Systems Administrator (Tier 2 Support) (Chicago)

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What the job looks like

- Take the escalations Tier 1 can't close and fix them for good

- Administer Microsoft 365 and Entra ID: users, licenses, groups, MFA, conditional access

- Manage laptops and phones in Intune: enrollment, patching, compliance

- Maintain Active Directory and Group Policy, plus Windows Server where it still runs

- Run onboarding and offboarding, so access is granted and removed on time

- Write PowerShell to wipe out the tickets that keep coming back

- Document fixes so Tier 1 can handle the next one

What I'm looking for

- 3+ years in IT support, with time at Tier 2 or in a sysadmin role

- Hands-on Microsoft 365 admin: Exchange Online, Teams, SharePoint, Entra ID

- Intune or another MDM, plus Active Directory

- PowerShell you've used to fix a real problem

- Tickets and documentation other people can follow

- Based in the Chicago area

Nice to have

- Security+, MD-102 or MS-102

- Experience in financial services or another regulated environment

- Okta or another identity provider

The details

- Pay: $70K to $90K base. The final number depends on the employer and scope

- Location: Chicago area. The work model depends on the employer, from mostly remote to a few days onsite

- Type: direct hire