Senior Windows Systems Engineer, Admin

Jobtailor; Phillipsburg (NJ); On-site; USD 120,000 - 180,000; Full time

Job summary

Jobtailor is seeking a senior Windows Server Administrator to lead the administration and ongoing support of Windows Server environments across versions from 2012 R2 to 2025. You will manage the full lifecycle, monitor health and performance, and coordinate upgrades and migrations.

The role requires extensive experience with Active Directory, Entra ID/Azure AD, Microsoft 365, Exchange Online, and Azure. You will mentor junior staff, work with a small team, and ensure security and

Qualifications

• Minimum 10 years of hands-on experience supporting Windows Server environments.
• Advanced experience administering Windows Server across physical and virtual infrastructure.
• Strong experience with Active Directory and Microsoft Entra ID/Azure Active Directory.
• Advanced Microsoft 365 and Exchange/Exchange Online administration experience.
• Strong Microsoft Azure administration experience.
• Hands‑on experience with Group Policy (GPO), DNS, DHCP, Print Servers, and Windows File Systems.
• Experience configuring and administering IIS.
• Experience with SFTP setup and administration.
• Strong virtualization experience, particularly Microsoft Hyper-V.
• Experience administering VMware environments.
• Strong troubleshooting, analytical, and problem‑solving capabilities.
• Ability to manage complex technical issues through resolution.
• Experience providing technical direction or coordinating engineers and administrators.
• Ability to work independently and take ownership of complex technical problems.

Responsibilities

• Administer, maintain, and support Windows Server environments across versions 2012 R2 through 2025.
• Manage the full Windows Server lifecycle, including installation, configuration, upgrades, patching, performance tuning, troubleshooting, and decommissioning.
• Monitor server health, performance, capacity, and availability and proactively address infrastructure issues.
• Plan and execute server upgrades, migrations, maintenance, and infrastructure changes.
• Administer enterprise Active Directory and Microsoft Entra ID/Azure Active Directory.
• Manage users, groups, permissions, organizational units, authentication, Group Policy, DNS, DHCP, file systems, and print servers.
• Administer Microsoft 365, Microsoft Exchange, and Exchange Online.
• Support Microsoft 365 and Exchange users, licensing, permissions, mailboxes, groups, migrations, upgrades, and service-impacting incidents.
• Administer Microsoft Azure environments and support identity, access, security, configuration, and on‑premises integration.
• Administer Microsoft Hyper-V and support VMware environments, including potential VMware-to-Hyper-V migrations.
• Configure, administer, and troubleshoot Microsoft IIS and SFTP environments.
• Participate in infrastructure upgrades, migrations, deployments, and technical projects.
• Apply security, patching, and system‑management standards.
• Provide senior‑level technical support, guidance, and mentoring.
• Coordinate technical activities across a small team when required.
• Prioritize incidents, service requests, maintenance activities, and project requirements.
• Maintain technical documentation, configurations, procedures, and change records.
• Use ServiceNow or other service‑management platforms to manage incidents, requests, changes, and technical work.

Skills

Windows Server Administration

Active Directory Management

Microsoft 365 Administration

Microsoft Azure Administration

Hyper-V

VMware

IIS Configuration

SFTP Administration

Troubleshooting and Problem Solving

Performance Tuning

Technical Documentation

Team Leadership

Ownership of Technical Problems

Education

Bachelor’s degree in Computer Science, Engineering, Information Technology, or related technical field, or equivalent relevant professional experience.

Master’s degree (preferred)

Tools

ServiceNow

Microsoft Entra ID

Exchange Online

VMware

Microsoft Hyper‑V

Job description

• Administer, maintain, and support Windows Server environments across versions 2012 R2 through 2025.


• Manage the full Windows Server lifecycle, including installation, configuration, upgrades, patching, performance tuning, troubleshooting, and decommissioning.


• Monitor server health, performance, capacity, and availability and proactively address infrastructure issues.


• Plan and execute server upgrades, migrations, maintenance, and infrastructure changes.


• Administer enterprise Active Directory and Microsoft Entra ID/Azure Active Directory.


• Manage users, groups, permissions, organizational units, authentication, Group Policy, DNS, DHCP, file systems, and print servers.


• Administer Microsoft 365, Microsoft Exchange, and Exchange Online.


• Support Microsoft 365 and Exchange users, licensing, permissions, mailboxes, groups, migrations, upgrades, and service-impacting incidents.


• Administer Microsoft Azure environments and support identity, access, security, configuration, and on‑premises integration.


• Administer Microsoft Hyper-V and support VMware environments, including potential VMware-to-Hyper-V migrations.


• Configure, administer, and troubleshoot Microsoft IIS and SFTP environments.


• Participate in infrastructure upgrades, migrations, deployments, and technical projects.


• Apply security, patching, and system‑management standards.


• Provide senior‑level technical support, guidance, and mentoring.


• Coordinate technical activities across a small team when required.


• Prioritize incidents, service requests, maintenance activities, and project requirements.


• Maintain technical documentation, configurations, procedures, and change records.


• Use ServiceNow or other service‑management platforms to manage incidents, requests, changes, and technical work.

Requirements

• Minimum 10 years of hands‑on experience supporting Windows Server environments.


• Advanced experience administering Windows Server across physical and virtual infrastructure.


• Strong experience with Active Directory and Microsoft Entra ID/Azure Active Directory.


• Advanced Microsoft 365 and Exchange/Exchange Online administration experience.


• Strong Microsoft Azure administration experience.


• Hands‑on experience with Group Policy (GPO), DNS, DHCP, Print Servers, and Windows File Systems.


• Experience configuring and administering IIS.


• Experience with SFTP setup and administration.


• Strong virtualization experience, particularly Microsoft Hyper-V.


• Experience administering VMware environments.


• Strong troubleshooting, analytical, and problem‑solving capabilities.


• Ability to manage complex technical issues through resolution.


• Experience providing technical direction or coordinating engineers and administrators.


• Ability to work independently and take ownership of complex technical problems.


• Strong written and verbal communication skills.


• Ability to communicate technical issues clearly to technical and non‑technical stakeholders.


• Strong attention to documentation, security, operational standards, and change management.


• Bachelor’s degree in Computer Science, Engineering, Information Technology, or related technical field, or equivalent relevant professional experience.


• Occasional after‑hours responsibilities may be required.


• Master’s degree is preferred, not required.


• ServiceNow, VMware-to-Hyper‑V migration, hybrid Microsoft environment, team leadership, and relevant infrastructure certifications are preferred or assets.

Core Competencies

Demonstrates extensive expertise in administering and supporting Windows Server environments, including advanced skills in Active Directory, Microsoft 365, and Azure administration. Proven ability to manage complex technical issues, provide senior‑level support, and coordinate technical activities within a team.

Highest‑signal resume keywords

• Windows Server Administration


• Active Directory Management


• Microsoft 365 Administration


• Microsoft Azure Administration


• Virtualization with Hyper‑V

ATS Optimization Keywords

Hard Skills

• Windows Server Lifecycle Management


• Group Policy Administration


• DNS Configuration


• DHCP Management


• Print Server Administration


• IIS Configuration


• SFTP Administration


• Troubleshooting and Problem Solving


• Performance Tuning


• Technical Documentation

Soft Skills

• Strong Communication Skills


• Analytical Skills


• Attention to Detail


• Team Leadership


• Ownership of Technical Problems

Certifications & Qualifications

• Infrastructure Certifications


• Relevant Technical Certifications

Industry Keywords

• Hybrid Microsoft Environment


• Technical Direction


• Change Management


• Operational Standards


• Incident Management

Tools & Technologies

• ServiceNow


• Microsoft Entra ID


• Exchange Online


• VMware


• Microsoft Hyper‑V