Windows Server Team Lead

CTC Lateral - Website & LinkedIn; Chicago (IL); On-site; USD 175,000 - 225,000; Full time

Benefits offered by this job

Generous time off

Insurance coverage

Wellness reimbursement

Free breakfast and lunch

Job summary

CTC Lateral seeks a Windows Server Team Lead based in Chicago. You will lead a team focused on designing and implementing scalable Windows Server solutions, driving automation, and ensuring operational excellence. Ideal candidates have over 8 years in Windows Server administration and strong leadership skills.

We emphasize collaboration with other technical teams and offer a competitive salary between $175,000 and $225,000, along with various employee benefits including generous time off and wellness reimbursement.

Qualifications

• 8+ years of hands-on Windows Server administration experience.
• Ability to lead, mentor, and collaborate across technical teams.
• Strong PowerShell scripting and automation skills.

Responsibilities

• Lead and develop a team of Windows Server engineers.
• Design and implement high-performance Windows Server solutions.
• Drive automation and infrastructure-as-code practices.

Skills

Windows Server administration

Active Directory

PowerShell scripting

Team leadership

Infrastructure automation

Job description

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.

Role Overview

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

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

Benefits

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.

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, please contact us at [e-mail].