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REPORTS TO:   Director of Technology & Information Systems

SCHEDULE: 12-month appointment (renewable annually)

FUNCTION: Under the direction of the Director of Technology and guidance by the Associate Director of Infrastructure Operations, the Technology Support Specialist is the first level response to the Academy, providing support of classroom techniques (projectors, displays, digital whiteboards, etc.).


  • Help Desk 

    • Provide primary technology support for student and employees.

    • Review and assign technology requests submitted to help desk system.

    • Support academic technology requirements in the classroom environment.

    • Support end user system access for email and network services.

    • Close help desk requests and provide follow-up.

    • Maintain help desk system.

  • Network Maintenance 

    • Assist in maintaining the LAN and WAN. This includes resolving issues impacting network performance.

    • Install/Update network appliance hardware, software and configurations to insure best network performance.

    • Manage user, system and computer network accounts.

  • Server Management 

    • Perform/Maintain/Update backup services for network servers and data.

  • Digital Systems Management 

    • Perform/Manage system and application installation and updates for Academy owned digital systems.

    • Maintain digital systems and applications licensing and inventory.

    • Perform digital system imaging and deployment.

    • Support/Troubleshoot digital systems and applications performance.

  • Other duties as directed by the Director of Technology and Information Systems, the Associate Director of Infrastructure, or Chief Financial Officer.

Shared Office Responsibilities include:

  • Respond to major network outages and failures on a 7 x 24 basis. 

  • Manage technology related expectations with client and customer base. 

  • Maintain open lines of communication with all constituents to insure needs are met and issues are resolved in a timely manner.

  • Participate in ongoing professional development activities offered via CAIS and other outside entities.

  • Support academic technology requirements in the classroom environment.

  • Support end user system access for email and network services.

  • Telecommunications account management.


  • Bachelor’s Degree and three years of experience in a related field is required.

  • Experience working in a school setting is preferred.

Experience with the following technology is required:

  • Help Desk systems, Anti-Spam systems,

  • Microsoft Office 365, Windows, Azure, Active Directory,

  • G Suite for education, Virtual Machine Technology

  • Blackbaud: Raiser’s Edge NXT, Financial Edge NXT, Student Information System

  • Wifi Technologies and support, Computer Imaging and Deployment systems

  • Switching, Routing, Firewalls and other related technologies


  • Excellent interpersonal skills; ability to collaborate widely with various constituencies throughout the School’s community including students, faculty, staff, parents and trustee members.

  • Superior written and oral communication skills

  • Meticulous attention to detail; continually looks for ways to improve and promote quality and demonstrates accuracy and thoroughness.

  • Ability to prioritizes and plan work activities, uses time efficiently and develops realistic action plans; ability to multi-task and handle multiple projects, work quickly and with accuracy while maintaining composure and flexibility.

  • High-level troubleshooting skills and application of logic in order to solve complex problems.

Compensation and title will be commensurate with experience and qualifications. Offer will be contingent upon successful completion of a background check.

Interested applicants should send a letter of interest, resume, and three professional references to Kristin Welage, Director of Human Resources at


Organization: Cheshire Academy
Job Category:
Specialist / Associate
Areas of Responsibility:
Support / Help desk
Job Level:
Entry-level position
Job Sector:
Information Technology