Windows Server Engineer - Infrastructure

CTC Lateral - Website & LinkedIn•Chicago, IL

1d•$140,000 - $160,000•Hybrid

About The Position

Chicago Trading Company (CTC) is hiring a Windows Server Engineer for its infrastructure team. The role designs and implements Windows Server solutions emphasizing availability, operational excellence, and latency-sensitive trading workloads. It builds and maintains automation and infrastructure-as-code, contributes to Active Directory modernization and Entra ID hybrid identity work, and collaborates with Security, Infrastructure, and Development teams to deliver changes safely. The engineer participates in incident response, root cause analysis, preventive fixes, workload assessment, and performance tuning. The role also maintains runbooks, diagrams, and post-incident reviews and participates in an on-call rotation. Most CTC teams, excluding Trading, follow a hybrid workplace model, subject to change based on business need. The position offers a salary range of $140,000–$160,000 USD and eligibility for an annual discretionary bonus based on individual skills, experience, qualifications, and firm performance.

Requirements

Strong collaboration and communication skills, including selecting an appropriate message and channel for the audience.
A pragmatic approach that balances fast delivery with long-term maintainability and uses sound, data-driven assessment to choose solutions.
Ability to prioritize important work and own issues through to resolution.
At least 3 years of hands-on Windows Server administration experience, ideally in critical, high-availability environments.
Solid working knowledge of Windows Server, Active Directory, Group Policy, DNS, DHCP, and Failover Clustering, including troubleshooting and performance tuning.
Solid PowerShell scripting and automation skills.
Experience with infrastructure-as-code or configuration management tools, or a clear willingness to learn them.
Understanding of how production-system changes affect users and close attention to procedures, change management, and service expectations.
Willingness to participate in an on-call rotation.
Interest in supporting team growth, such as participating in interviews and recruiting.

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, and DevOps/CI/CD practices.
Experience supporting financial services infrastructure, trading systems, or market data platforms.
Exposure to modern deployment approaches such as containerization and orchestration.

Responsibilities

Design and implement components of Windows Server solutions, emphasizing availability, operational excellence, and latency-sensitive trading workloads.
Build and maintain automation and infrastructure-as-code to improve deployment consistency, reduce manual work, and scale operations.
Contribute to Active Directory modernization and Entra ID hybrid identity work.
Collaborate with Security, Infrastructure, and Development teams to plan and deliver changes safely and predictably.
Participate in incident response, troubleshoot problems, contribute to root cause analysis, and implement preventive fixes.
Support workload assessment and performance tuning to ensure systems perform during peak market activity.
Write and maintain runbooks, diagrams, and post-incident reviews.
Participate in an on-call rotation.
Help the team grow, for example by participating in interviews and recruiting.