Windows Server Team Lead

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.

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.

• 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.

• 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 Power Shell 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.

• 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 Dev Ops/CI/CD practices.
• Experience supporting financial services infrastructure, trading systems, or market data platforms.
• Exposure to modern deployment approaches (e.g., containerization, orchestration).

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.

Salary Range: $175,000 – $225,000 USD per year. The role is also eligible for an annual discretionary bonus based on performance.

We offer generous time off, insurance coverage, paid parental leave, free breakfast and lunch, wellness reimbursement, and a variety of other benefits focused on providing the best employee experience.

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, please contact us at