Senior Systems Engineer - Microsoft
- Pay
- $155,000 – $185,000 per year
- Location
- Chicago, IL · Hybrid
- Job type
- Full-time
- Level
- Senior
- Experience
- 5+ years
- Listed
- 30 days ago
Skills & highlights for this role
- Active Directory
- Group Policy
- Exchange Server
- PowerShell
- Entra ID
Also useful
- Splunk
- Grafana
- Kubernetes
- Terraform
- Ansible
Stated benefits & perks
- Group medical
- Dental
- Vision
- 401k match
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.
Pay and benefits
The annual base salary range for this position is $155,000 to $185,000 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, and flexible spending accounts.
About DRW
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.
From DRW's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.
How Rolev.ai helps with this application
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Common questions
What is the salary for the Senior Systems Engineer - Microsoft role at DRW?
The Senior Systems Engineer - Microsoft posting at DRW states compensation of $155,000 – $185,000 per year. It is listed as a full-time position. Final pay may depend on location, experience, and interview evaluation on DRW's official career site.
Where is the Senior Systems Engineer - Microsoft job at DRW located?
This Senior Systems Engineer - Microsoft position at DRW is located in Chicago, IL (Hybrid). Always check DRW's application page for specific state eligibility or relocation policies.
What qualifications are required for Senior Systems Engineer - Microsoft at DRW?
For the Senior Systems Engineer - Microsoft role, DRW highlights 5+ years of relevant experience; experience with Active Directory, Group Policy, Exchange Server, PowerShell, Entra ID. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.
How do I apply for the Senior Systems Engineer - Microsoft position at DRW?
This listing links directly to DRW's Greenhouse application page. You can apply directly on DRW's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Greenhouse application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.