DRW is a technology-driven, diversified principal trading firm. We trade our own capital at our own risk, across a broad range of asset classes, instruments and strategies, in financial markets around the world. As the markets have evolved over the past 25 years, so has DRW – maximizing opportunities to include real estate, cryptoassets and venture capital. With over 1,000 employees at our Chicago headquarters and offices around the world, we work together to solve complex problems, challenge consensus and deliver meaningful results. It’s a place of high expectations, deep curiosity and thoughtful collaboration. 

We are seeking a Senior Systems Engineer to deploy, administer and support Windows, VMWare and Storage systems as well as a variety of cloud-based services. Members of the Core Infrastructure Services team are dedicated to providing reliable, flexible services which are utilized by the entire firm for many business-critical activities.


  • Administer core infrastructure services including Active Directory, DNS, DHCP, Group Policy, Exchange, RemoteApp, SCCM/SCOM, backup/recovery and compliance, file servers and permissions, certificates, enterprise storage systems, NetBackup, enterprise communication, VMware, Veeam, vCenter, load balancers.
  • Manage cloud platforms including AWS, Azure, and Office 365.
  • Deploy and administer physical and virtual Windows servers, VMWare host servers, and storage to support these systems.
  • Perform problem resolutions, root cause analysis, and implement projects to reduce future issues for the above systems and technologies.
  • General administration of shared folders, group policy, DNS records, VM deployments, storage expansion and cleanup, and various other day-to-day activities.
  • Implement automation and scripting via PowerShell and Python to reduce manual tasks and provide proactive alerting to get ahead of outages.
  • Research, test, and implement new/updated technologies.
  • Act as point of escalation to service desk for more complex issues.
  • Work with other teams within the organization on hardware specifications and provisioning.
  • Document systems and specialized configurations for ease of support within team.


  • 5+ years of experience administering Windows Server and associated services, VMWare, and storage.
  • Experience with cloud providers including Microsoft Office 365, Azure AD, and AWS and/or a strong desire to learn
  • Solid knowledge of and previous experience using scripting technologies (i.e. PowerShell)
  • Strong knowledge of network protocols and technologies.
  • Experience maintaining/deploying/configuring server hardware.
  • Proven ability to troubleshoot and resolve production problems while making sensible decisions in times of stress.
  • Previous experience working in the trading industry a plus
  • Excellent verbal and written communication skills
  • Must have excellent documentation and knowledge management skills

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