Senior Director, Information Technology

Lead technology that helps students thrive.

Milton Hershey School (MHS) is one of the world’s premier pre-K through 12th grade private schools, providing approximately 2,200 students from disadvantaged backgrounds with a cost-free home, exceptional education, and opportunities that prepare them for fulfilling and productive lives. Fully endowed through the generosity of Milton and Catherine Hershey, MHS has the resources and vision to continue expanding its impact.

MHS is seeking an accomplished, forward-thinking Senior Director, Information Technology to lead technology strategies and operations across our complex residential school environment. This highly visible leadership role will shape an integrated, secure, sustainable, and responsive technology ecosystem supporting students, educators, and administrative operations. The Senior Director will collaborate with other IT and School leaders to set technology strategy and priorities, anticipate emerging opportunities and risks, strengthen service delivery, and ensure technology investments advance the MHS mission.

This is a full-time, year-round, on-site position in Hershey, PA, with a compensation range of $173,100 to $231,088, based on experience, plus an excellent benefits package.

Key Responsibilities:

Develop and execute a multi-year IT strategy and technology roadmap aligned with School priorities, goals, and future technology needs.

Provide strategic and operational leadership for information technology operations and services, including infrastructure, applications, academic and administrative computing, cybersecurity, and end user support.

Lead, develop, and mentor IT management and staff, fostering accountability, collaboration, professional growth, strong performance, and a customer-focused culture.

Establish school wide technology governance, priorities, standards, policies, and long-range plans that guide technology investments, initiatives, architecture, and operational practices.

Lead major technology initiatives, modernization efforts, and system implementations with accountability for scope, timelines, budgets, organizational change, implementation, and measurable results.

Drive greater integration, efficiency, reliability, sustainability, and value from technology investments through effective architecture, lifecycle planning, standardization, and continuous improvement.

Enhance customer and user experience by establishing service levels, performance measures, responsive support practices, and strong partnerships with academic, administrative, and operating departments.

Provide effective financial and operational stewardship of technology resources through sound budgeting, procurement, technology lifecycle planning, contract and licensing management, vendor management, and investment planning.

Evaluate emerging technologies, including artificial intelligence and automation, along with cybersecurity considerations and industry trends, and translate them into responsible, practical opportunities for MHS.

Serve as a senior technology advisor to executive leadership, translating complex technology opportunities, risks, costs, and operational considerations into clear recommendations that support institutional decision-making.

Co-Chair the School’s Technology Steering Committee and strengthen technology governance across MHS, building partnerships with academic, administrative, and business leaders to establish priorities and improve institutional effectiveness.

Qualifications:

Bachelor’s degree in information technology, computer science, business, or a related field required; master’s degree preferred.

10+ years of progressively responsible technology leadership experience, including demonstrated success leading complex IT operations, teams, and enterprise technology initiatives in a large organization.

Broad expertise across enterprise technology, including infrastructure, networking, telecommunications, enterprise applications, data management, end-user computing, cybersecurity, risk management, and IT governance.

Demonstrated ability to develop and execute technology strategy and multi-year roadmaps that align technology priorities, investments, and resources with institutional goals.

Proven success leading major technology initiatives, system implementations, integrations, digital transformation, and organizational change, including the responsible adoption of emerging technologies such as artificial intelligence and automation.

Strong leadership and…