The iPrint Group is seeking an experienced, results-oriented System Administrator to lead the management, security, and optimization of our IT infrastructure, cloud environments, enterprise networks, and digital signage technology platforms across Jamaica.

This role is ideal for a technically strong professional who can manage complex IT environments, maintain critical business systems, and support the technology that powers one of Jamaica's leading printing, branding, and digital advertising organizations. The successful candidate will play a key role in ensuring the reliability, security, and scalability of our technology infrastructure while supporting the delivery of digital content to an island-wide network of digital advertising displays.

Key Responsibilities

IT Infrastructure & Systems Management

• Design, implement, administer, and maintain the organization's server infrastructure, including Windows Server environments, Active Directory, Group Policy, virtualization platforms, storage systems, and cloud-based services.
• Manage Microsoft 365 and/or Google Workspace environments, including user provisioning, security policies, email systems, collaboration platforms, and identity management.
• Monitor, optimize, and troubleshoot enterprise systems to ensure maximum uptime, reliability, scalability, and performance of business-critical applications and services.
• Plan and execute system upgrades, migrations, patch management, and infrastructure improvement projects to support business growth and technological advancement.

Digital Signage & OOH Technology

• Administer and support the technology infrastructure powering the company's island-wide Digital Out-of-Home (DOOH) advertising network, ensuring uninterrupted content delivery and system availability.
• Configure, monitor, troubleshoot, and maintain digital signage media players, LED display controllers, content management systems (CMS), and supporting hardware.
• Perform remote diagnostics and issue resolution for digital display assets located across multiple parishes, minimizing downtime and operational disruptions.
• Support the deployment, commissioning, integration, and ongoing maintenance of new digital signage installations and technology platforms.

Network Administration

• Design, implement, secure, and maintain enterprise LAN, WAN, VPN, wireless, and cloud networking environments across all company locations and remote sites.
• Configure and manage routers, switches, firewalls, VLANs, network segmentation, and access control policies to ensure security and operational efficiency.
• Monitor network performance, availability, and bandwidth utilization while proactively identifying and resolving bottlenecks and connectivity issues.
• Liaise with telecommunications providers, internet service providers, and technology vendors to maintain optimal connectivity and service delivery standards.

Cybersecurity, Business Continuity & Compliance

• Implement and enforce cybersecurity controls, endpoint protection solutions, vulnerability management programs, and security best practices across the organization.
• Conduct security assessments, system audits, risk reviews, and remediation activities to protect company and client data.
• Manage enterprise backup, disaster recovery, and business continuity processes, including regular testing and validation of recovery procedures.
• Ensure compliance with data protection requirements, information security policies, and applicable regulatory standards.

User Support & Technical Guidance

• Provide advanced technical support and troubleshooting assistance for infrastructure, network, and systems-related issues.
• Deliver technical guidance, training, and support to employees and stakeholders as required.

Technology Assets & Vendor Management

• Maintain oversight of IT assets, software licensing, subscriptions, and technology inventories.
• Evaluate, recommend, and coordinate technology purchases, upgrades, vendor services, and support agreements.

Qualifications & Experience

Required

• Bachelor's Degree in Information Technology, Computer Science, Information Systems, or a related discipline.
• Minimum of three (3) years' experience in Systems Administration, Infrastructure Administration, Network Administration, or a similar technical role.
• Strong hands-on experience with:
  • Windows Server (2016/2019/2022)
  • Active Directory and Group Policy Administration
  • Microsoft 365 Administration
  • TCP/IP Networking
  • VLANs, Routing, Switching, and Firewall Management
  • VPN Technologies
• Experience administering cloud environments such as Microsoft Azure, Amazon Web Services (AWS), or Google Cloud Platform (GCP).
• Experience with virtualization technologies including VMware and/or Hyper-V.
• Experience implementing and supporting backup and disaster recovery solutions such as Veeam, Acronis, or similar platforms.
• Strong troubleshooting and diagnostic skills across systems, networks, and infrastructure environments.

Core Competencies

• Advanced analytical and problem-solving capabilities.
• Strong understanding of enterprise IT infrastructure and cybersecurity principles.
• Excellent verbal and written communication skills.
• Ability to explain complex technical concepts to non-technical stakeholders.
• Strong project planning and execution skills.
• Ability to manage multiple priorities in a fast-paced environment.
• High level of integrity, professionalism, and discretion.
• Strong customer service orientation and commitment to operational excellence.
• Ability to travel to field locations across Jamaica when required.