Endpoint System Administrator with Windows Server

Job description

The successful candidate will help ensure systems remain secure, stable, compliant, and current by managing operating system and security updates, testing and deploying patches, troubleshooting deployment failures, coordinating maintenance activities, and maintaining accurate infrastructure documentation.

This role requires experience supporting large enterprise environments and the ability to perform production maintenance while minimizing disruption to business operations. Key ResponsibilitiesEndpoint & Patch ManagementManage enterprise patching and update activities across Windows and macOS endpoints and Windows/Linux server environments.Schedule, test, deploy, and monitor operating system patches, security updates, hotfixes, and feature updates.Configure and maintain centralized endpoint and patch management solutions such as Microsoft Intune, Microsoft SCCM/Configuration Manager, and Microsoft Azure Update Manager.Develop and maintain automated patching policies and deployment schedules.Monitor patch compliance and identify systems that have failed or missed required updates.Troubleshoot deployment failures and remediate problematic endpoints and servers.Support firmware, driver, and BIOS updates across enterprise endpoint devices.Security & Vulnerability RemediationMonitor security and vulnerability management platforms, including Microsoft Defender, for vulnerabilities, critical CVEs, missing patches, and required remediation activities.Prioritize and coordinate remediation of critical and high-risk vulnerabilities.Work with security and infrastructure teams to ensure systems meet organizational security and patch compliance requirements.Validate successful remediation and maintain appropriate evidence and documentation.Server Administration & MaintenanceAdminister and maintain enterprise Windows Server environments, including Windows Server 2016 2022/2025.Support patching, upgrades, configuration changes, and routine maintenance of server infrastructure.Coordinate maintenance windows and perform production upgrades during approved off-hours when required.Monitor server health and investigate system issues related to patches, upgrades, configuration changes, and operating system performance.Develop and execute rollback and recovery procedures when upgrades or patches cause system instability.Testing & Change ManagementEstablish and maintain controlled testing and staging processes for patches and system upgrades.Validate operating system, application, and infrastructure compatibility before production deployment.Conduct post-deployment validation to confirm system stability and successful installation.Document deployment plans, test results, identified issues, rollback procedures, and production outcomes.Coordinate planned changes with technical teams and business stakeholders to minimize operational disruption.Infrastructure Lifecycle ManagementSupport the complete lifecycle of enterprise laptops, workstations, and servers.Maintain accurate hardware and software inventory information.Track operating system versions, firmware levels, patch status, and infrastructure configurations.Identify systems approaching end-of-support or end-of-life and assist with upgrade or replacement planning.Maintain configuration, inventory, maintenance, and patch schedule documentation. Required QualificationsDemonstrated at least 5+ years of experience administering enterprise endpoint and server environments.Proven experience executing enterprise patch deployments and operating system upgrade initiatives across 1,000+ endpoints and multi-server environments.Strong hands-on experience with Microsoft Intune.Strong experience with Microsoft SCCM / Microsoft Configuration Manager or comparable enterprise endpoint management platforms.Strong knowledge of Windows Server 2016, 2019, 2022, and/or 2025 environments.Experience troubleshooting failed patches, software deployments, operating system upgrades, and endpoint configuration issues.Understanding of enterprise vulnerability remediation and security patching processes.Experience developing and executing testing, deployment, rollback, and recovery procedures.Ability to analyze deployment logs and determine root causes of failed updates or system instability.Strong documentation, organizational, and problem-solving skills.Strong written and verbal communication skills with the ability to coordinate technical changes across multiple teams.Ability to support scheduled maintenance activities outside normal business hours when required. Preferred QualificationsExperience with one or more of the following is highly desirable:Microsoft Azure Update ManagerMicrosoft DefenderWindows AutopilotMicrosoft Entra ID / Azure Active DirectoryPowerShell scripting and automationWindows Server administrationLinux server patching and administrationEnterprise vulnerability managementEndpoint security and compliance managementPreferred CertificationsOne or more of the following certifications is preferred but not required:Microsoft Certified: Endpoint Administrator Associate (MD-102)Relevant Microsoft Windows Server / Azure certificationCompTIA Security+CompTIA Server+Other relevant Microsoft, cloud, infrastructure, or cybersecurity certifications Key CompetenciesThe ideal candidate will demonstrate:Strong hands-on troubleshooting and root-cause analysis skillsAbility to manage large-scale patching and upgrade activitiesAttention to detail in security-sensitive production environmentsStrong ownership and follow-throughAbility to prioritize critical vulnerabilities and operational issuesEffective communication with infrastructure, security, application, and business teamsAbility to document technical work clearly and maintain accurate operational recordsAbility to work independently while collaborating effectively within a technical team What Success Looks LikeSuccess in this role means maintaining a secure, reliable, and well-managed endpoint and server environment with:High patch and update complianceTimely remediation of critical vulnerabilitiesMinimal disruption from production upgradesEffective testing and rollback proceduresAccurate infrastructure and lifecycle documentationRapid identification and resolution of failed deploymentsProactive management of systems approaching end-of-life or requiring upgrades