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Desktop Systems Engineer

$130k - $160k

DRW Holdings, LLC

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk.

Headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia, we trade a variety of asset classes including Fixed Income, ETFs, Equities, FX, Commodities and Energy across all major global markets. We have also leveraged our expertise and technology to expand into three non-traditional strategies: real estate, venture capital and cryptoassets.

We operate with respect, curiosity and open minds. The people who thrive here share our belief that it’s not just what we do that matters–it's how we do it. DRW is a place of high expectations, integrity, innovation and a willingness to challenge consensus.

Our  Desktop Systems Engineering team is the front line of support for all users across the firm. We work with a wide range of the best technology available and we get to test, configure and deploy it all in an environment that continually challenges us and demands that we learn new things daily. The team is also responsible for driving innovation for technologies that impact users daily. The pace is fast but we also obsess about leaving no stone unturned when there is a problem to be solved. We believe in healthy debate, creative and collaborative problem solving and active knowledge sharing. Strong technical aptitude and a passion for technology are critical for success in the Systems Engineer role but initiative, strong analytics and drive are equally important.

What you’ll be doing:

  • Provide advanced desktop support for Windows, macOS, and Linux environments across corporate offices and remote users.
  • Build, configure, deploy, maintain, and upgrade desktops, laptops, virtual machines, and mobile devices.
  • Troubleshoot hardware, software, operating system, networking, and peripheral issues in a timely manner.
  • Manage user provisioning and deprovisioning, including Active Directory accounts, email access, VPN access, MFA, permissions, and security groups.
  • Support and maintain conference room technologies, AV systems, Zoom/Teams rooms, and collaboration platforms.
  • Monitor desktop infrastructure health and proactively address performance, security, and compliance issues.
  • Work closely with networking, security, storage, cloud, and infrastructure teams on cross‑functional projects and escalations.
  • Evaluate, test, and recommend new hardware, software, and endpoint technologies.
  • Maintain accurate documentation for systems, processes, troubleshooting procedures, and asset inventory.
  • Support office moves, desk setups, hardware refreshes, and enterprise technology rollouts.
  • Assist with onboarding, offboarding, and transfer processes for employees and contractors.
  • Participate in after‑hours support, maintenance windows, and on‑call rotations as required.

  What we’re looking for in this role:

  • Solid experience with workstations and laptops, including adding display cards and network interface cards (NICs), swapping chasis. Able to lift 50-60 lbs.
  • Efficient in desk moves, always maintaining a positive attitude.
  • Strong background in imaging, supporting, and configuring Windows 11 for optimal performance.
  • Proficient in enterprise drive encryption with BitLocker and MBAM, ensuring security in all tasks.
  • Experienced in supporting Microsoft Office Suite (especially Outlook and Excel) and familiar with plugins.
  • Knowledgeable in mobile device management through AirWatch.
  • Experienced with Microsoft Exchange and Apple Business Manager for cross-platform support.
  • At least 2 years in MEMCM/SCCM administration or similar roles.
  • Robust skills in virtualization and desktop services with up-to-date technology knowledge.
  • Might have to visit our Greenwich Connecticut office once a month and during holidays or when other team members are off to provide coverage.
  • Proficient in using Zoom and conference room equipment to help with meetings to colleagues and visitors
  • An enthusiastic self-starter who thrives under pressure, values teamwork, and has excellent communication skills.

  Nice to have:

  • Intune management experience
  • Previous macOS or Linux support experience
  • Previous Windows Server and Active Directory support experience
  • Scripting or low level programming experience

The annual base salary range for this position is $130,000 to $160,000 depending on the candidate’s experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus. In addition, DRW offers a comprehensive suite of 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.

For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at

California residents, please review the California Privacy Notice for information about certain legal rights at

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