Senior Windows Systems Engineer – Global On-Call Automation

P2P; Chicago (IL); On-site; USD 175,000 - 210,000; Full time

Benefits offered by this job

Group medical insurance

Dental and vision insurance

401k with discretionary match

Disability insurance

Life insurance

Health savings accounts

Job summary

DRW is a leading trading firm headquartered in Chicago, seeking an experienced Windows Server Infrastructure Engineer to manage core Microsoft services, deploy and maintain server environments, and support cloud and on‑prem ecosystems. The role requires hands‑on proficiency with AD, Exchange, MECM, scripting, and IaC, in a high‑pressure trading setting.

You will join a global support team with on‑call rotations, contribute to runbooks, and help ensure reliability across critical systems across

Qualifications

• 5+ years managing Windows Server infrastructure in high visibility, mission critical environments.
• Deep expertise in Windows Server services: Active Directory, Group Policy, DNS, DHCP, Failover Clustering, load balancers.
• Hands on experience with Entra ID, Exchange (Server/Online/Hybrid), MECM (SCCM).
• Proficient with scripting (PowerShell, Python), IAC (Terraform, Ansible) and version control (GitHub, GitLab, Bitbucket).
• Strong networking knowledge and experience with server hardware and hypervisor/VM deployments.
• Excellent documentation and knowledge management skills; ability to turn ad hoc tasks into documented, repeatable processes.
• Proven ability to troubleshoot and resolve critical issues under pressure (trading/low latency environments a plus).
• Strong written and verbal communication 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 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

Group Policy

DNS

DHCP

Failover Clustering

Load Balancers

Entra ID

Exchange (Server/Online/Hybrid)

MECM (SCCM)

PowerShell

Python

Terraform

Ansible

GitHub/GitLab/Bitbucket

Scripting

Networking

Documentation

Troubleshooting under pressure

Trading/low latency awareness

Tools

Splunk

Grafana

Alertmanager

Prometheus

Kubernetes

Job description

DRW is a leading trading firm headquartered in Chicago, seeking an experienced Windows Server Infrastructure Engineer to manage core Microsoft services, deploy and maintain server environments, and support cloud and on‑prem ecosystems. The role requires hands‑on proficiency with AD, Exchange, MECM, scripting, and IaC, in a high‑pressure trading setting.

You will join a global support team with on‑call rotations, contribute to runbooks, and help ensure reliability across critical systems across