Desktop Systems Engineer
DRW
Chicago, IL · Posted October 28, 2026
Just laid off? Start here: a plan for the first weeks
More in Illinois job market · Energy & Utilities · Engineering jobs
More roles at DRW
- US Trading Analyst · Houston, TX
- Data Analyst, Stewardship · Chicago, IL
- Software Engineer - Cumberland/Options Front Office Systems · New York, NY
- Senior Power Strategist - Load · New York, NY
- Senior Software Engineer - DeFi · Chicago, IL
- Software Developer · Chicago, IL
Where Chicago, IL ranks
Where Chicago, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about engineering jobs
- Best cities for software and engineering jobs #1 San Francisco (3,412 openings)
- Best cities for engineering pay after cost of living #1 San Mateo ($216k)
- Most requested AI skills in engineering jobs #1 AI tools in daily work (6.1%)
- AI tools named most often in engineering jobs #1 Claude (1.7%)
- Employers with the most engineering jobs #1 Amazon (2,992 roles)
How AI is used in this kind of work
Among computer user support specialists, AI is already used for a large share of the tasks. Measured exposure for computer user support specialists: 47% (high).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
Skills this job asks for
Say which you have and which you want to build. We use it to match you to jobs like this one.
About the job
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:
Providing end-user support to employees in the Chicago corporate office and exchange floors
Building, configuring, and upgrading workstations, laptops, and mobile devices
Troubleshooting, maintenance, and upgrades of desktop managed servers
User provisioning (user accounts, mobile devices, VPN, directory permissions)
Providing support for conference room technologies
Automation of repetitive system administration tasks
Evaluating and recommending new hardware and software technologies or solutions
What we’re looking for in this role:
2+ years of MEMCM/SCCM administration experience or similar
Knowledge of application packaging and management
Strong experience supporting and configuring Windows 11
Strong knowledge of Group Policy management
Powershell experience
Passionate about technology
Highly motivated, self-starter who is eager to grow within our organization
Ability to manage projects independently
Previous mobile device management experience
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 $85,000 to $125,000 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 https://drw.com/privacy-notice .
California residents, please review the California Privacy Notice for information about certain legal rights at https://drw.com/california-privacy-notice .
[#LI-LD1]