Microsoft Systems Engineer: Cloud/On-Prem Automation

DRW Holdings, LLC.; Chicago (IL); On-site; USD 120,000 - 160,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

401k with discretionary employer match

Disability insurance (short/long-term)

Life and AD&D insurance

Health Savings Account

Job summary

DRW is seeking an experienced Windows Server Administrator in Chicago to manage core Microsoft services, deploy and support Windows Server environments (2016–2025), and oversee cloud services Entra ID, OneDrive, and Microsoft 365. You will configure SSO/federation and triage critical production incidents.

Join a global on-call rotation, maintain runbooks, and collaborate across teams. The role emphasizes automation, scripting in PowerShell and Python, and a proactive approach to changes in a

Qualifications

• Experience managing Windows Server infrastructure in high visibility, mission critical environments.
• Experience administering Windows Server services: Active Directory, Group Policy, DNS, DHCP, Failover Clustering.
• Experience with Entra ID, Exchange (Server/Online/Hybrid) and MECM (SCCM) is preferred.
• You can use scripts (e.g. PowerShell, Python) to automate routine administrative tasks.
• Knowledge of networking fundamentals, server hardware and VM deployments.
• Strong written and verbal communication skills. You can work across teams and have evidence-based discussions on technical and operational topics.
• You are eager to learn, collaborate, and find solutions under interesting constraints.

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 services).
• 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

Active Directory

DNS

DHCP

Group Policy

Exchange

PowerShell

Python

Scripting

Entra ID

MECM/SCCM

Networking fundamentals

VM deployments

Documentation

On-call support

Tools

Splunk

Grafana

Alertmanager

Prometheus

DevOps / CI/CD

IaC

Kubernetes

Job description

DRW is seeking an experienced Windows Server Administrator in Chicago to manage core Microsoft services, deploy and support Windows Server environments (2016–2025), and oversee cloud services Entra ID, OneDrive, and Microsoft 365. You will configure SSO/federation and triage critical production incidents.

Join a global on-call rotation, maintain runbooks, and collaborate across teams. The role emphasizes automation, scripting in PowerShell and Python, and a proactive approach to changes in a