Systems Engineer

DRW, Chicago

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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 nearly 900 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 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 Amazon and Microsoft 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
  • Proven ability to learn; passion for new technologies
  • Must have strong work ethic and initiative, ability to manage allocation of time.

About DRW

DRW was founded by Don Wilson, who got his start trading on the floor of the Chicago Mercantile Exchange in the late 1980s. Every trader on the floor had a three letter acronym for identification—Don chose his initials, DRW, and the name stuck. Over the past 25 years, DRW has expanded globally while staying true to what has always set us apart…our ability to identify and capture opportunities by leveraging technology, research and risk management. Our Approach We characterize our trading activity as following three general approaches — Liquidity providing: making markets, buying and selling products every day, with execution on a trading floor, over the phone and electronically Risk taking: doing our homework, formulating a view and putting on a position. Some positions are held for a few days, some for a few months or even years. Latency sensitive: combining research and risk management with superior technology and execution Trading in any asset class might include just one of these or may bring together all three; it all depends on what we see as the right strategy in that market. Our knowledge of the markets, pricing and modeling skills, risk management, and leading technology work together to create liquidity, improve market efficiency, and capture opportunities. Our Culture DRW combines the best of both worlds: the opportunity and spirit of a startup and the stability of an established, experienced firm. Our employees work hard to solve interesting problems, and their results are rewarded. We value continuous learning—from our outcomes, from the environment and from each other. It’s a place of high expectations, deep curiosity, and constant collaboration, with some of the smartest, most passionate people you’ll meet.

Want to learn more about DRW? Visit DRW's website.