Senior IT Leader: Education Tech Strategy & Ops

Milton Hershey School; Hershey (PA); On-site; USD 173,000 - 231,000; Full time

Job summary

Milton Hershey School in Hershey, PA, is seeking a Senior Director of Information Technology to lead a comprehensive, campus-wide technology ecosystem. The role focuses on strategy, security, infrastructure, and administrative and academic computing, with partnership across schools and operations to advance the school’s mission.

The on-site, full-time position requires a track record of leading enterprise IT initiatives, strong executive communication, and a commitment to student-centered

Qualifications

• 10+ years of technology leadership in large organizations.
• Experience leading enterprise IT operations and initiatives.
• Proven ability to develop and execute multi-year IT roadmaps.
• Experience with AI and automation adoption.
• Strong leadership and talent development.
• Strong financial, operational, and vendor management skills.
• Excellent communication with executives and stakeholders.
• Experience in education or complex educational organizations preferred.

Responsibilities

• Develop and execute a multi-year IT strategy and roadmap.
• Lead IT operations including infrastructure, security, and end user support.
• Mentor IT management staff and foster a customer-focused culture.
• Establish governance, standards, and long-range technology plans.
• Lead major technology initiatives with budgets and timelines.
• Drive efficiency, reliability, and value from technology investments.
• Improve user experience with service levels and partnerships.
• Oversee budgeting, procurement, contracts, and vendor management.
• Evaluate emerging technologies and cybersecurity considerations.

Skills

Technology leadership

Strategic planning

Executive communication

Team leadership

Cybersecurity governance

Vendor management

Education

Bachelor’s degree in IT/CS/Business

Master’s degree preferred

Job description

Milton Hershey School in Hershey, PA, is seeking a Senior Director of Information Technology to lead a comprehensive, campus-wide technology ecosystem. The role focuses on strategy, security, infrastructure, and administrative and academic computing, with partnership across schools and operations to advance the school’s mission.

The on-site, full-time position requires a track record of leading enterprise IT initiatives, strong executive communication, and a commitment to student-centered