Windows Server Team Lead

About this role

<div class="content-intro"><p>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.</p> <p>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.</p></div><p data-renderer-start-pos="496" data-local-id="37b234be-5108-4d70-b320-60c7d3fa0963">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.</p> <p id="What-You’ll-Do" data-local-id="741f3df2-b3d0-4036-b50d-2fd3c9051cd3" data-renderer-start-pos="812"><strong data-renderer-mark="true">What You’ll Do</strong></p> <ul> <li data-renderer-start-pos="830" data-local-id="da24644c-9c27-4900-b532-56dc03810fe7">Lead and develop a team of Windows Server engineers, setting priorities and focusing effort on high‑impact reliability and platform initiatives.</li> <li data-renderer-start-pos="978" data-local-id="7da26a16-7665-4f47-97ba-423f3e234a23">Design and implement high‑performance Windows Server solutions with a strong emphasis on availability, operational excellence, and latency‑sensitive trading workloads.</li> <li data-renderer-start-pos="1149" data-local-id="252d4917-722f-4895-af75-acacfe57afaa">Drive automation and infrastructure‑as‑code practices to improve deployment consistency, reduce manual work, and scale operations.</li> <li data-renderer-start-pos="1283" data-local-id="77916074-c16e-4bd4-bfae-0be85f655ee7">Lead Active Directory modernization and hybrid identity initiatives, ensuring secure, reliable access across the firm.</li> <li data-renderer-start-pos="1405" data-local-id="5710ed9d-b038-4fc6-bb06-c02ac53330d8">Partner closely with Security, Infrastructure, and Development teams to plan and deliver changes safely and predictably.</li> <li data-renderer-start-pos="1529" data-local-id="488c8998-881f-4a8d-9313-88930c2db9ad">Improve incident response through clear leadership during events, root cause analysis, and durable preventative follow‑ups.</li> <li data-renderer-start-pos="1656" data-local-id="ff578ce8-3986-461f-b9ea-1b6b30ec550e">Contribute to resource management, forecasting requirements, and enhancing performance to support peak market activity.</li> <li data-renderer-start-pos="1779" data-local-id="bb3f6a10-d0ea-42f7-8588-edaf7e328931">Produce and maintain documentation (runbooks, diagrams, post‑incident reviews) to support knowledge sharing and continuous improvement.</li> <li data-renderer-start-pos="1918" data-local-id="dea9f30b-2a47-479c-bcd5-2eae9bee59c3">Participate in an on‑call rotation and provide leadership during critical incidents as needed.</li> </ul> <p id="What-We’re-Looking-For" data-local-id="beceaf4e-107b-4690-8f88-275f8e5935bc" data-renderer-start-pos="2617"><strong data-renderer-mark="true">What We’re Looking For</strong></p> <ul> <li data-renderer-start-pos="2643" data-local-id="032ebad4-4bfb-48de-b635-07b66238a596">Good interpersonal skills with the ability to lead, mentor, and collaborate across technical teams.</li> <li data-renderer-start-pos="2746" data-local-id="273520f7-c5ff-4586-a70b-06a23a68f1a3">A pragmatic approach that balances fast delivery with long‑term maintainability and operational excellence.</li> <li data-renderer-start-pos="2857" data-local-id="041c3131-cc21-4771-9ebb-9b013b8e0d2a">Ability to triage and resolve issues end‑to‑end, including clear ownership of root cause and prevention.</li> <li data-renderer-start-pos="2965" data-local-id="94aa482a-ed9b-449e-bfd3-f8d255f710e9">8+ years of hands‑on Windows Server administration experience in critical, high‑availability environments.</li> <li data-renderer-start-pos="3075" data-local-id="2b8b229c-6c13-4b87-9776-8fc60da1dad2">Deep expertise in Windows Server, Active Directory, Group Policy, DNS, <span data-highlighted="true" data-vc="highlighted-text"><span class="_kqswh2mm"><span class="_5pioz8co _189e1dm9 _1il9buyh _19lc184f _d0altlke" data-testid="definition-highlighter">DHCP</span></span></span>, and Failover Clustering, including performance tuning and resolving complex challenges.</li> <li data-renderer-start-pos="3243" data-local-id="e6c7aa88-fe8c-4a9a-a3f3-c30fccd2389c">Proven leadership experience running infrastructure teams (or acting as a senior technical lead), with a record of developing engineers and driving standards.</li> <li data-renderer-start-pos="3405"…