizes understanding and retention.  This extends to our use of technology; we strive to incorporate technology into the learning process when it enhances the capacity for student learning and/or affords opportunities for creativity.  The Director of IT will guide discussions on best practices for technology integration and curricula for developing digital wellness and preparedness in our students. 

Duties and Responsibilities

Strategic Leadership & Planning

• Develop and implement a comprehensive, long-term technology strategy aligned with Pine Cobble School’s mission, educational philosophy, and strategic goals.
• Evaluate emerging technologies and best practices to ensure systems are scalable, sustainable, and responsive to the evolving needs of students, faculty, and staff.
• Serve as a strategic partner to school leadership on technology-related decision-making, budgeting, and risk management.

Systems & Infrastructure

• Oversee all school technology systems, including network infrastructure, servers, cloud services, hardware, and software platforms.
• Ensure reliability, performance, and security of all systems supporting academic and administrative functions.
• Lead lifecycle planning for hardware and software, including purchasing, deployment, maintenance, and replacement.
  
  

Security & Data Protection

• Direct all aspects of information security, data privacy, and compliance, including cybersecurity protocols, access controls, backups, and disaster recovery planning.
• Oversee physical and digital security systems, including campus security technology, cameras, access systems, and coordination with emergency response plans.
• Establish and maintain policies and training related to data security and responsible technology use.
  
  

Communications & Emergency Systems

• Manage and optimize all school communications systems, including phones, internal communication platforms, and emergency notification systems.
• Ensure that emergency communication processes are reliable, well-documented, and regularly tested.
• Collaborate with school leadership to support crisis preparedness and response from a technology perspective.
  
  

Teaching, Learning & Professional Growth

• Support faculty and staff in the effective and thoughtful use of technology for teaching, learning, and school operations.
• Provide training, documentation, and professional development that builds confidence and capacity across the community.
• Foster a culture of continuous learning and improvement around technology use.
  
  

Management & Collaboration

• Manage technology vendors, consultants, and service providers.
• Develop and manage the technology budget with transparency and fiscal responsibility.
• Collaborate closely with administrators, faculty, staff, and families to ensure technology systems meet community needs.
  
  

Application Process

Interested candidates should submit a cover letter, résumé, and list of 3 references to Ellen Sutherland, Director of Human Resources at Pine Cobble School (e.sutherland@pinecobble.org)

Applications will be reviewed on a rolling basis until the position is filled.

Pine Cobble School is committed to recruiting and supporting a diverse faculty and staff and maintaining a workplace culture in which all are treated equitably; we encourage applications from candidates who will contribute to the diversity and vitality of the school community.  

Qualifications

• Bachelor’s degree required; advanced degree or relevant certifications preferred.
• Significant experience in information technology leadership, ideally within an educational or mission-driven organization.
• Demonstrated expertise in network infrastructure, cybersecurity, data systems, hardware/software management, and communications systems.
• Strong strategic thinking skills paired with the ability to implement and manage complex systems.
• Excellent communication, training, and relationship-building skills.

A collaborative, service-oriented mindset and commitment to supporting a school community.

About Pine Cobble School

Pine Cobble School, an independent Beginner through Grade 8 school rooted in progressive education and experiential learning. Pine Cobble School is committed to equity and justice. Indeed, we have made this a core priority in our strategic plan. This work is critically important — for all of our students, for our institution, and for the world that our students will someday lead. We approach our work and learning with care and compassion for each other, ourselves, the greater community, and our natural environment. We strive to create an effective learning environment that engages learners and supports their unique learning styles, allowing them to acquire new skills in a way that maximizes understanding and retention.

Connections working at Pine Cobble School