IT Systems Manager

Date Posted: Thursday 03 November 2022

Vacancy Type: Full-Time

Closing date for application: 25/11/2022 11:59pm

Cayman Prep and High School is a private, co-educational Christian school with over 1,000 students ranging from Kindergarten to Year 13 and offers a British-based international curriculum leading to IGCSE / GCSE and A-level qualifications. The school is renowned for providing a stimulating learning environment in which our students become critical, creative thinkers, responsible citizens and lifelong learners. This is evident in our consistent record of outstanding academic achievements, pastoral care and wide range of extra-curricular activities.


The school is currently seeking fully qualified and suitably experienced individuals to join our high performing School team in April 2023 or August 2023 for the following position:


IT Systems Manager


Duties will include, but will not be limited to:

  • Leading the strategic development of IT within the whole school, ensuring technology within the classroom to support teaching and learning.
  • Maintaining the School’s IT network infrastructure including switches, routing, firewalls, web-filtering and WiFi.
  • Install new and rebuild existing servers and configure hardware, peripherals, services, setting, directories, storage etc. in accordance with standards and operational requirements.
  • Managing the extensive range of IT software and hardware throughout the school.
  • Perform daily system monitoring and daily backup operations, ensuring all required file systems and data are successfully backed-up.
  • Applying patches and upgrades on a regular basis and upgrading administrative tools and utilities.
  • Troubleshooting and fault fixing.
  • Developing and managing the annual IT budget, as well as a 3 to 5 year rolling IT budget for hardware and software.
  • Managing and controlling an asset register of all IT equipment.
  • Developing and maintaining technology policies, procedural manuals, and checklists; including compliance with the Cayman Islands Data Protection Law, would be an asset.
  • Developing and maintaining the schools web page and design.
  • Liaising, where necessary, with external service providers and managing service contracts.
  • Management of in-house fault ticketing system.
  • Supervision of IT Technician.
  • Working alongside the Data and SIMS Manager to assist with any infrastructure requirements for effective running of the school information management system.
  • All staff will be expected to fully adhere to and support the Christian ethos of the school.


Qualifications, experience and skills required:

  • A first degree in Information Technology or Computer Science.
  • A minimum of 4 to 5 years’ experience as an IT Systems Manager, in an educational setting.
  • Strong leadership skills to lead the strategic development and management of a busy IT Department.
  • Experience in developing and delivering in-house IT training.
  • Must have the ability to troubleshoot and fix user problems with hardware and software.
  • Experience with SIMS, Microsoft server 2019 environments including SQL Servers, Active Directory, File / Print Servers.
  • Strong understanding of and experience with Hyper-V Server Virtualization Clusters with Dell or HP Storage SAN.
  • Knowledgeable in Joomla and WordPress web site design and maintenance.
  • Experience with Azure Virtual Machines Infrastructure.
  • Experience with managing Office 365 environments including Exchange, MS Teams, SharePoint, OneDrive, and User Management.
  • Experience utilizing Microsoft Endpoint Manager for device imaging, security policy distribution, and maintenance of device health for student and staff devices.
  • Experience with image management in an environment with diverse hardware and software requirements.
  • Strong background in designing backup and disaster recovery plans utilizing Veeam.
  • Experience with CISCO network switches and firewall configurations.
  • Must have the ability to work independently and efficiently to successfully manage multiple priorities.
  • Excellent organisational and interpersonal skills to work with a range of end users within a busy environment.


  • Essential Qualification Requirements

Office 365 – Microsoft 365 Certified: Enterprise Administrator Expert

Microsoft Servers – (MCSE) Microsoft Certificate Server Engineer

CISCO – Cisco Certified Network Associate (CCNA) Certification


  • Desirable Qualification Requirements

Teams – Microsoft 365 Certified: Teams Administrator Associate

Endpoint Manager – Exam MD-101: Managing Modern Desktops


Cayman Prep and High School is totally committed to safeguarding the welfare of our children and young people and expects the same commitment from all our employees. All successful candidates will be subject to enhanced pre-employment clearance including identity checks, criminal background checks, qualification checks and employment checks to include an exploration of any gaps in employment and three satisfactory employment checks.


Salary range for the IT Systems Manager is CI$ 56,000 – CI$ 76,000 per annum commensurate with experience. Benefits include:

  • Generous medical insurance
  • Contribution to a pension plan
  • Exceptional monetary relocation allowance on arrival
  • Return airfare
  • Tax free salary
  • Discounted school fees for 2 dependent children
  • Continued Professional Development Opportunities throughout the School Year.


For the position listed above applications will only be considered if submitted on the school’s relevant application form (available on the school website: and forwarded along with a covering letter and CV to:

Business Manager

Cayman Prep and High School

PO Box 10013

Grand Cayman KY1-1001



Deadline for receipt of applications: Friday, November 18th, 2022

Only short-listed candidates will be contacted


Supporting Documents