Senior Systems Engineer - Microsoft DRW plus annual discretionary

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 trade 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, and Exchange (on-premise, Online, and hybrid).
• Deploy, maintain, and support Windows Server environments (2016–2025).
• Support Microsoft cloud services, including Entra , One Drive, Copilot, and Microsoft 365 services.
• Configure single sign-on and federation using SAML, OAuth/OIDC, and SCIM.
• Triage and resolve tickets from the operations queue and 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 an 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, and load balancers.
• Hands-on experience with Entra , Exchange (Server, Online, and Hybrid), and MECM (SCCM).
• Proficiency with scripting (Power Shell and Python), infrastructure as code such as Terraform and Ansible, and version control systems including Git Hub, Git Lab, and Bitbucket.
• Strong networking knowledge and experience with server hardware and hypervisor/VM deployments.
• Excellent documentation and knowledge management skills, with the ability to turn ad hoc tasks into documented, repeatable processes.
• Proven ability to troubleshoot and resolve critical issues under pressure; trading or low-latency environment experience is a plus.
• Strong written and verbal communication skills, including the ability to work across teams and have evidence-based discussions on technical and operational topics.
• Eagerness to learn, collaborate, and find solutions under interesting constraints.

Bonus points if you have:

• Experience with Splunk, Grafana, Alert manager, and Prometheus.
• Familiarity with containerization and Kubernetes.
• Prior experience in the trading or financial services industry.

Compensation and benefits:

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. DRW offers a comprehensive suite of employee benefits, including group medical, pharmacy, dental, and vision insurance; a 401(k) with discretionary employer match; short- and long-term disability; life and AD&D insurance;

health savings accounts; and flexible spending accounts.