Senior Systems Engineer - Microsoft

DRW; Chicago (IL); On-site; USD 175,000 - 210,000; Full time

Benefits offered by this job

Group medical

Pharmacy

Dental and vision insurance

401k with discretionary employer match

Short and long-term disability

Life and AD&D insurance

Health savings accounts

Flexible spending accounts

Job summary

DRW is seeking an experienced Windows Server specialist to manage and optimize core Microsoft environments across on-prem, hybrid and cloud services. You will handle Active Directory, DNS, DHCP, Group Policy, Exchange and MECM, while scripting with PowerShell and Python and using IaC tools for repeatable deployments.

The role requires strong networking, virtualization and documentation skills, with on-call rotation and occasional weekend work.

Qualifications

• 5+ years managing Windows Server infrastructure in mission-critical environments.
• Deep expertise in AD, DNS, DHCP, Group Policy, Failover Clustering and load balancers.
• Hands-on with Entra ID, Exchange Server/Online/Hybrid, MECM/SCCM.
• Scripting with PowerShell and Python; IaC with Terraform/Ansible; GitHub/GitLab/Bitbucket.
• Strong networking, server hardware and hypervisor/VM deployment experience.
• Excellent documentation and ability to turn ad hoc tasks into repeatable processes.
• Proven ability to troubleshoot under pressure; trading/low latency envs a plus.

Responsibilities

• Administer core Microsoft services: Active Directory, DNS, DHCP, Group Policy, Exchange (on-premise, Online, hybrid).
• Deploy, maintain and support Windows Server environments (2016–2025).
• Support Microsoft cloud services (Entra ID, OneDrive, Copilot, Microsoft 365).
• Configure single sign-on and federation (SAML, OAuth/OIDC, SCIM).
• Triage and resolve tickets from operations queue; respond to critical production incidents.
• Implement planned and ad hoc changes per firmwide change management.
• Maintain system documentation and repeatable runbooks.
• Participate in global support with on-call rotation and weekend maintenance.

Skills

Windows Server

Active Directory

DNS

DHCP

Group Policy

Entra ID

Exchange Server/Online/Hybrid

MECM (SCCM)

PowerShell

Python

Terraform

Ansible

GitHub/GitLab/Bitbucket

Scripting

Networking

Hypervisor/VM deployments

Tools

Splunk

Grafana

Prometheus

Kubernetes

Job description

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk.

Headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia, we trade a variety of asset classes including Fixed Income, ETFs, Equities, FX, Commodities and Energy across all major global markets. We have also leveraged our expertise and technology to expand into three non-traditional strategies: real estate, venture capital and cryptoassets.

We operate with respect, curiosity and open minds. The people who thrive here share our belief that it’s not just what we do that matters- it's how we do it. DRW is a place of high expectations, integrity, innovation and a willingness to challenge consensus.

Our Philosophy

• We believe in relentless automation of repetitive tasks.


• We have the curiosity and drive to dig deep and find creative solutions.


• We believe our goal is to find the right solution rather than always being right.


• We provide exceptional customer service to our teams and trading desks.


• We care more that the right thing is done than about rigid job descriptions or boundaries.

What You’ll Do

• Administer core Microsoft services: Active Directory, DNS, DHCP, Group Policy, Exchange (on-premise, Online, hybrid).


• Deploy, maintain and support Windows Server environments (2016-2025).


• Support Microsoft cloud services (Entra ID, OneDrive, Copilot, Microsoft 365 services).


• Configure single sign on and federation (SAML, OAuth/OIDC, SCIM).


• Triage and resolve tickets from the operations queue; respond to critical production incidents.


• Implement planned and ad hoc changes in accordance with firmwide change management processes.


• Maintain clear system documentation and capture specialized configurations as repeatable runbooks.


• Participate in a global support team with on call rotation and occasional weekend maintenance.

Your Background

• 5+ years managing Windows Server infrastructure in high visibility, mission critical environments.


• Deep expertise in Windows Server services: Active Directory, Group Policy, DNS, DHCP, Failover Clustering, load balancers.


• Hands on experience with Entra ID, Exchange (Server/Online/Hybrid), MECM (SCCM).


• Proficient with scripting (PowerShell, Python), IAC (e.g. Terraform, Ansible) and version control (GitHub, GitLab, Bitbucket).


• Strong networking knowledge and experience with server hardware and hypervisor/VM deployments.


• Excellent documentation and knowledge management skills; ability to turn ad hoc tasks into documented, repeatable processes.


• Proven ability to troubleshoot and resolve critical issues under pressure (trading/low latency environments a plus).


• Strong written and verbal communication skills. You can work across teams and have evidence-based discussions on technical and operational topics


• You are eager to learn, collaborate, and find solutions under interesting constraints

Bonus Points If You Have

• Experience with Splunk, Grafana, Alertmanager, Prometheus


• Familiarity with containerization and Kubernetes.


• Prior experience in the trading or financial services industry.

The annual base salary range for this position is $175,000 to $210,000 depending on the candidate’s experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus.

• group medical


• pharmacy


• dental and vision insurance


• 401k (with discretionary employer match)


• short and long-term disability


• life and AD&D insurance


• health savings accounts


• flexible spending accounts

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