Senior Windows Systems Engineer — AD, Entra ID & Cloud

Drweng; Chicago (IL); On-site; USD 175,000 - 210,000; Full time

Benefits offered by this job

Health insurance

401k with discretionary employer match

Disability insurance

Life and AD&D insurance

Vision and dental insurance

Flexible spending accounts

Job summary

DRW, a diversified trading firm headquartered in Chicago, seeks an experienced Windows Server engineer to join our global IT operations. You will manage core Microsoft services and keep critical trading desks online.

The role involves deploying Windows Server environments, integrating Entra ID and Exchange, configuring SSO, and handling incidents with on‑call rotations. Strong scripting, IaC, and networking skills are essential.

Qualifications

• 5+ years managing Windows Server infrastructure in high visibility environments.
• Deep expertise in AD, DNS, DHCP, Failover Clustering and load balancers.
• Hands-on with Entra ID, Exchange (Server/Online/Hybrid), MECM.
• Proficient in scripting (PowerShell, Python), IaC (Terraform, Ansible) and Git.
• Strong networking knowledge and documentation skills.

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 per firmwide change management processes.
• Maintain clear system documentation and repeatable runbooks.
• Participate in a global support team with on‑call rotation and weekend maintenance.

Skills

Windows Server

Active Directory

Group Policy

DNS

DHCP

Failover Clustering

Load Balancers

Entra ID

Exchange (Server/Online/Hybrid)

PowerShell

Python

Terraform

Ansible

Git (GitHub/GitLab)

Networking

Documentation

On-call Support

Job description

DRW, a diversified trading firm headquartered in Chicago, seeks an experienced Windows Server engineer to join our global IT operations. You will manage core Microsoft services and keep critical trading desks online.

The role involves deploying Windows Server environments, integrating Entra ID and Exchange, configuring SSO, and handling incidents with on‑call rotations. Strong scripting, IaC, and networking skills are essential.