Senior Director, Information Technology

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

Job Description - Senior Director, Information Technology (26000194)

Senior Director, Information Technology - ( 26000194 )

Description

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 schoolwide 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 talent‑development skills, with a demonstrated ability to build, mentor, and lead high‑performing, collaborative, and accountable teams.
• Strong financial, operational, and portfolio management skills, including budgeting, procurement, contract negotiation, vendor management, technology lifecycle planning, and prioritization of competing investments and initiatives.
• Excellent communication, collaboration, and executive presence, with the ability to build trusted relationships and translate complex technology opportunities, risks, and issues into clear recommendations for senior leaders and non‑technical stakeholders.
• Strong customer and service orientation, with demonstrated success establishing service standards, performance expectations, accountability, and technology solutions that improve the user experience and organizational effectiveness.
• Ability to evaluate emerging technologies and industry trends for strategic value, organizational fit, cybersecurity and operational risk, sustainability, and long‑term business value.
• Experience supporting a complex educational or similarly multifaceted organization preferred, with an understanding of academic, student, administrative, and business technology needs.
• High degree of integrity, sound judgment, and commitment to the MHS mission, including a genuine enthusiasm for engaging with students and serving as a positive role model.

At MHS, technology is more than infrastructure and systems. It connects the people, programs, and experiences that help students thrive. The Senior Director, Information Technology will have the opportunity to shape the future of technology at MHS while strengthening teaching and learning, improving operational effectiveness, protecting critical systems and information, and helping advance a mission that has transformed the lives of students for more than a century.

Schedule

Full-time

Job Type

Standard

Job Posting

Oct 28, 2026

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Milton Hershey School does not discriminate in admissions or other programs and services on the basis of race, color, national or ethnic origin, ancestry, sex, religious creed or disability. Read on equal opportunity and diversity, equal employment opportunity, and more. important MHS policies

Milton Hershey School does not discriminate in admissions or other programs and services on the basis of race, color, national or ethnic origin, ancestry, sex, religious creed or disability. . Equal Opportunity Policy