Windows 365 Engineer

Role Description: The Windows 365 Engineer is a full-time, on-site role based in Chicago, IL. This role is responsible for designing, configuring, and maintaining Windows 365 environments and related infrastructure to support secure, reliable operations for public safety clients. Day-to-day tasks include managing operating systems, performing system administration, monitoring performance and availability, and resolving technical issues through proactive and reactive troubleshooting. The engineer will collaborate with internal teams and client stakeholders to implement best practices, support deployments and upgrades, and ensure compliance with security and regulatory requirements. This position also involves documenting configurations, maintaining standard operating procedures, and contributing to continuous improvement of SPSG’s managed services offerings.

Qualifications: Strong skills in Windows and related operating systems, including configuration, optimization, and security. Experience with system administration and infrastructure management in enterprise or public sector environments. Proficiency in troubleshooting complex technical issues across endpoints, networks, and cloud-based services. Knowledge of Windows 365, Microsoft 365, and virtualization or cloud technologies (e.g., Azure) is highly beneficial. Understanding of networking fundamentals, identity and access management, and endpoint security best practices. Ability to document technical processes clearly and collaborate effectively with technical and non-technical stakeholders. Prior experience in managed services or consulting environments, ideally supporting public safety or regulated industries, is a plus. Relevant certifications (e.g., Microsoft Certified: Windows Client, Azure Administrator, or similar) and an associate or bachelor’s degree in Information Technology, Computer Science, or related field are preferred.