IT Manager - work in the Cayman Islands! TAX FREE!
IT Manager - work in the Cayman Islands! TAX FREE!

IT Manager - work in the Cayman Islands! TAX FREE!

Milton Full-Time 43200 - 72000 £ / year (est.) No home office possible
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At a Glance

  • Tasks: Lead IT operations in a hands-on role, ensuring performance and security of systems.
  • Company: Join a well-established retail employer in the sunny Cayman Islands.
  • Benefits: Enjoy a competitive, TAX FREE salary, relocation assistance, and various perks.
  • Why this job: Experience island life while making a real impact in IT management.
  • Qualifications: 10+ years in IT management with relevant certifications like Microsoft, Cisco, and VMware.
  • Other info: Relocation support provided; ideal for adaptable candidates ready for an adventure.

The predicted salary is between 43200 - 72000 £ per year.

Here’s a unique opportunity to take on a hands-on IT leadership role with a well-established retail employer in the sunny, TAX FREE Cayman Islands! On behalf of our retail-focused client in Grand Cayman, we are seeking a motivated IT professional with relevant industry certifications across Microsoft, Cisco, VMware and more, who can bring verifiable expertise to the company’s IT function.

Reporting to the organization’s CFO, and acting in a fully hands-on capacity as the primary internal IT resource, the IT Manager will be responsible for the overall performance, security and resiliency of all hardware, software and networks utilized by a retail-focused business (and possibly one or more related companies), including the management of:

  • Windows Server 2016/2022, Hyper-converged infrastructure, HPE Servers, VMware ESXi 8 and vSphere clusters
  • Microsoft SCCM/SCOM, RemoteApp, Exchange, Microsoft 365, Endpoint protection, Citrix Metaframe, Veeam Backup & Replication, VMware Site Recovery Manager, SQL Server, Retail management and Point-of-Sale systems, timekeeping and Accounting applications
  • Business Continuity/Disaster Recovery, Hyper-converged virtual SANs, site-to-site replication to DR site
  • Next-Gen Palo Alto firewall cluster, HP/Cisco switches, wireless access points
  • Fiber and DSL connections, VPN, Mitel UC telephony
  • Retail Point-of-sale stations, desktop workstations, virtual sales POS systems
  • Biometric timekeeping devices, Multi-function IP printers
  • Building Management Systems including Fire alarm, security system, lighting controls, IP CCTV systems
  • Coordinating the work of third party MSP / IT service providers

Requirements:

  • At least 10 years of current, hands-on IT management and systems administration experience covering (as much as possible of) the technologies in place as listed above.
  • Relevant industry certifications are required. At minimum, our client is looking for current certification in the core technologies upon which the businesses rely including:
  • Microsoft certifications: Microsoft 365, Windows Server, Exchange, MCSE Core Infrastructure 2016, Windows 10/11
  • Cisco CCNP
  • VMware VCP 2023
  • ITIL
  • CISSP or similar preferred - or willingness to pursue (employer supported)
  • Due to the international move required, we are targeting a highly adaptable candidate who is able to relocate easily with few complications.
  • Our client offers a competitive, TAX FREE compensation package. Relevant work permit application, relocation cost assistance and a range of benefits will be offered. If you have the above certifications and experience, and have the ability to make a move like this, please apply and/or contact Jason Squires for an introductory conversation.

    IT Manager - work in the Cayman Islands! TAX FREE! employer: Squires Partners Inc.

    Join a dynamic retail employer in the stunning, TAX FREE Cayman Islands, where you will thrive in a supportive work culture that values innovation and collaboration. As an IT Manager, you will benefit from competitive compensation, comprehensive relocation assistance, and opportunities for professional growth, all while enjoying the unique lifestyle and vibrant community that Grand Cayman has to offer.
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    Contact Detail:

    Squires Partners Inc. Recruiting Team

    StudySmarter Expert Advice 🤫

    We think this is how you could land IT Manager - work in the Cayman Islands! TAX FREE!

    ✨Tip Number 1

    Make sure to highlight your hands-on experience with the specific technologies mentioned in the job description. Tailor your discussions to showcase your expertise in areas like Windows Server, VMware, and Microsoft 365 during any networking opportunities or interviews.

    ✨Tip Number 2

    Research the company and its IT infrastructure thoroughly. Understanding their current systems and challenges will allow you to ask insightful questions and demonstrate your genuine interest in the role during conversations with recruiters or hiring managers.

    ✨Tip Number 3

    Network with professionals already working in the Cayman Islands or in similar roles. They can provide valuable insights into the local job market and may even refer you to opportunities within their organisations.

    ✨Tip Number 4

    Be prepared to discuss your adaptability and willingness to relocate. Highlight any previous experiences where you successfully managed transitions or changes, as this will reassure employers of your capability to handle the move to the Cayman Islands.

    We think you need these skills to ace IT Manager - work in the Cayman Islands! TAX FREE!

    Hands-on IT Management
    Systems Administration
    Microsoft 365
    Windows Server 2016/2022
    VMware ESXi 8
    Hyper-converged Infrastructure
    Cisco Networking (CCNP)
    Microsoft Exchange
    SQL Server Management
    Business Continuity Planning
    Disaster Recovery Solutions
    ITIL Framework
    CISSP or willingness to pursue
    Remote Desktop Services
    Point-of-Sale Systems Management
    Network Security (Palo Alto Firewalls)
    VPN Configuration
    Telephony Systems Management (Mitel UC)
    Third-party Vendor Coordination
    Adaptability for Relocation
    Excellent Communication Skills

    Some tips for your application 🫡

    Tailor Your CV: Make sure your CV highlights your relevant IT management experience and certifications. Focus on the technologies mentioned in the job description, such as Microsoft, Cisco, and VMware, to demonstrate your expertise.

    Craft a Compelling Cover Letter: Write a cover letter that showcases your passion for the role and the unique opportunity of working in the Cayman Islands. Mention your adaptability and willingness to relocate, as well as how your skills align with the company's needs.

    Highlight Certifications: Clearly list your industry certifications in your application. Ensure you include all relevant qualifications, especially those specifically requested, like Microsoft 365, CCNP, and VCP 2023, to stand out to the employer.

    Showcase Leadership Experience: In your application, emphasise any previous leadership roles or projects where you managed IT teams or systems. This will demonstrate your capability to take on a hands-on IT leadership role as described in the job posting.

    How to prepare for a job interview at Squires Partners Inc.

    ✨Showcase Your Technical Expertise

    Make sure to highlight your hands-on experience with the specific technologies mentioned in the job description, such as Windows Server, VMware, and Cisco. Be prepared to discuss real-world scenarios where you've successfully implemented or managed these systems.

    ✨Demonstrate Leadership Skills

    As an IT Manager, you'll be leading a team and coordinating with third-party service providers. Share examples of how you've effectively led teams, resolved conflicts, and ensured smooth operations in previous roles.

    ✨Prepare for Scenario-Based Questions

    Expect questions that assess your problem-solving abilities in real-time situations. Prepare to discuss how you would handle potential IT crises, such as system failures or security breaches, and outline your approach to business continuity and disaster recovery.

    ✨Express Adaptability and Willingness to Relocate

    Since this role involves relocating to the Cayman Islands, convey your enthusiasm for the move and your adaptability to new environments. Discuss any previous experiences you have had with relocation or working in diverse settings.

    IT Manager - work in the Cayman Islands! TAX FREE!
    Squires Partners Inc.
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    • IT Manager - work in the Cayman Islands! TAX FREE!

      Milton
      Full-Time
      43200 - 72000 £ / year (est.)

      Application deadline: 2027-05-23

    • S

      Squires Partners Inc.

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