Windows Server Lead — Hybrid Infra, High Availability

Chicago Trading Company; Chicago (IL); Hybrid; USD 175,000 - 225,000; Full time

Benefits offered by this job

generous time off

insurance coverage

paid parental leave

free breakfast and lunch (plus healthy

wellness reimbursement

a variety of other benefits focused on

Job summary

Chicago Trading Company (CTC) is seeking a seasoned Windows Server leader to guide and grow a team responsible for high-availability trading infrastructure in Chicago. You will design, implement, and optimize Windows Server solutions with a focus on uptime and low latency for trading workloads.

The role emphasizes automation, hybrid identity, and cross-team collaboration to deliver safe, scalable changes. On-call leadership and strong incident response are key aspects of this position.

Qualifications

• 8+ years of hands-on Windows Server administration experience in high-availability environments.
• Demonstrated leadership running infrastructure teams or as a senior technical lead.
• Strong PowerShell scripting/automation and IaC tooling experience.

Responsibilities

• Lead and develop a team of Windows Server engineers, setting priorities for reliability and platform initiatives.
• Design and implement high-performance Windows Server solutions for latency-sensitive trading workloads.
• Drive automation and infrastructure-as-code practices to improve deployment consistency and scale operations.
• Lead Active Directory modernization and hybrid identity initiatives for secure access.
• Collaborate with Security, Infrastructure, and Development teams to plan and deliver changes safely.
• Improve incident response through leadership during events and root cause analysis.
• Contribute to resource management, forecasting requirements, and performance improvements.
• Produce and maintain runbooks, diagrams, and post-incident reviews.
• Participate in on-call rotation and lead during critical incidents.

Skills

Windows Server administration

Active Directory

Group Policy

DNS

DHCP

Failover Clustering

PowerShell scripting

Infrastructure-as-code

On-call readiness

Leadership

Tools

SCCM/MECM

Monitoring tools

Backup systems

Load balancers

CI/CD

Job description

Chicago Trading Company (CTC) is seeking a seasoned Windows Server leader to guide and grow a team responsible for high-availability trading infrastructure in Chicago. You will design, implement, and optimize Windows Server solutions with a focus on uptime and low latency for trading workloads.

The role emphasizes automation, hybrid identity, and cross-team collaboration to deliver safe, scalable changes. On-call leadership and strong incident response are key aspects of this position.