Systems Engineer - Microsoft

DRW Holdings, LLC.; Chicago (IL); On-site; USD 120,000 - 160,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

401k with discretionary employer match

Disability insurance (short/long-term)

Life and AD&D insurance

Health Savings Account

Job summary

DRW is seeking an experienced Windows Server Administrator in Chicago to manage core Microsoft services, deploy and support Windows Server environments (2016–2025), and oversee cloud services Entra ID, OneDrive, and Microsoft 365. You will configure SSO/federation and triage critical production incidents.

Join a global on-call rotation, maintain runbooks, and collaborate across teams. The role emphasizes automation, scripting in PowerShell and Python, and a proactive approach to changes in a

Qualifications

• Experience managing Windows Server infrastructure in high visibility, mission critical environments.
• Experience administering Windows Server services: Active Directory, Group Policy, DNS, DHCP, Failover Clustering.
• Experience with Entra ID, Exchange (Server/Online/Hybrid) and MECM (SCCM) is preferred.
• You can use scripts (e.g. PowerShell, Python) to automate routine administrative tasks.
• Knowledge of networking fundamentals, server hardware and VM deployments.
• 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.

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 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.

Skills

Active Directory

DNS

DHCP

Group Policy

Exchange

PowerShell

Python

Scripting

Entra ID

MECM/SCCM

Networking fundamentals

VM deployments

Documentation

On-call support

Tools

Splunk

Grafana

Alertmanager

Prometheus

DevOps / CI/CD

IaC

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:

• Experience managing Windows Server infrastructure in high visibility, mission critical environments.
• Experience administering Windows Server services: Active Directory, Group Policy, DNS, DHCP, Failover Clustering.
• Experience with Entra ID, Exchange (Server/Online/Hybrid) and MECM (SCCM) is preferred.
• You can use scripts (e.g. PowerShell, Python) to automate routine administrative tasks.
• Knowledge of networking fundamentals, server hardware and VM deployments.
• 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 DevOps/CI CD and IaC practices, containerization and Kubernetes.
• Prior experience in the trading or financial services industry.

The annual base salary range for this position is $120,000 to $160,000 depending on the candidate’s experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus.

In addition, DRW offers a comprehensive suite of employee benefits including:

• 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

For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at https://drw.com/privacy-notice .