Tier 2 Support Analyst

Adastra; Chicago (IL); Hybrid; USD 55,000 - 75,000; Full time

Benefits offered by this job

Job summary

Adastra is seeking an IT Help Desk Analyst – Level II (Infrastructure Focus) to provide advanced support across end-user systems and core infrastructure in a hybrid environment centered in the Greater Chicago Area. You will escalate complex desktop, server, and network issues, assist with virtualization, AD, and SQL-related tasks, and help maintain system stability and security.

You’ll work across Windows/Mac users, Windows Server environments, VMware/Hyper-V/Azure, and collaborate with vendors

Qualifications

• 3–5+ years of IT support experience in Help Desk/Desktop/Infrastructure.
• Strong troubleshooting across servers, networking, and end-user systems.
• Hands-on with Windows Server 2016/2019/2022, Active Directory/Group Policy, and virtualization (VMware/Hyper‑V/Azure).
• Solid networking fundamentals (DNS, DHCP, TCP/IP, VPN).
• Experience with ticketing systems (ServiceNow, Jira, etc.).

Responsibilities

• Act as Tier 2 escalation point for complex desktop, application, and system issues, troubleshooting hardware, software, and OS-related problems across Windows/Mac environments, and supporting Microsoft 365, Active Directory, and user account administration
• Maintain and troubleshoot Windows Server environments (patching, performance, uptime), support file servers, print services, and domain services, and assist with system monitoring, alerts, and capacity management
• Administer and support virtual environments (VMware, Hyper‑V, or Azure VMs), including provisioning, configuration, monitoring, backups, snapshots, and disaster recovery processes
• Troubleshoot LAN/WAN, VPN, and connectivity issues, support switches, firewalls, and wireless infrastructure, and work with vendors/ISPs to resolve escalated network incidents
• Provide basic database administration support (SQL Server or similar), including backups, restores, performance troubleshooting, and supporting application teams with data-related issues, while also enforcing security policies, maintaining documentation, and identifying recurring issues for long-term fixes

Skills

IT support

Troubleshooting

Windows Server

Networking fundamentals

Ticketing systems

Tools

VMware

Hyper-V

Azure

Job description

IT Help Desk Analyst – Level II (Infrastructure Focus)

Location: Hybrid - Greater Chicago Area or Greenville, SC

Employment Type: Full Time | Direct Hire

Why You'll Love This Opportunity

Join a team looking for an IT Help Desk Analyst to provide advanced technical support across end-user systems and core infrastructure, including servers, virtual environments, networking, and databases. This role serves as an escalation point for Level I support and plays a key role in maintaining system stability, performance, and security across the organization.

What You'll Be Doing

• Act as Tier 2 escalation point for complex desktop, application, and system issues, troubleshooting hardware, software, and OS-related problems across Windows/Mac environments, and supporting Microsoft 365, Active Directory, and user account administration
• Maintain and troubleshoot Windows Server environments (patching, performance, uptime), support file servers, print services, and domain services, and assist with system monitoring, alerts, and capacity management
• Administer and support virtual environments (VMware, Hyper‑V, or Azure VMs), including provisioning, configuration, monitoring, backups, snapshots, and disaster recovery processes
• Troubleshoot LAN/WAN, VPN, and connectivity issues, support switches, firewalls, and wireless infrastructure, and work with vendors/ISPs to resolve escalated network incidents
• Provide basic database administration support (SQL Server or similar), including backups, restores, performance troubleshooting, and supporting application teams with data-related issues, while also enforcing security policies, maintaining documentation, and identifying recurring issues for long-term fixes

What We're Looking For

• 3–5+ years of IT support experience (Help Desk / Desktop / Infrastructure)
• Strong troubleshooting skills across servers, networking, and end-user systems
• Hands‑on experience with Windows Server (2016/2019/2022), Active Directory/Group Policy, and virtualization (VMware, Hyper‑V, or Azure)
• Solid networking fundamentals (DNS, DHCP, TCP/IP, VPN)
• Experience with ticketing systems (ServiceNow, Jira, etc.)

Why You'll Want This Role

This is a great opportunity for an IT professional who wants to move beyond basic help desk work and take on real ownership across servers, virtualization, networking, and databases. You'll serve as a key escalation point for the organization, work across a broad range of infrastructure, and have the chance to drive long-term fixes and process improvements rather than just closing tickets.