What are the responsibilities and job description for the Level 2 Tech position at Cii?
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 Responsibilities
- Manage and maintain on-site servers, networking equipment, switches, and cabling infrastructure across headquarters and remote branch locations
- Provide Level 2 escalation support for help desk tickets, resolving issues beyond the scope of Level 1
- Monitor system performance, conduct proactive maintenance, and implement patches and updates
- Support and troubleshoot transportation management systems (TMS), document imaging platforms, fuel management systems, and fleet telematics
- Administer Active Directory, Group Policy, Microsoft 365, and user account management
- Manage Hyper-V virtual machines and host infrastructure
- Manage backups, disaster recovery planning, and business continuity procedures
- Coordinate with the MSP partner on escalations, project work, and infrastructure changes
- Coordinate with carriers, vendors, and third-party logistics technology providers
- Support remote site connectivity including site-to-site VPNs and branch office networking
- Document configurations, procedures, and incident resolutions clearly and thoroughly
- Assist in planning and executing hardware refreshes, software rollouts, and infrastructure upgrades
- Communicate system status, outages, and technical decisions to non-technical staff and management in plain, understandable language
Required Qualifications
- 3 years in an IT support or systems administration role
- Demonstrated experience with on-site server administration (Windows Server)
- Hands-on experience with Hyper-V virtualization
- Microsoft 365 and Entra ID (Azure AD) administration
- Solid networking fundamentals: TCP/IP, VLANs, VPNs, DNS, DHCP
- Level 1/2 help desk experience with a ticketing system
- Experience in trucking, transportation, or logistics industry
- Basic working knowledge of McLeod LoadMaster or similar transportation management systems
- Ability to explain technical issues and solutions in plain language to non-technical stakeholders
- Strong troubleshooting, problem-solving, and follow-through skills
- Clear written and verbal communication, including thorough documentation habits
- Ability to lift and rack equipment; comfort working in a data closet or server room environment
Nice to Have
- CompTIA A , Network , or Security certification
- Microsoft certifications (MD-102, AZ-900, or higher)
- Experience with pfSense, Ubiquiti UniFi, or similar SMB networking platforms
- Familiarity with Transflo, FuelMaster, or similar transportation document imaging and fuel management systems
- Experience with ELD (Electronic Logging Device) systems or fleet camera platforms
- Azure cloud administration (virtual machines, virtual networking, VPN gateways)
- Scripting skills in PowerShell
- Experience supporting multi-site environments with remote branch offices
- Experience working in a co-managed IT model alongside an MSP
- Familiarity with backup platforms such as Acronis or Veeam
- Experience supporting warehouse or yard management systems