Skip to content

Senior Systems Engineer - Microsoft

DRW
🇺🇸Chicago🇺🇸AustinSeniorFull-time$175k–$210kPosted September 16, 2026

About the Role

DRW is a diversified trading firm seeking a Senior Systems Engineer - Microsoft to help administer and support its Microsoft infrastructure across a global support team.

  • Administer core Microsoft services: Active Directory, DNS, DHCP, Group Policy, and Exchange (on-premise, Online, hybrid).
  • Deploy, maintain and support Windows Server environments (2016–2025) and Microsoft cloud services including Entra ID, OneDrive, Copilot, and Microsoft 365.
  • Configure single sign-on and federation using SAML, OAuth/OIDC, and SCIM.
  • Triage and resolve tickets from the operations queue and respond to critical production incidents.
  • Implement planned and ad hoc changes per firmwide change management processes, and capture configurations as repeatable runbooks.
  • Participate in a global support team with on-call rotation and occasional weekend maintenance.

Requirements

  • 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 (e.g. 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. 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
  • Experience with Splunk, Grafana, Alertmanager, Prometheus (bonus)
  • Familiarity with containerization and Kubernetes (bonus)
  • Prior experience in the trading or financial services industry (bonus)

What You'll Get

  • $175k–$210k base salary
  • 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