Windows Administrator Jobs
Windows Administrator jobs are open across healthcare, finance, government, and enterprise IT, at every level from junior support to senior and lead, with specializations in Active Directory, Group Policy, and cloud-hybrid environments. Scan the live roles below and apply to whichever ones fit.
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Showing 5 of 70+ Windows 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 Administrator Jobs by Experience Level
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Find Windows Administrator JobsWindows Administrator Job Market
Who's Hiring
Top Industries Hiring
- Banking & Financial Services
What Employers Look For
The qualifications that appear most often in windows administrator jobs.
- Hands-on experience managing Active Directory, DNS, DHCP, and Group Policy in a Windows Server environment
- Proficiency with PowerShell scripting for automation, reporting, and system administration tasks
- Experience with patch management tools such as WSUS, SCCM, or equivalent enterprise update solutions
- Relevant Microsoft certification such as MD-102, AZ-800, or equivalent Windows Server credential
- Familiarity with virtualization platforms including VMware vSphere or Microsoft Hyper-V
- Associate or bachelor's degree in information technology, computer science, or a related field
Tips for Your Windows Administrator Job Search
Tailor your resume for AD depth
Hiring managers for windows administrator roles scan for Active Directory specifics: group policy objects, OU structures, and trust relationships. List those explicitly rather than writing 'managed AD,' which tells them nothing about the scope of what you actually did.
Get your certifications in the right order
Windows administrator postings almost always require at least one Microsoft credential, but which one depends on the stack. Check whether the job targets on-premises Server environments or hybrid Azure setups, then match your MCSA, MD-102, or AZ-800 accordingly before you apply.
Apply early to roles that fit
Migrate Mate lists windows administrator openings from across the United States in one place, so you can find roles that match and apply directly to each listing.
Target postings by infrastructure scale
A windows administrator role at a 50-person company means generalist duties, while an enterprise posting may focus entirely on patch management or PowerShell automation. Filter openings by team size or industry so your experience maps cleanly to what they actually need.
Prep for the technical screen with real scenarios
Interviewers for windows administrator roles frequently give live scenarios: a GPO is not applying, a server is unreachable, a user account is locked in a loop. Walk through your actual troubleshooting steps out loud rather than reciting definitions from documentation.
Negotiate by scoping the environment first
Before accepting an offer, ask about the number of servers managed, backup tools in use, and on-call rotation frequency. Those details reveal workload and risk, and they give you concrete ground to negotiate compensation beyond the base salary figure.
Windows Administrator Jobs: Frequently Asked Questions
Which companies are hiring the most windows administrators?
The most active employers for windows administrators right now are Akina, IPT Associates, and Leidos, and the most openings are in Maryland, Virginia, and Ohio, based on current listings on Migrate Mate as of November 2026. Healthcare systems, defense contractors, and large financial institutions tend to post the most consistently throughout the year.
How many windows administrator jobs are remote?
About 26% of windows administrator openings are fully remote or hybrid as of November 2026, though fully on-site roles remain common because many environments require hands-on hardware access. Cloud-focused sub-roles dealing with Azure Active Directory and Intune device management are the most likely to be posted as fully remote.
How do you become a windows administrator?
Start by building a foundation in Windows Server fundamentals, Active Directory, and networking basics through a degree, a community college program, or self-study. Earn an entry-level Microsoft certification to validate your skills, then gain hands-on exposure through a helpdesk or IT support role. From there, move into a junior sysadmin position, progressively taking ownership of server management and automation tasks until you qualify for a full windows administrator title.
Can you get a windows administrator job with little experience?
Yes, entry-level windows administrator roles do exist, but they typically expect some hands-on exposure, even if informal. Build a home lab running Windows Server, practice configuring Active Directory and Group Policy, and earn a foundational Microsoft certification. Helpdesk experience where you touched server-side tools is a strong bridge, since it shows you can handle escalation and understand the environment.
What does the windows administrator interview process look like?
Most hiring processes for windows administrator roles include an initial phone or video screen focused on your background, followed by a technical interview where you work through real scenarios like troubleshooting a failed GPO or diagnosing a replication issue. Some employers add a practical assessment or ask you to walk through a past project. Final rounds typically involve a conversation with a team lead or IT manager about day-to-day responsibilities and environment specifics.
Where can I find and apply to windows administrator jobs?
You can find and apply to windows administrator jobs on Migrate Mate, which lists current openings from across the United States. Search the available roles, find the ones that match your experience and target environment, and apply directly to each listing that fits.
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