Level 2 Tech

We are looking for a motivated and experienced Level 2 IT Technician / Systems Administrator to join our team. In this hands-on role, you will own the day-to-day health of our on-site infrastructure across multiple locations, serve as a key escalation point for help desk operations, and bring specialized knowledge of the unique technology demands found in trucking and transportation environments. You will work alongside our managed service provider (MSP) partner in a co-managed IT model, coordinating on projects, escalations, and infrastructure initiatives. If you thrive in a fast-moving, operationally critical setting where uptime truly matters, we want to hear from you.Key ResponsibilitiesManage and maintain on-site servers, networking equipment, switches, and cabling infrastructure across headquarters and remote branch locationsProvide Level 2 escalation support for help desk tickets, resolving issues beyond the scope of Level 1Monitor system performance, conduct proactive maintenance, and implement patches and updatesSupport and troubleshoot transportation management systems (TMS), document imaging platforms, fuel management systems, and fleet telematicsAdminister Active Directory, Group Policy, Microsoft 365, and user account managementManage Hyper-V virtual machines and host infrastructureManage backups, disaster recovery planning, and business continuity proceduresCoordinate with the MSP partner on escalations, project work, and infrastructure changesCoordinate with carriers, vendors, and third-party logistics technology providersSupport remote site connectivity including site-to-site VPNs and branch office networkingDocument configurations, procedures, and incident resolutions clearly and thoroughlyAssist in planning and executing hardware refreshes, software rollouts, and infrastructure upgradesCommunicate system status, outages, and technical decisions to non-technical staff and management in plain, understandable languageRequired Qualifications3+ years in an IT support or systems administration roleDemonstrated experience with on-site server administration (Windows Server)Hands-on experience with Hyper-V virtualizationMicrosoft 365 and Entra ID (Azure AD) administrationSolid networking fundamentals: TCP/IP, VLANs, VPNs, DNS, DHCPLevel 1/2 help desk experience with a ticketing systemExperience in trucking, transportation, or logistics industryBasic working knowledge of McLeod LoadMaster or similar transportation management systemsAbility to explain technical issues and solutions in plain language to non-technical stakeholdersStrong troubleshooting, problem-solving, and follow-through skillsClear written and verbal communication, including thorough documentation habitsAbility to lift and rack equipment; comfort working in a data closet or server room environmentNice to HaveCompTIA A+, Network+, or Security+ certificationMicrosoft certifications (MD-102, AZ-900, or higher)Experience with pfSense, Ubiquiti UniFi, or similar SMB networking platformsFamiliarity with Transflo, FuelMaster, or similar transportation document imaging and fuel management systemsExperience with ELD (Electronic Logging Device) systems or fleet camera platformsAzure cloud administration (virtual machines, virtual networking, VPN gateways)Scripting skills in PowerShellExperience supporting multi-site environments with remote branch officesExperience working in a co-managed IT model alongside an MSPFamiliarity with backup platforms such as Acronis or VeeamExperience supporting warehouse or yard management systems