Senior Systems Engineer (Microsoft)

Location: Chicago, United States

Annual base salary: $175,000–$210,000, plus an annual discretionary bonus.

Company

hirify.global is a diversified trading firm using technology and proprietary capital to operate across global financial markets and alternative investment strategies.

What you will do

• Administer Active Directory, DNS, DHCP, Group Policy, and Exchange across on-premise, online, and hybrid environments.
• Deploy, maintain, and support Windows Server environments from 2016 through 2025.
• Support Entra ID, OneDrive, Copilot, and Microsoft 365 services.
• Configure single sign-on and federation using SAML, OAuth/OIDC, and SCIM.
• Triage operations tickets, respond to critical production incidents, and implement planned and ad hoc changes.
• Document system configurations, create repeatable runbooks, and participate in global on-call support and occasional weekend maintenance.

Requirements

• 5+ years of experience managing Windows Server infrastructure in high-visibility, mission-critical environments.
• Deep expertise in Active Directory, Group Policy, DNS, DHCP, Failover Clustering, and load balancers.
• Hands-on experience with Entra ID, Exchange Server/Online/Hybrid, and MECM/SCCM.
• Proficiency with PowerShell, Python, infrastructure as code such as Terraform or Ansible, and Git-based version control.
• Strong networking knowledge, plus experience with server hardware, hypervisors, and virtual machine deployments.
• Ability to troubleshoot critical issues under pressure, document technical processes, and communicate across teams.

Nice to have

• Experience with Splunk, Grafana, Alertmanager, or Prometheus.
• Familiarity with containerization and Kubernetes.
• Experience in trading or financial services, particularly in low-latency environments.

Culture & Benefits

• Autonomous environment focused on innovation, curiosity, and challenging consensus.
• Global support team with an on-call rotation and occasional weekend maintenance.
• Medical, pharmacy, dental, and vision insurance.
• 401(k) with discretionary employer match, disability and life insurance, HSA, and FSA.