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Systems Engineer - Microsoft

DRW
πŸ‡ΊπŸ‡ΈChicagoMediorFull-time$120k–$160kPosted September 11, 2026

About the Role

DRW is a diversified trading firm seeking a Systems Engineer - Microsoft to join its global support team. The role focuses on administering core Microsoft services and Windows Server environments that support trading desks and business teams.

  • Administer core Microsoft services including Active Directory, DNS, DHCP, Group Policy, and Exchange (on-premise, Online, hybrid).
  • Deploy, maintain and support Windows Server environments (2016–2025).
  • Support Microsoft cloud services such as Entra ID, OneDrive, Copilot and Microsoft 365.
  • Configure single sign-on and federation (SAML, OAuth/OIDC, SCIM).
  • Triage and resolve operations queue tickets and respond to critical production incidents.
  • Implement planned and ad hoc changes following 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.

Requirements

  • 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 (e.g. 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
  • You are eager to learn, collaborate, and find solutions under interesting constraints
  • Experience with Splunk, Grafana, Alertmanager, Prometheus
  • Familiarity with DevOps/CI CD and IaC practices, containerization and Kubernetes
  • Prior experience in the trading or financial services industry

What You'll Get

  • $120k–$160k base salary
  • Group medical, pharmacy, dental and vision insurance
  • 401k (with discretionary employer match)
  • Short and long-term disability insurance
  • Life and AD&D insurance
  • Health savings accounts
  • Flexible spending accounts