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Windows Server Team Lead

Chicago Trading Company · Chicago, IL · Technology

Posted Sep 11, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a PowerShell automation or infrastructure-as-code effort you drove. What manual process did it replace and how did you get the rest of the team to actually adopt it?

What they are checking: whether automation work was personally driven and sustained, not a one-off script

Describe a time you had to lead a team through a high-severity incident. What did you personally do versus delegate, and how did the postmortem change something concrete afterward?

What they are checking: leadership presence during pressure and whether root cause work leads to durable fixes

Tell me about a time you had to develop or coach an engineer who was struggling. What did you actually do differently with them?

What they are checking: substance behind claimed people-management experience

Tell me about a documentation or runbook effort you started from scratch. What made you decide it was needed, and did people actually use it later?

What they are checking: whether they value knowledge sharing as an operational habit, not an afterthought

What would you do

Say a domain controller starts throwing replication errors at 2am during active trading hours. What do you check first and how do you decide whether to fail over or fix in place?

What they are checking: practical incident triage instincts under time pressure with real business stakes

You've got a Security team pushing for a change that Development says will break their deployment pipeline, and Infrastructure needs it done by end of week. How do you handle that?

What they are checking: cross-team negotiation skill and how they balance competing priorities without stalling

What's your process for change management in an environment where a bad change during market hours has real financial consequences?

What they are checking: discipline around procedure and risk awareness, not just technical skill

How do you decide when to accept technical debt to ship something fast versus when to insist on doing it right the first time?

What they are checking: the pragmatic delivery-versus-maintainability judgment the posting explicitly calls for

About the work

Tell me about the largest Windows Server environment you've run day to day. How many servers, what was the availability requirement, and what broke most often?

What they are checking: whether their scale and reliability bar actually matches a latency-sensitive trading environment

Walk me through an Active Directory modernization or migration you led. What was the starting state, what did you change, and how did you keep authentication working during the cutover?

What they are checking: real hands-on depth with AD modernization versus reading about it

How would you tune Failover Clustering and Windows Server for a workload where a few extra milliseconds of latency actually costs the firm money?

What they are checking: depth on performance tuning specific to latency-sensitive systems, not generic HA knowledge

Group Policy and DNS issues can be quiet killers. Tell me about the trickiest one you diagnosed and what the actual root cause turned out to be.

What they are checking: genuine troubleshooting depth on core Windows services versus surface familiarity

How do you approach forecasting resource needs ahead of a known peak, like an expiration day or a high-volume market event?

What they are checking: operational planning maturity beyond reactive firefighting

Have you worked with hybrid identity, connecting on-prem AD to cloud services? What was the trickiest part of keeping that secure and reliable?

What they are checking: specific hybrid cloud identity experience called out in the posting versus pure on-prem background

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The full job description

As published by Chicago Trading Company.

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. As a Windows Server Team Lead, you will work within Infrastructure to design, build, and operate scalable systems that support the business. Your focus will be on Windows server platforms, identity services, automation, and reliability engineering across on‑prem Windows environments and hybrid cloud integrations. What You’ll Do • Lead and develop a team of Windows Server engineers, setting priorities and focusing effort on high‑impact reliability and platform initiatives. • Design and implement high‑performance Windows Server solutions with a strong emphasis on availability, operational excellence, and latency‑sensitive trading workloads. • Drive automation and infrastructure‑as‑code practices to improve deployment consistency, reduce manual work, and scale operations. • Lead Active Directory modernization and hybrid identity initiatives, ensuring secure, reliable access across the firm. • Partner closely with Security, Infrastructure, and Development teams to plan and deliver changes safely and predictably. • Improve incident response through clear leadership during events, root cause analysis, and durable preventative follow‑ups. • Contribute to resource management, forecasting requirements, and enhancing performance to support peak market activity. • Produce and maintain documentation (runbooks, diagrams, post‑incident reviews) to support knowledge sharing and continuous improvement. • Participate in an on‑call rotation and provide leadership during critical incidents as needed. What We’re Looking For • Good interpersonal skills with the ability to lead, mentor, and collaborate across technical teams. • A pragmatic approach that balances fast delivery with long‑term maintainability and operational excellence. • Ability to triage and resolve issues end‑to‑end, including clear ownership of root cause and prevention. • 8+ years of hands‑on Windows Server administration experience in critical, high‑availability environments. • Deep expertise in Windows Server, Active Directory, Group Policy, DNS, DHCP , and Failover Clustering, including performance tuning and resolving complex challenges. • Proven leadership experience running infrastructure teams (or acting as a senior technical lead), with a record of developing engineers and driving standards. • Strong PowerShell scripting/automation skills; experience with infrastructure‑as‑code tools and/or configuration management (or demonstrated willingness to adopt and lead these efforts). • Willingness to participate in an on‑call rotation and lead through high‑severity incidents. • Meticulous attention to procedure, change management, and meeting service expectations. Nice to Haves • Experience with enterprise platforms such as SCCM / MECM , endpoint/server monitoring, backup systems, and/or load balancers. • Familiarity with ITIL concepts, operational workflows, project management, 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). Work Location and Collaboration This role is based in Chicago , working closely with Infrastructure, Security, Networking, and Development teams for high‑bandwidth collaboration. We value face‑to‑face teamwork and pragmatic flexibility. 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 $175,000 — $225,000 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 info@chicagotrading.com. 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.

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