System Administrator Level 2.5 (MSP) (Palatine)

We are an MSP supporting small and mid sized businesses across the Chicagoland area. Our team offers the pace and variety of a local MSP with the support and structure of a larger organization. We value ownership, consistency, and continuous learning, and we are looking for a System Administrator with MSP experience who wants to grow while taking on meaningful technical responsibility.

This role is a strong fit for a mid level MSP engineer who can handle escalations, keep server environments healthy, and contribute to Microsoft 365 and Azure projects. You will work across multiple client networks, support cloud migrations, and partner with senior engineers on upgrades and modernization work.

Responsibilities

Take ownership of escalations across Windows Server, Microsoft 365, Azure, and core networking

Administer Windows Server 2016 to 2022 including Active Directory and Group Policy

Support Microsoft 365 migrations and improvements including Exchange Online and OneDrive

Work with Azure services including Entra ID, Intune, and Azure Virtual Desktop

Troubleshoot DNS, DHCP, VPN connectivity, VLANs, and firewall related issues

Assist with infrastructure upgrades, refreshes, and cloud transition projects

Maintain clean documentation and ticket updates in PSA and RMM tools

Travel to client sites as needed for deployments, maintenance, and higher touch support

Qualifications

3 to 5 years of MSP experience supporting multiple client environments

Strong skills in Microsoft 365, Azure, and Windows Server 2016 to 2022

Solid networking fundamentals including DNS, DHCP, VLANs, VPNs, and firewalls

Experience supporting Entra ID, Intune, and Azure Virtual Desktop

Comfortable handling escalations and participating in project work

Familiarity with Autotask and Kaseya or similar MSP toolsets

Strong communication, documentation, and problem solving skills

Certifications like Network+ or Microsoft 365 or Azure are a plus

Location, Pay, and Benefits

Chicagoland area role with client site visits as needed

Hybrid schedule after onboarding, 2 to 3 days work from home

Salary up to $90K plus monthly performance bonus

Health, dental, and vision insurance

Mileage reimbursement for client visits

Training and certification reimbursement

Supportive MSP culture with clear growth path