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Employment Opportunities
at Pilot

The Pilot School is an incredible place to work. We are always looking for innovative, curious professionals who can bring energy and enthusiasm to whatever they do. With state-of-the-art facilities, a robust support team, a commitment to excellence, and a love of teamwork, Pilot faculty and staff have much longer than average career spans at the school. Our students benefit from the wisdom and experience of our teaching corps, and we constantly strive to push ourselves to new horizons. 

As an organization dedicated to unlocking the potential of each and every one of our students, The Pilot School recognizes the necessity for a diverse, inclusive, and equitable community. As such, the Pilot School is an equal opportunity employer and committed to being a workplace free of discrimination and harassment. Our employment decisions and personnel policies do not discriminate on the basis of race, color, national or ethnic origin, age, religion or religious creed, sexual orientation, gender identity and/or expression, disability or any other characteristic protected under applicable federal, state or local law.


At this time, The Pilot School is accepting applications for the following positions:

Director of Information Technology

Reports to: Head of School

Job Summary

The Pilot School is looking for a creative, curious, and collaborative leader to join its team.  The Director of Information Technology is responsible for the overall planning, organization, integration, implementation, and maintenance of all IT functions at the school.  As the school is at an exciting inflection point in its technology integration and programming, this position calls for a blend of technical expertise, innovative systems thinking, and collaborative leadership.  The ideal candidate will bring new ideas and initiatives to Pilot and be an integral part of their execution.

Essential Duties and Responsibilities

  • Technology Strategy and Initiative:Create and continue to nurture a strategic and long-range technology plan for the school that includes initiatives for improving IT infrastructure.
  • Infrastructure Management: Ensure the coordination, security, and efficiency of the IT infrastructure, including the network, hardware and devices, software, cloud platforms, firewall, databases, and servers.
  • Hardware and Software Management: Manage, install and maintain inventory of all hardware, including desktops, laptops, tablets, document cameras, projectors, network devices, printers, and other technology equipment.
  • Data Management and Security: Secure, back up, and consolidate data systems and information; Collaborate with the Business Manager to ensure compliance with all information security requirements.
  • Technical Support and Troubleshooting: Assess and respond to IT needs as voiced by faculty, administration, and staff.
  • User Training and  Professional Development: Train users in all aspects of technology usage across campus; Plan and supervise internal and external training of the school’s staff.
  • IT Budget Management: Develop and manage the school’s computer/device operating and IT budget.
  • Collaboration and Communication: Serve on the school’s leadership team, specifically working to problem solve and contribute to the execution of the school’s mission and vision.  
  • Policy Development: Develop documentation, policies, and procedures for all technology usage
  • Growth and Innovation: Identify, evaluate, and recommend new and emerging technologies for classroom and administrative uses; Remain current on new developments in the areas of software, hardware, networks, telecommunications, training, and maintenance; Continue to position the school advantageously as it grows its technology capacities
  • General Administration: Manage user accounts across multiple platforms, Manage vendor relations, procurement, installation, and implementation of information systems

Qualification Requirements

  • A bachelor’s degree or equivalent job experience
  • Strong knowledge of Mac OS and Chrome OS
  • Experience with network management platforms and network security
  • Experience maintaining and configuring student information systems
  • Experience with Google Workspace
  • Experience training users of various skill levels, cultivating others’ confidence with technology through a positive attitude
  • Curiosity, passion for technology, and a problem solving mindset
  • Well developed organization and self-directed project management skills
  • Five years’ previous work experience in the IT field
  • Capability to lift up to 25 pounds and access hardware in hard-to-reach spaces

Please submit your cover letter with resume to



  • Bachelor’s Degree in Elementary Education required.
  • Teaching experience in an early childhood or elementary classroom.
  • Must have excellent communication skills, and a deep commitment to children with learning differences.
  • Current clearances or willingness to obtain clearances including State of Delaware Criminal Background clearance and DE Child Abuse clearance.

Please submit your cover letter with resume to

The Pilot School provides equal opportunity to all otherwise qualified applicants/students and does not discriminate on the basis of race, color/religion or creed, sex, sexual orientation, gender identity, national origin, disability, or other protected status, The school will make reasonable accommodation(s) of a disability so long as the accommodations do not present an undue hardship to the school.

Don’t see a position that’s right for you?

If there is not a position listed that’s right for you but you’d like us to keep your resume on file, send your materials to, or contact us if you have any questions. We look forward to speaking with you!