Senior Systems Engineer - Microsoft

As a Senior Systems Engineer at DRW, you administer and support core Microsoft infrastructure that powers a diversified trading firm operating across fixed income, equities, FX, commodities and cryptoassets. You join a global support team managing mission-critical Windows Server environments and cloud services for trading desks and operations worldwide.

What you'll do

• Administer core Microsoft services including Active Directory, DNS, DHCP, Group Policy, and Exchange (on-premise, Online, and hybrid).
• Deploy, maintain and support Windows Server environments (2016-2025).
• Support Microsoft cloud services including Entra ID, OneDrive, Copilot, and Microsoft 365 services.
• 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 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.

What you bring

• 5+ years managing Windows Server infrastructure in high-visibility, mission-critical environments.
• Deep expertise in Windows Server services including Active Directory, Group Policy, DNS, DHCP, Failover Clustering, and load balancers.
• Hands-on experience with Entra ID, Exchange (Server/Online/Hybrid), and MECM (SCCM).
• Proficiency with scripting (PowerShell, Python), infrastructure as code (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.
• Strong written and verbal communication skills; you can work across teams and engage in evidence-based discussions on technical and operational topics.
• Eagerness to learn, collaborate, and find solutions under interesting constraints.

Nice to have

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

What we offer

• Annual base salary of $175,000 to $210,000 depending on experience and qualifications.
• Eligibility for an annual discretionary bonus.
• Comprehensive employee benefits including 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, and flexible spending accounts.

About DRW

DRW is a diversified trading firm with over 30 years of experience, headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia. The firm trades fixed income, ETFs, equities, FX, commodities and energy across global markets, and has expanded into real estate, venture capital, and cryptoassets.