Microsoft Systems Engineer: Cloud & On-Prem Windows Infra

Precision Labs; Chicago, Northern (IL, KY); Hybrid; USD 120,000 - 160,000; Full time

Job summary

DRW, a diversified trading firm based in Chicago, seeks a Windows Server Administrator to manage core Microsoft services and hybrid Exchange environments.

You will deploy and maintain Windows Server ecosystems (2016–2025), configure SSO/federation (SAML, OAuth/OIDC, SCIM), and support Entra ID and Microsoft 365. Join a global on-call rotation with occasional weekend maintenance.

Strong scripting skills (PowerShell, Python) and experience in mission-critical environments are required.

Qualifications

• Experience managing Windows Server infrastructure in high-visibility environments.
• Experience administering AD, DNS, DHCP, Group Policy, and Failover Clustering.
• Experience with Entra ID, Exchange (Server/Online/Hybrid) and MECM (SCCM) preferred.
• Scripting ability (PowerShell or Python) to automate routine admin tasks.
• Strong written and verbal communication and cross-team collaboration.

Responsibilities

• Administer core Microsoft services: Active Directory, DNS, DHCP, Group Policy, Exchange (on-premise, Online, hybrid).
• Deploy, maintain and support Windows Server environments (2016-2025).
• Support Microsoft cloud services (Entra ID, OneDrive, Copilot, Microsoft 365).
• Configure single sign on and federation (SAML, OAuth/OIDC, SCIM).
• Triage and resolve tickets from the operations queue; respond to critical production incidents.
• Implement planned and ad hoc changes in accordance with firmwide change management processes.
• Maintain clear system documentation and capture specialized configurations as repeatable runbooks.
• Participate in a global support team with on call rotation and occasional weekend maintenance.

Skills

Windows Server administration

PowerShell scripting

Python scripting

Networking fundamentals

Strong communication

Tools

Entra ID

Exchange (Server/Online/Hybrid)

MECM (SCCM)

Job description

DRW, a diversified trading firm based in Chicago, seeks a Windows Server Administrator to manage core Microsoft services and hybrid Exchange environments.

You will deploy and maintain Windows Server ecosystems (2016–2025), configure SSO/federation (SAML, OAuth/OIDC, SCIM), and support Entra ID and Microsoft 365. Join a global on-call rotation with occasional weekend maintenance.

Strong scripting skills (PowerShell, Python) and experience in mission-critical environments are required.