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Remote Windows System Administrator Jobs in Massachusetts

Performix

System Administrator

Boston, MA · Remote

While this position is primarily remote, you will serve our Boston\-based team and must live within ... Provision, image, and ship laptops (Windows\/Mac) and peripherals for onboarding employees ...

New

CarGurus

Systems Administrator II

Boston, MA · Remote

... System Administrator II, you will help support and improve the core systems and services our employees use every day. You will work across identity, collaboration tools, office networking, and remote ...

Dungarvin

Information Security Administrator

Boston, MA · On-site +1

Remote (Please note, we are unable to hire candidates located in Pennsylvania or New York.) * Team ... Administer user access across enterprise systems by maintaining accurate permissions, managing ...

New

Professional Moving & Storage

Office Administrator

Boston, MA · On-site +1

$19.50 - $27/hr

... Windows 8 system or higher • Ability to be resourceful and proactive in dealing with issues that may arise • Ability to be flexible, organize, multitask, prioritize and work under pressure ...

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All JobsWindows System Administrator JobsRemote Windows System Administrator JobsRemote Windows System Administrator Jobs in Massachusetts

Remote Windows System Administrator information

See Massachusetts salary details

$59K

$104.8K

$142.5K

How much do remote windows system administrator jobs pay per year?

As of Aug 28, 2026, the average yearly pay for remote windows system administrator in Massachusetts is $104,797.00, according to ZipRecruiter salary data. Most workers in this role earn between $86,300.00 and $120,700.00 per year, depending on experience, location, and employer.

What is a remote Windows system administrator?

A Remote Windows System Administrator is an IT professional responsible for managing, configuring, and maintaining Windows-based servers and systems from a remote location. Their duties include monitoring system performance, applying updates and patches, troubleshooting technical issues, and ensuring the security and reliability of Windows environments across an organization. They often use remote access tools to perform their tasks, helping organizations maintain efficient and secure IT operations without being physically present on-site.

What are the key skills and qualifications needed to thrive as a remote Windows system administrator?

To thrive as a Remote Windows System Administrator, you need expertise in Windows Server administration, Active Directory, network protocols, and typically a degree in IT or related certifications like Microsoft Certified: Windows Server or Azure Administrator. Familiarity with tools such as PowerShell, Remote Desktop Services, VMware, and monitoring platforms is essential for managing and troubleshooting systems remotely. Excellent problem-solving, communication, and time-management skills help you to efficiently address issues and collaborate with distributed teams. These competencies ensure system reliability, security, and fast resolution of technical challenges in a remote environment.

What are some common challenges faced by remote Windows system administrators and how can they be addressed?

Remote Windows System Administrators often face challenges such as ensuring secure remote access, coordinating with geographically dispersed teams, and promptly resolving issues without on-site presence. To address these, effective communication tools, robust security protocols (like VPNs and multi-factor authentication), and proactive monitoring solutions are essential. Building strong documentation practices and maintaining regular updates with team members can also help manage tasks efficiently and ensure smooth operations.

What is the difference between Remote Windows System Administrator vs Remote Network Administrator?

AspectRemote Windows System AdministratorRemote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, Active Directory, and server infrastructureManaging network hardware, routers, switches, and network security
Employer & Industry UsageIT departments across various industries focusing on Windows environmentsOrganizations needing network infrastructure management across industries

Remote Windows System Administrators primarily focus on managing Windows server environments, Active Directory, and related infrastructure. In contrast, Remote Network Administrators concentrate on network hardware, routing, switching, and network security. While both roles require networking certifications like CompTIA Network+ or Cisco CCNA, their daily tasks and focus areas differ significantly, catering to different aspects of IT infrastructure management.

What are the most commonly searched types of Windows System Administrator jobs in Massachusetts?

The most popular types of Windows System Administrator jobs in Massachusetts are:

What are popular job titles related to Remote Windows System Administrator jobs in Massachusetts?

For Remote Windows System Administrator jobs in Massachusetts, the most frequently searched job titles are:

What job categories do people searching Remote Windows System Administrator jobs in Massachusetts look for?

The top searched job categories for Remote Windows System Administrator jobs in Massachusetts are:

What cities in Massachusetts are hiring for Remote Windows System Administrator jobs?

Cities in Massachusetts with the most Remote Windows System Administrator job openings:

Remote Windows System Administrator jobs near you
Infographic showing various Remote Windows System Administrator job openings in Massachusetts as of August 2026, with employment types broken down into 1% As Needed, 79% Full Time, 15% Part Time, 1% Temporary, 3% Contract, and 1% Nights. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $104,797 per year, or $50.4 per hour.

System Administrator

Boston, MA • Remote

Performix
See more jobs at Performixexternal

Contractor

Posted 3 days ago

New

Job description

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Job Overview<\/span><\/span><\/b>
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        <\/span><\/span><\/span><\/span><\/span>We are seeking a skilled and proactive Helpdesk Specialist \/ Junior Systems Administrator for a 3\-month contract.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>In this dual\-focus role, you will provide top\-tier end\-user support while handling foundational systems administration tasks, with a heavy emphasis on Microsoft 365 environments.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>While this position is primarily remote, you will serve our Boston\-based team and must live within 30 minutes of Boston to assist with occasional hands\-on hardware deployments, equipment imaging, or urgent on\-site troubleshooting.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Will need to be able to reach office in 30 minutes to support any tech emergencies if needed.<\/span><\/span><\/span>
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Key Responsibilities:<\/span><\/span><\/b>
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        <\/span><\/span><\/span><\/span><\/span>End\-User Support & Helpdesk<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Serve as the primary point of contact for remote and local employees experiencing technical issues (hardware, software, network, and access).<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Diagnose, troubleshoot, and resolve Tier 1 and Tier 2 helpdesk tickets with a high level of customer service and responsiveness.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Provision, image, and ship laptops (Windows\/Mac) and peripherals for onboarding employees; coordinate the return of equipment for offboarding.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Junior Systems Administration & M365<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Handle end\-to\-end Microsoft 365 (Office 365) setups, including creating user accounts, configuring mailboxes, assigning licenses, and setting up distribution groups\/shared mailboxes.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Manage user permissions and access control via Microsoft Entra ID (formerly Azure Active Directory) and\/or local Active Directory.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Configure and troubleshoot M365 applications (Teams, SharePoint, OneDrive, Outlook) for end\-users.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Assist with basic network troubleshooting (VPN connectivity, Wi\-Fi, home internet configurations for remote workers).<\/span><\/span>
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Required Experience:<\/span><\/span><\/b>
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        <\/span><\/span><\/span><\/span><\/span>2+ years of experience in an IT Helpdesk, Technical Support, or Junior SysAdmin role.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Strong M365 Experience: Proven track record of configuring Office 365 accounts, provisioning mailboxes, and managing basic tenant settings.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Proficient with Active Directory \/ Microsoft Entra ID user administration.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Strong troubleshooting skills across Windows 10\/11 and macOS environments.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Experience utilizing MDM tools (e.g., Intune, Jamf) for device deployment is a major plus.<\/span><\/span>
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Location & Contract Requirements:<\/span><\/span><\/span><\/b>
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        <\/span><\/span><\/span><\/span><\/span>Must be physically located within a 30\-minute radius of Boston, MA.<\/span><\/span>
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        <\/span><\/span><\/span><\/span><\/span>Must have a reliable home internet connection and a dedicated quiet workspace.<\/span><\/span>
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