IT Support Specialist

We are looking for a technically sharp, self-motivated IT Support Specialist to serve as the first point of contact for all internal IT helpdesk issues at GWII. This is not a typical ticket-queue role. We need someone who takes ownership, digs into problems, and comes with the tools and instincts to resolve issues efficiently. The right candidate will have a strong Tier 2/3 support background and will be actively developing their skills toward a Systems or Network Administrator role. This position reports to the Director of IT and operates in a hybrid work arrangement., Helpdesk & End-User Support

• Serve as the primary point of contact for all IT support requests submitted via Zendesk
• Triage, prioritize, and resolve Tier 1/2/3 incidents covering hardware, software, networking, and Microsoft 365
• Manage endpoint configuration, deployment, and troubleshooting via RMM tooling
• Maintain user support KB articles, to help allow users self service.
• Maintain accurate asset inventory and device records.
• Own end-user machine patch management, including scheduling, deployment, and compliance reporting across all managed endpoints via RMM tooling
• Provide clear, timely communication to end users throughout the lifecycle of their tickets
• Escalate issues to the Director of IT or appropriate vendor/specialist when resolution requires deeper expertise.
• Be available to respond to occasional after-hours and weekend IT issues, including system outages, critical incidents, and scheduled maintenance windows

Systems & Identity Administration

• Manage user lifecycle in Microsoft Entra ID including provisioning, deprovisioning, group membership, and conditional access policies
• Administer Microsoft 365 services including Exchange Online, SharePoint, Teams, and Intune
• Support endpoint management and compliance policy enforcement
• Assist with onboarding and offboarding workflows, ensuring access is granted and revoked accurately and on time
• Acquire, install, and test system and software upgrades and new computer hardware components, * Support and troubleshoot LAN/WAN connectivity issues across office and remote environments
• Assist with firewall rule management, VLAN configuration, and network access controls
• Work alongside the Director of IT on infrastructure projects including network upgrades and security hardening
• Monitor network health and respond to alerts from monitoring platforms

Scripting & Automation

• Write and maintain PowerShell scripts to automate repetitive IT tasks
• Identify manual processes that can be improved through automation and proactively propose solutions
• Maintain documentation of IT infrastructure, systems configurations, and troubleshooting procedures, including runbooks and self-service guides

• 5+ years of hands-on IT support experience, with demonstrated Tier 2/3 competency
• Proficiency with Microsoft Entra ID (formerly Azure AD) including user management, groups, and Conditional Access
• Experience administering M365 services (Exchange Online, Teams, SharePoint, Intune)
• Solid understanding of networking fundamentals: TCP/IP, DNS, DHCP, VLANs, and firewall concepts
• Hands-on experience with a RMM platform for endpoint management and remote support
• Working knowledge of PowerShell scripting for task automation and system administration
• Experience with a ticketing system such as Zendesk, Freshservice, or equivalent
• Strong hardware and software troubleshooting skills.
• Excellent written and verbal communication skills; able to explain technical issues clearly to non-technical users
• Self-starter mentality with the ability to manage competing priorities without constant direction
• Willingness and ability to be reached outside of normal business hours on an as-needed basis for urgent IT issues., * Experience managing or troubleshooting enterprise firewalls and network devices.
• Microsoft certifications (MS-102, AZ-104, SC-300, or equivalent)
• Familiarity with ITIL frameworks and change management processes
• Experience with Power Automate or other workflow automation platforms
• CompTIA Network+ or Security+ certification

Gulf Winds International, Inc. is a leading provider of drayage, transloading, and storage, serving importers and exporters globally. The Company prides itself on innovation, people, and purpose, redefining expectations for intermodal trucking. With a robust presence at major ports, including Houston, Dallas, Mobile, Memphis, Savannah, Charleston, Norfolk, Baltimore, and Chicago, Gulf Winds is dedicated to delivering top-notch services through continuous investment in technology and infrastructure. Ownership: The company is backed by The Sterling Group, a Houston-based private equity firm. Since 1982, The Sterling Group has partnered with management teams to grow and build winning businesses in the industrial sector. Over 75% of Sterling’s past partnerships have been with family businesses and corporate carve-outs. Sterling excels as a partner bringing its operational focus and expertise to support company objectives. Today, Sterling has over $5.7 billion in assets under management.