Senior Windows Platform Engineer — Global, High-Impact IT

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

Benefits offered by this job

Group medical

Pharmacy

Dental and vision insurance

401k with discretionary employer match

Short and long-term disability

Life and AD&D insurance

Health savings accounts

Flexible spending accounts

Job summary

DRW is seeking an experienced Windows Server specialist to manage and optimize core Microsoft environments across on-prem, hybrid and cloud services. You will handle Active Directory, DNS, DHCP, Group Policy, Exchange and MECM, while scripting with PowerShell and Python and using IaC tools for repeatable deployments.

The role requires strong networking, virtualization and documentation skills, with on-call rotation and occasional weekend work.

Qualifications

• 5+ years managing Windows Server infrastructure in mission-critical environments.
• Deep expertise in AD, DNS, DHCP, Group Policy, Failover Clustering and load balancers.
• Hands-on with Entra ID, Exchange Server/Online/Hybrid, MECM/SCCM.
• Scripting with PowerShell and Python; IaC with Terraform/Ansible; GitHub/GitLab/Bitbucket.
• Strong networking, server hardware and hypervisor/VM deployment experience.
• Excellent documentation and ability to turn ad hoc tasks into repeatable processes.
• Proven ability to troubleshoot under pressure; trading/low latency envs a plus.

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 operations queue; respond to critical production incidents.
• Implement planned and ad hoc changes per firmwide change management.
• Maintain system documentation and repeatable runbooks.
• Participate in global support with on-call rotation and weekend maintenance.

Skills

Windows Server

Active Directory

DNS

DHCP

Group Policy

Entra ID

Exchange Server/Online/Hybrid

MECM (SCCM)

PowerShell

Python

Terraform

Ansible

GitHub/GitLab/Bitbucket

Scripting

Networking

Hypervisor/VM deployments

Tools

Splunk

Grafana

Prometheus

Kubernetes

Job description

DRW is seeking an experienced Windows Server specialist to manage and optimize core Microsoft environments across on-prem, hybrid and cloud services. You will handle Active Directory, DNS, DHCP, Group Policy, Exchange and MECM, while scripting with PowerShell and Python and using IaC tools for repeatable deployments.

The role requires strong networking, virtualization and documentation skills, with on-call rotation and occasional weekend work.