Microsoft Systems Engineer: Windows Server & Cloud

drweng; Chicago (IL); On-site; USD 120,000 - 160,000; Full time

Benefits offered by this job

Medical Insurance

Dental & Vision Insurance

401k with discretionary employer match

Short/Long-term Disability

Life & AD&D Insurance

HSA/FSA

Job summary

DRW, a Chicago-based trading firm, seeks an IT Systems Administrator to manage Windows Server infrastructure across on-prem, cloud, and hybrid environments. You will configure AD, DNS/DHCP, GPO, Exchange, and cloud services while supporting SSO, federation, and security automation.

Strong scripting skills (PowerShell, Python) and experience with monitoring tools are desirable. Expect on-call rotations and weekend maintenance as part of a global team supporting critical production systems.

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 (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.
• Eager to learn, collaborate, and find solutions under 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

Windows Server

Active Directory

DNS

DHCP

Group Policy

SCCM/MECM

PowerShell

Python

Entra ID

Exchange (Server/Online/Hybrid)

Networking fundamentals

VM deployments

Tools

Splunk

Grafana

Alertmanager

Prometheus

DevOps/CI CD

IaC

Kubernetes

Job description

DRW, a Chicago-based trading firm, seeks an IT Systems Administrator to manage Windows Server infrastructure across on-prem, cloud, and hybrid environments. You will configure AD, DNS/DHCP, GPO, Exchange, and cloud services while supporting SSO, federation, and security automation.

Strong scripting skills (PowerShell, Python) and experience with monitoring tools are desirable. Expect on-call rotations and weekend maintenance as part of a global team supporting critical production systems.