Windows Server Engineer - Infrastructure

Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options market making.  Our collaborative culture fuels innovation in quantitative research, systematic trading strategies, and cutting-edge trading technology.  For over three decades CTC has provided critical liquidity across derivatives exchanges worldwide - making them fairer, more transparent, and more efficient.

We strive to be the most innovative firm in the industry today, tomorrow, and long into the future while upholding ethical excellence. We believe that CTC makes a positive impact on the markets, the lives of our employees, and all the communities to which we belong. Started in 1995 by a team of forward-thinking Traders, we are proud to call ourselves an industry leader that keeps making markets and each other better.

WHAT YOU'LL DO

• Design and implement components of Windows Server solutions, with a strong emphasis on availability, operational excellence, and latency-sensitive trading workloads.
• Build and maintain automation and infrastructure-as-code to improve deployment consistency, reduce manual work, and scale operations.
• Contribute to Active Directory modernization and Entra ID hybrid identity work, helping keep access across the firm secure and reliable.
• Work with Security, Infrastructure, and Development teams to plan and deliver changes safely and predictably.
• Take part in incident response: solve problems, contribute to root cause analysis, and follow through on preventive fixes.
• Support workload assessment and performance tuning so systems hold up during peak market activity.
• Write and maintain documentation (runbooks, diagrams, post-incident reviews) to support information exchange and continuous improvement.
• Participate in an on-call rotation.

WHAT WE'RE LOOKING FOR

• Strong collaboration and communication skills, including picking the right message and channel for the audience.
• A pragmatic approach that balances fast delivery with long-term maintainability, and chooses solutions based on sound, data-driven assessment.
• Ability to prioritize what matters most and to own issues through to resolution.
• 3+ years of hands-on Windows Server administration experience, ideally in critical, high-availability environments.
• Solid working knowledge of Windows Server, Active Directory, Group Policy, DNS, DHCP, and Failover Clustering, including resolving issues and performance tuning.
• Solid PowerShell scripting and automation skills. Experience with infrastructure-as-code or configuration management tools, or a clear willingness to learn them.
• Understanding of how changes to production systems affect users, and close attention to procedure, change management, and service expectations.
• Willingness to participate in an on-call rotation.
• Interest in helping the team grow, for example by taking part in interviews and recruiting.

NICE TO HAVE

• Experience with enterprise platforms such as SCCM/MECM, endpoint/server monitoring, backup systems, and/or load balancers.
• Familiarity with ITILconcepts, operational workflows, and DevOps/CI/CD practices.
• Experience supporting financial services infrastructure, trading systems, or market data platforms.
• Exposure to modern deployment approaches (e.g., containerization, orchestration).

COMPENSATION

The salary range for this role is listed below. This role is also eligible for an annual discretionary bonus. The discretionary bonus will be dependent upon the individual’s skills, experience, qualifications, and firm performance. 

Salary Range

$140,000—$160,000 USD

Most teams at CTC, with the exception of Trading, follow a hybrid workplace model, subject to change based on business need.

OUR BENEFITS 

We strongly believe in the well-being of our employees and their families so we offer outstanding benefits to support you both professionally and personally. These benefits include generous time off, insurance coverage, paid parental leave, free breakfast and lunch (plus healthy snacks, of course), wellness reimbursement, and a variety of other benefits focused on providing the best employee experience. 

(Disclaimer: interns and contractors are not eligible for benefits at CTC) 

OUR COMMITMENT TO DIVERSITY, EQUITY and INCLUSION

At CTC, we aim to cultivate a workplace that celebrates diversity and each person feels included, engaged and empowered. Where each of us feels we belong. We are committed to having a diverse workforce and are proud to be an equal opportunity employer. CTC does not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform crucial job functions, and to receive other benefits and privileges of employment. 

If you have a disability and believe you need a reasonable accommodation in order to search for a job opening or to apply for a position, please contact us at [email protected]. Note that emails sent to this email account for non-disability related issues, such as following up on an application, will not receive a response.

USE OF ARTIFICIAL INTELLIGENCE (AI)

Information submitted by job applicants may be subject to review and analysis by automated systems, including Artificial Intelligence (AI), as part of the recruitment process. Such systems are utilized to enhance the efficiency and effectiveness of our hiring procedures. Applicants are advised that any information provided may be evaluated by AI tools to ensure an equitable and thorough assessment.