Windows Server Team Lead

Windows Server Team Lead - Proprietary Trading Firm in Chicago, IL

The Firm:

My client is a proprietary trading firm specializing in options market making, with three decades of history providing liquidity across derivatives exchanges worldwide. The firm is privately held, trading its own capital, with a strong internal engineering culture supporting its trading business.

The Role:

We are helping them on their search for a Windows Server Team Lead within their Infrastructure team in Chicago to design, build, and operate scalable systems supporting the business. The role covers Windows server platforms, identity services, automation, and reliability engineering across on-prem Windows environments and hybrid cloud integrations, with direct exposure to latency-sensitive trading workloads.

What You'll Do:

• Lead and develop a team of Windows Server engineers, setting priorities across high-impact reliability and platform initiatives
• Design and implement 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 and reduce manual work
• Lead Active Directory modernization and hybrid identity initiatives
• Partner with Security, Infrastructure, and Development teams to plan and deliver changes safely
• Lead incident response, root cause analysis, and preventative follow-up
• Contribute to resource forecasting and performance planning to support peak market activity
• Maintain documentation (runbooks, diagrams, post-incident reviews)
• Participate in an on-call rotation, including leadership during high-severity incidents

What We're Looking For:

• 8+ years of hands-on Windows Server administration in high-availability, mission-critical environments
• Deep expertise in Windows Server, Active Directory, Group Policy, DNS, DHCP, and Failover Clustering, including performance tuning
• Proven leadership running infrastructure teams, or acting as a senior technical lead, with a record of developing engineers and setting standards
• Strong PowerShell scripting/automation skills; experience with infrastructure-as-code or configuration management tools
• Ability to own issues end-to-end, from triage through root cause and prevention
• Comfortable with on-call rotation and leading through high-severity incidents
• Disciplined approach to change management and service expectations

Nice to Have:

• Experience with SCCM/MECM, endpoint/server monitoring, backup systems, or load balancers
• Familiarity with ITIL, DevOps/CI/CD practices
• Experience supporting financial services infrastructure, trading systems, or market data platforms
• Exposure to containerization/orchestration

Location & Working Model:

This role is based in Chicago, working closely with Infrastructure, Security, Networking, and Development. Most teams operate a hybrid model with an emphasis on in-person collaboration.

Compensation & Benefits:

Base salary range: $175k-$225k USD , plus an annual discretionary bonus based on individual performance and firm results. Benefits include generous PTO, comprehensive insurance coverage, paid parental leave, and wellness reimbursement.

If this sounds like you - or you know someone who could be a good fit for the position - please get in touch!

(The client is an equal opportunity employer).