Tier 2 Support Analyst

Adastra; Chicago (IL); Hybrid; USD 65,000 - 85,000; Full time

Job summary

Adastra in Chicago is seeking an IT Help Desk Analyst to provide advanced technical support across end-user systems and core infrastructure, including servers, virtualization, networking, and databases. This role acts as an escalation point for Level I support and helps maintain system stability, performance, and security.

You will troubleshoot complex desktop, server, and network issues, support Windows/Mac, Active Directory, VMware/Hyper-V/Azure, DNS/DHCP, and ensure proper documentation and

Qualifications

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

Responsibilities

• Act as Tier 2 escalation point for complex desktop, application, and system issues.
• Maintain and troubleshoot Windows Server environments, patching, performance, and uptime.
• Administer and support virtual environments (VMware, Hyper-V, or Azure VMs).
• Troubleshoot LAN/WAN, VPN, and connectivity issues; support switches, firewalls, and wireless infra.
• Provide basic database administration support (SQL Server or similar) and enforce security policies.

Skills

Windows Server

Active Directory

Virtualization

Networking basics

Help desk tools

Tools

ServiceNow

Jira

Job description

Location: Hybrid - Northern Chicago Suburbs

Employment Type: Full Time | Direct Hire

Start Date: ASAP

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.