Endpoint System Administrator with Windows Server
Contract W2
Contract Independent
On-site
Depends on Experience
Triwave Solutions Inc
Fitment
Dice Job Match Score™
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Job Details
Skills
- Management
- Firmware
- Inventory
- Laptop
- Lifecycle Management
- Linux
- Microsoft
- Configuration Management
- Conflict Resolution
- Cyber Security
- Documentation
- Microsoft Azure
- BIOS
- Business Operations
- Communication
- CompTIA
- Root Cause Analysis
- Patch Management
- ROOT
- Recovery
- Regulatory Compliance
- Scripting
- Microsoft Windows
- Microsoft Windows Server
- Operating Systems
- Problem Solving
- Computer Hardware
- IaaS
- Microsoft Operating Systems
- Microsoft SCCM
- Vulnerability Management
- OS X
- Security+
- Server Administration
- Server+
- Servers
- Testing
Summary
System Administrator (Endpoint) - Baltimore, MD(Onsite) - Onsite interview mandatory
Position Overview
We are seeking an experienced Systems Administrator Endpoint & Server Infrastructure to support enterprise endpoint and server environments. This position is ideal for a hands-on systems administrator with strong experience managing Windows environments, enterprise patching, system upgrades, vulnerability remediation, and endpoint management technologies.
The Systems Administrator will be responsible for the ongoing administration, maintenance, patching, upgrading, and lifecycle management of enterprise laptops, workstations, and server infrastructure.
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.
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 Responsibilities
Endpoint & Patch Management
- Manage 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 Remediation
- Monitor 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 & Maintenance
- Administer 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 Management
- Establish 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 Management
- Support 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 Qualifications
- Demonstrated 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 Qualifications
- Experience with one or more of the following is highly desirable:
- Microsoft Azure Update Manager
- Microsoft Defender
- Windows Autopilot
- Microsoft Entra ID / Azure Active Directory
- PowerShell scripting and automation
- Windows Server administration
- Linux server patching and administration
- Enterprise vulnerability management
- Endpoint security and compliance management
Preferred Certifications
- One or more of the following certifications is preferred but not required:
- Microsoft Certified: Endpoint Administrator Associate (MD-102)
- Relevant Microsoft Windows Server / Azure certification
- CompTIA Security+
- CompTIA Server+
- Other relevant Microsoft, cloud, infrastructure, or cybersecurity certifications
Key Competencies
- The ideal candidate will demonstrate:
- Strong hands-on troubleshooting and root-cause analysis skills
- Ability to manage large-scale patching and upgrade activities
- Attention to detail in security-sensitive production environments
- Strong ownership and follow-through
- Ability to prioritize critical vulnerabilities and operational issues
- Effective communication with infrastructure, security, application, and business teams
- Ability to document technical work clearly and maintain accurate operational records
- Ability to work independently while collaborating effectively within a technical team
What Success Looks Like
- Success in this role means maintaining a secure, reliable, and well-managed endpoint and server environment with:
- High patch and update compliance
- Timely remediation of critical vulnerabilities
- Minimal disruption from production upgrades
- Effective testing and rollback procedures
- Accurate infrastructure and lifecycle documentation
- Rapid identification and resolution of failed deployments
- Proactive management of systems approaching end-of-life or requiring upgrades
Employers have access to artificial intelligence language tools (“AI”) that help generate and enhance job descriptions and AI may have been used to create this description. The position description has been reviewed for accuracy and Dice believes it to correctly reflect the job opportunity.
- Dice Id: 91125814
- Position Id: 9062956
- Posted 1 day ago
Company Info
Garnering Accolades for Health and Human Services in Maryland
Based in Columbia, Maryland, Triwave is a Certified Small Business as designated by the Federal government, demonstrating its commitment to contributing to the community and promoting the safety, security, and well-being of citizens. Triwave specializes in innovative services and solutions utilizing cloud, analytics, artificial intelligence, and data management that enhance governance while reducing costs for state and local agencies such as the Department of Human Services (DHS) at Maryland and Department of Child Services (DCS) at Indiana. Triwave recently delivered agency-wide modernization programs for the State of Maryland as a Master Contractor that transformed the technology landscape and garnered award and recognition for the team. Triwave has also received the prestigious honor of being named a top IT Consulting Firm for the years 2022 and 2023.
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