Windows Server Administrator Jobs
Windows Server Administrator jobs are open across healthcare, finance, government, and enterprise IT, from junior administrator to senior infrastructure engineer, with specializations in Active Directory, virtualization, and cloud hybrid environments. See the openings below and apply to the ones that match your experience.
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Showing 5 of 70+ Windows Server Administrator jobs
Shape the Future of a Modern Hybrid Infrastructure at OCB!
Are you a skilled IT professional with deep expertise in Windows Server, Microsoft 365, and virtualization technologies? Do you thrive in environments where you can own systems end-to-end, implement smart automation, and strengthen security across on-prem and cloud platforms? If so, we want to meet you.
OCB is seeking an experienced Windows & Microsoft 365 Administrator to support, maintain, and enhance our hybrid IT environment. This is a hands-on technical role ideal for someone who loves solving complex problems, optimizing systems, and driving operational excellence. This position will be Monday Through Friday 8-4:30 with the option of up to 2 days hybrid.
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What You’ll Do
As a key member of our infrastructure team, you will:
- Manage and support Windows Server environments (2016/2019/2022/2025) including Active Directory, DNS, DHCP, and GPOs
- Administer core Microsoft 365 services such as Exchange Online, Teams, SharePoint, OneDrive, Azure AD, and Intune
- Support and maintain VMware infrastructure, including ESXi hosts and vCenter
- Monitor system performance, reliability, and availability across both on-prem and cloud ecosystems
- Perform regular updates, patching, and backups—ensuring compliance with security policies
- Use PowerShell to automate routine processes and improve efficiency
- Partner with cross-functional teams to deliver infrastructure upgrades and strategic projects
- Maintain detailed documentation of systems, procedures, and configurations
- Leverage M365 Security & Compliance tools (DLP, Conditional Access, Defender) to strengthen enterprise security posture
- Microsoft 365 administration: Demonstrated experience managing Entra ID, Exchange Online, SharePoint Online, Teams, and Intune in a production environment.
- Identity security: Ability to implement Conditional Access, phishing-resistant MFA, privileged identity management, emergency access accounts, and restrictions on unmanaged devices.
- PowerShell and Microsoft Graph automation: Ability to automate onboarding, offboarding, license management, access reviews, and configuration reporting.
- Microsoft Copilot administration and governance: Hands-on experience deploying and managing Microsoft 365 Copilot, including licensing, permissions, data protection, agent controls, and third-party integrations.
- Application governance: Experience reviewing enterprise applications, OAuth permissions, service principals, and administrative consent to identify and restrict excessive access.
- Data protection and external sharing: Ability to manage sensitivity labels, DLP policies, retention controls, external sharing, and guest access across Microsoft 365.
- Troubleshooting and investigations: Ability to investigate issues using Entra sign-in logs, audit logs, message tracing, and endpoint compliance data, and support security incident response.
- Controlled, documented administration: Commitment to least-privilege access, configuration documentation, change management, and validation before broad deployment.
- Licensing and recovery: Ability to optimize licensing costs and validate recovery procedures for users, mailboxes, and business data, with an understanding of native retention and backup limitations.
-
What You Bring
- 5–8 years of hands-on experience with Windows Server & Microsoft 365 administration
- Strong proficiency with Azure AD and the Microsoft 365 Admin Center
- Solid experience with VMware vSphere, ESXi, and vCenter
- Expertise in AD, Group Policy, DNS, DHCP, and related infrastructure services
- Working knowledge of security best practices for both cloud and on-prem environments
- Strong PowerShell scripting skills
- Excellent troubleshooting abilities and clear communication skills
-
Preferred Skills & Certifications
- Experience with M365 security frameworks including Compliance Center, Threat Management, and Secure Score
- One or more of the following certifications:
o Microsoft 365 Certified: Modern Desktop Administrator Associate
o Microsoft Certified: Security Administrator Associate
o VMware Certified Professional (VCP) or equivalent
-
Education
- Bachelor’s degree in Computer Science, Information Technology, or related field —or equivalent hands-on experience
-
Benefits Offered:
- Health & Dental Insurance- eligible 1st day of employment
- Paid time off and paid holidays
- Health & Dependent Reimbursement Accounts
- 401(k) Plan with company contribution
- Company paid Life and LTD Insurance
- Employee discounts
To find out more about OCB, please visit our website at www.eyeboston.com.
Shape the Future of a Modern Hybrid Infrastructure at OCB!
Are you a skilled IT professional with deep expertise in Windows Server, Microsoft 365, and virtualization technologies? Do you thrive in environments where you can own systems end-to-end, implement smart automation, and strengthen security across on-prem and cloud platforms? If so, we want to meet you.
OCB is seeking an experienced Windows & Microsoft 365 Administrator to support, maintain, and enhance our hybrid IT environment. This is a hands-on technical role ideal for someone who loves solving complex problems, optimizing systems, and driving operational excellence. This position will be Monday Through Friday 8-4:30 with the option of up to 2 days hybrid.
-
What You’ll Do
As a key member of our infrastructure team, you will:
- Manage and support Windows Server environments (2016/2019/2022/2025) including Active Directory, DNS, DHCP, and GPOs
- Administer core Microsoft 365 services such as Exchange Online, Teams, SharePoint, OneDrive, Azure AD, and Intune
- Support and maintain VMware infrastructure, including ESXi hosts and vCenter
- Monitor system performance, reliability, and availability across both on-prem and cloud ecosystems
- Perform regular updates, patching, and backups—ensuring compliance with security policies
- Use PowerShell to automate routine processes and improve efficiency
- Partner with cross-functional teams to deliver infrastructure upgrades and strategic projects
- Maintain detailed documentation of systems, procedures, and configurations
- Leverage M365 Security & Compliance tools (DLP, Conditional Access, Defender) to strengthen enterprise security posture
- Microsoft 365 administration: Demonstrated experience managing Entra ID, Exchange Online, SharePoint Online, Teams, and Intune in a production environment.
- Identity security: Ability to implement Conditional Access, phishing-resistant MFA, privileged identity management, emergency access accounts, and restrictions on unmanaged devices.
- PowerShell and Microsoft Graph automation: Ability to automate onboarding, offboarding, license management, access reviews, and configuration reporting.
- Microsoft Copilot administration and governance: Hands-on experience deploying and managing Microsoft 365 Copilot, including licensing, permissions, data protection, agent controls, and third-party integrations.
- Application governance: Experience reviewing enterprise applications, OAuth permissions, service principals, and administrative consent to identify and restrict excessive access.
- Data protection and external sharing: Ability to manage sensitivity labels, DLP policies, retention controls, external sharing, and guest access across Microsoft 365.
- Troubleshooting and investigations: Ability to investigate issues using Entra sign-in logs, audit logs, message tracing, and endpoint compliance data, and support security incident response.
- Controlled, documented administration: Commitment to least-privilege access, configuration documentation, change management, and validation before broad deployment.
- Licensing and recovery: Ability to optimize licensing costs and validate recovery procedures for users, mailboxes, and business data, with an understanding of native retention and backup limitations.
-
What You Bring
- 5–8 years of hands-on experience with Windows Server & Microsoft 365 administration
- Strong proficiency with Azure AD and the Microsoft 365 Admin Center
- Solid experience with VMware vSphere, ESXi, and vCenter
- Expertise in AD, Group Policy, DNS, DHCP, and related infrastructure services
- Working knowledge of security best practices for both cloud and on-prem environments
- Strong PowerShell scripting skills
- Excellent troubleshooting abilities and clear communication skills
-
Preferred Skills & Certifications
- Experience with M365 security frameworks including Compliance Center, Threat Management, and Secure Score
- One or more of the following certifications:
o Microsoft 365 Certified: Modern Desktop Administrator Associate
o Microsoft Certified: Security Administrator Associate
o VMware Certified Professional (VCP) or equivalent
-
Education
- Bachelor’s degree in Computer Science, Information Technology, or related field —or equivalent hands-on experience
-
Benefits Offered:
- Health & Dental Insurance- eligible 1st day of employment
- Paid time off and paid holidays
- Health & Dependent Reimbursement Accounts
- 401(k) Plan with company contribution
- Company paid Life and LTD Insurance
- Employee discounts
To find out more about OCB, please visit our website at www.eyeboston.com.
Windows Server Administrator Jobs by Experience Level
See All 70 Windows Server Administrator Jobs
Find roles that match your experience and apply in just a few clicks.
Find JobsWindows Server Administrator Job Market
Who's Hiring
Top Industries Hiring
- Banking & Financial Services
What Employers Look For
The qualifications that appear most often in windows server administrator jobs.
- Three or more years administering Windows Server in a production environment
- Hands-on experience with Active Directory, Group Policy, and DNS configuration
- Proficiency in PowerShell scripting for automation and system management tasks
- Experience with virtualization platforms such as VMware vSphere or Microsoft Hyper-V
- Microsoft certifications including MCSA, MCSE, or AZ-800 preferred by most employers
- Familiarity with backup and recovery tools such as Veeam, Acronis, or Windows Server Backup
Tips for Your Windows Server Administrator Job Search
Tailor your resume to each stack
Many windows server administrator postings list a specific combination of Windows Server versions, Hyper-V or VMware, and backup tools. Match your resume's skills section to the exact versions and platforms named in each listing, not just the role title.
Lead with certifications above experience
Hiring managers for windows server administrator roles often filter by MCSA, MCSE, or CompTIA Server+ before reading work history. Put your active certifications in the top third of your resume so they clear automated screening before your job titles are even read.
Apply early to roles that fit
Migrate Mate lists windows server administrator openings from across the United States in one place, so you can find roles that match your stack and apply directly to each listing without jumping between multiple sites.
Target postings that name your tools
Filter openings by the specific technologies you know best, such as Active Directory, Group Policy, PowerShell automation, or Azure AD Connect. Applying where your exact toolset appears in the job description dramatically improves your callback rate.
Prepare for scenario-based technical screens
Windows server administrator interviews frequently include live troubleshooting scenarios: a DNS resolution failure, a Group Policy conflict, or a replication lag. Practice walking through your diagnostic steps out loud so you can narrate your process clearly under pressure.
Negotiate scope before accepting any offer
Before accepting, clarify whether on-call rotation is included, how many servers you'll own, and whether the team runs a ticketing system or informal requests. These details define your actual workload and rarely appear in the job description.
Windows Server Administrator Jobs: Frequently Asked Questions
Which companies are hiring the most windows server administrators?
The companies hiring the most windows server administrators right now include Akina, IPT Associates, and Leidos, with the largest share of openings in Maryland, Virginia, and Ohio, based on current listings on Migrate Mate as of November 2026. Healthcare systems, federal contractors, and large financial institutions consistently post the highest volumes of these roles.
How many windows server administrator jobs are remote?
About 26% of windows server administrator openings are fully remote or hybrid as of November 2026, with the highest remote share in roles focused on cloud-integrated environments and Azure AD or M365 administration. Roles requiring hands-on hardware access, data center presence, or on-site security compliance tend to remain fully on-site.
How do you become a windows server administrator?
Start by building foundational skills in networking, Active Directory, and Windows Server operating systems through lab practice on a home virtualization setup or a cloud trial environment. Earn an entry-level certification such as CompTIA Server+ or the Microsoft AZ-800 exam to validate your skills. Then apply for junior administrator or IT support roles that include server responsibilities, using those positions to build documented production experience.
How do you get hired as a windows server administrator with little experience?
Build a home lab using free Hyper-V or trial licenses to practice configuring Active Directory, DNS, DHCP, and Group Policy, then document that work concretely on your resume. Entry-level help desk or systems support roles that touch server environments are the most common path in. Hiring managers in this field often weigh a CompTIA Server+ or Microsoft certification more heavily than a degree when evaluating candidates with limited work history.
What does the windows server administrator interview process look like?
Most windows server administrator interviews begin with a phone screen covering your experience with specific Windows Server versions and tools. A technical round follows, often including scenario questions on Active Directory troubleshooting, Group Policy conflicts, or DNS failures. Some employers add a live lab exercise or a written assessment. Final rounds typically involve a conversation with an infrastructure manager about team structure, on-call expectations, and your approach to change management.
Where can I find and apply to windows server administrator jobs?
You can find and apply to windows server administrator jobs on Migrate Mate, which lists current openings from across the United States in one place. Search for roles that match your server stack, certifications, and experience level, then apply directly to each listing. New openings are added regularly, so checking back frequently gives you the best chance of catching roles before they close.
See All 70 Windows Server Administrator Jobs
Find roles that match your experience and apply in just a few clicks.
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