Senior Systems Engineer - Microsoft
DRW is a Chicago-based diversified trading firm that uses technology, quantitative research, and risk management to provide liquidity across traditional and digital-asset markets.
About DRW
Founded by Don Wilson in 1992, DRW trades for its own account across global markets and operates strategies in cryptoassets, venture capital, real estate, carbon markets, and public-equity investments. Its crypto business, Cumberland, has provided institutional crypto-asset liquidity since 2014.
Skills
Candidate Availability
Required and preferred rules are kept separate and reflect the wording in the original posting.
About the Role
You will administer core Microsoft services and deploy, maintain, and support Windows Server environments. You will support cloud services, configure identity integrations, resolve operational tickets and critical incidents, implement changes, and maintain system documentation and runbooks. You will participate in on-call support and occasional weekend maintenance.
Requirements
- 5+ years managing Windows Server infrastructure in mission-critical environments
- Expertise in Active Directory, Group Policy, DNS, DHCP, Failover Clustering, and load balancers
- Experience with Entra ID, Exchange, and MECM
- Scripting with PowerShell and Python
- Infrastructure as code with Terraform and Ansible
- Version control experience
- Networking, server hardware, and hypervisor or virtual machine deployment knowledge
- Documentation and knowledge management skills
- Troubleshooting and critical-incident resolution skills
- Written and verbal communication skills
Responsibilities
- Administer Active Directory, DNS, DHCP, Group Policy, and Exchange
- Deploy, maintain, and support Windows Server environments
- Support Entra ID, OneDrive, Copilot, and Microsoft 365 services
- Configure single sign-on and federation
- Triage and resolve operational tickets and critical production incidents
- Implement planned and ad hoc changes through change management processes
- Maintain system documentation and repeatable runbooks
- Participate in on-call support and occasional weekend maintenance
Benefits
- Annual discretionary bonus
- Medical, pharmacy, dental, and vision insurance
- 401k with discretionary employer match
- Short- and long-term disability insurance
- Life and AD&D insurance
- Health savings accounts
- Flexible spending accounts