Requirements
• Minimum 5 years of independent, hands-on experience in IT systems administration, application support/development, networking, and technical troubleshooting.
• Demonstrated experience building, configuring, administering, maintaining, and troubleshooting Windows and Linux/Ubuntu server environments, rather than end-user support alone.
• Strong practical experience with:
o Windows Server and Ubuntu/Linux administration
o Virtual machines and virtualized application environments
o Docker and containerized application environments
o TCP/IP networking, firewalls, access controls, and network security
o Windows/Linux workstations and server-to-client connectivity
o Grandstream PBX and IP telephone systems
• Experience with database and application development/integration, including:
o 4th Dimension (4D) database/application environments
o MySQL and SQL/database connectivity
o PHP, CSS, JavaScript and AJAX
o SOAP/API and system-to-system integrations
• Proven ability to troubleshoot across the application, database, operating system, network, firewall, and integration layers.
• Practical experience supporting healthcare technology, including CML Radiology Information Systems (RIS), PACS, OpenEMR, clinical workstations, and healthcare application workflows.
• Hands-on experience designing, configuring, testing, and troubleshooting local or self-hosted AI-agent environments, including workflow automation, Retrieval-Augmented Generation (RAG), structured knowledge retrieval, agent memory/context management, and integration of AI tools with existing software and IT workflows.
• Working knowledge of cybersecurity, including system access controls, user privileges, endpoint/server security, network defense, threat identification, and security-related troubleshooting.
• CompTIA A+ certification together with documented training in Windows Server administration, networking, cybersecurity, or equivalent relevant technical training.
• Ability to work independently, document technical changes, communicate effectively with users and vendors, and support systems within a confidential healthcare environment.
Key Responsibilities:
• Install, configure, administer, maintain, and troubleshoot company servers, workstations, networks, firewalls, software, databases, and communication systems.
• Maintain Windows and Linux server environments, virtual machines, Docker/container environments, access controls, system updates, and security configurations.
• Maintain and troubleshoot OpenEMR, RIS/PACS, healthcare applications, and related connectivity and workflows.
• Maintain and support 4D and MySQL database/application environments and associated web, API, and system integrations.
• Perform software development, scripting, application configuration, testing, debugging, deployment, and technical documentation as required.
• Configure and maintain network infrastructure, firewall rules, network-connected devices, Grandstream PBX, IP phones, and related communication systems.
• Develop, configure, test, integrate, and maintain local AI-agent and AI-assisted automation environments for approved technical and operational workflows.
• Investigate technical problems through hardware, operating system, network, security, database, application, and integration layers to identify root causes.
• Provide end-user technical support, implementation assistance, system training, and user guidance.
• Coordinate technical work with management, users, vendors, and external development resources and maintain appropriate system and change documentation.
This vacancy is listed on WORC, the Cayman Islands government job portal. Applications go through the official channel.
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