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Remote Windows Administrator Jobs in Ontario (NOW HIRING)

Targeted Talent

Senior Systems Administrator

Hamilton, ON · Remote

$90K - $95K/yr

We are looking for an experienced Senior Systems Administrator (Windows) for our client. This is a permanent position, remote in Ontario! Our client is a large fintech firm with a product that you've ...

Targeted Talent

Senior Systems Administrator

Oshawa, ON · Remote

$90K - $95K/yr

We are looking for an experienced Senior Systems Administrator (Windows) for our client. This is a permanent position, remote in Ontario! Our client is a large fintech firm with a product that you've ...

Targeted Talent

Senior Systems Administrator

Guelph, ON · Remote

$90K - $95K/yr

We are looking for an experienced Senior Systems Administrator (Windows) for our client. This is a permanent position, remote in Ontario! Our client is a large fintech firm with a product that you've ...

Targeted Talent

Senior Systems Administrator

Kitchener, ON · Remote

$90K - $95K/yr

We are looking for an experienced Senior Systems Administrator (Windows) for our client. This is a permanent position, remote in Ontario! Our client is a large fintech firm with a product that you've ...

Targeted Talent

Senior Systems Administrator

Kitchener, ON · Remote

$90K - $95K/yr

We are looking for an experienced Senior Systems Administrator (Windows) for our client. This is a permanent position, remote in Ontario! Our client is a large fintech firm with a product that you've ...

Targeted Talent

Senior Systems Administrator

Hamilton, ON · Remote

$90K - $95K/yr

We are looking for an experienced Senior Systems Administrator (Windows) for our client. This is a permanent position, remote in Ontario! Our client is a large fintech firm with a product that you've ...

Targeted Talent

Senior Systems Administrator

Oshawa, ON · Remote

$90K - $95K/yr

We are looking for an experienced Senior Systems Administrator (Windows) for our client. This is a permanent position, remote in Ontario! Our client is a large fintech firm with a product that you've ...

Targeted Talent

Senior Systems Administrator

Guelph, ON · Remote

$90K - $95K/yr

We are looking for an experienced Senior Systems Administrator (Windows) for our client. This is a permanent position, remote in Ontario! Our client is a large fintech firm with a product that you've ...

World Renew

Systems Administrator

Burlington, ON · On-site +1

CA$82K - CA$92K/yr

Experience providing support to remote teams in low-connectivity environments. * Salesforce ... Administrator Certification (preferred). * Additional IT certifications (e.g., Microsoft, CompTIA ...

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All JobsWindows Administrator JobsRemote Windows Administrator JobsRemote Windows Administrator Jobs in Ontario

Remote Windows Administrator information

See Ontario salary details

$13

$43

$69

How much do remote windows administrator jobs pay per hour?

As of Aug 26, 2026, the average hourly pay for remote windows administrator in Ontario is $43.38, according to ZipRecruiter salary data. Most workers in this role earn between $34.13 and $52.88 per hour, depending on experience, location, and employer.

What is a remote Windows administrator?

Remote Windows Administrators are IT professionals who manage and maintain Windows-based servers, desktops, and networks from a remote location. Their responsibilities include installing and configuring Windows operating systems, troubleshooting technical issues, performing system updates, and ensuring security policies are enforced. They use remote management tools to monitor system performance, apply patches, and resolve user problems without being physically present at the office or data center. This role is essential for organizations that operate distributed environments or have a need for offsite IT support.

What does a remote Windows administrator do?

The job duties of a remote Windows administrator involve working on the customization, configuration, maintenance, and updates of a Windows computer system. Your responsibilities in this work from home position involve performing updates and providing support for the company and organization that uses the Windows system, software, and apps that you install. You take steps to monitor the Windows network from your remote location and troubleshoot when problems arise. As an administrator, you often train staff to use Windows software and also communicate with vendors to ensure that your network has the latest software, cybersecurity, and compatibility updates.

What are the key skills and qualifications needed to thrive as a remote Windows administrator, and why are they important?

To thrive as a Remote Windows Administrator, you need a solid understanding of Windows Server operating systems, network protocols, and system security, typically backed by a degree in IT or relevant certifications like Microsoft Certified: Windows Server Fundamentals. Familiarity with remote management tools (such as Remote Desktop Services, PowerShell, and Active Directory) and ticketing systems is crucial for day-to-day operations. Strong problem-solving abilities, communication skills, and the ability to work independently help distinguish top professionals in this role. These skills ensure effective system administration, rapid issue resolution, and secure, reliable IT environments even when working remotely.

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

Remote Windows Administrators often encounter challenges such as troubleshooting issues without physical access to the hardware, managing security updates across distributed systems, and coordinating with on-site staff for tasks that require hands-on intervention. Effective communication, leveraging remote management tools, and maintaining clear documentation are key strategies to address these challenges. Regular training on new remote technologies and cybersecurity best practices also helps ensure smooth system administration and reduces downtime.

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

AspectRemote Windows AdministratorRemote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, Active Directory, and system updatesManaging network infrastructure, routers, switches, and firewalls
Industry UsageIT support, data centers, enterprise environmentsNetwork service providers, large organizations, IT departments
Common Search/ComparisonYesYes

The Remote Windows Administrator primarily focuses on managing Windows-based servers, Active Directory, and system configurations, while the Remote Network Administrator handles network infrastructure, including routers, switches, and firewalls. Both roles require similar certifications and are essential in IT environments, but they specialize in different aspects of IT infrastructure management.

More about Remote Windows Administrator jobs

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

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

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

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

What cities in Ontario are hiring for Remote Windows Administrator jobs?

Cities in Ontario with the most Remote Windows Administrator job openings:

Remote Windows Administrator jobs near you
Infographic showing various Remote Windows Administrator job openings in Ontario as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 17% Part Time, and 8% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $90,229 per year, or $43.4 per hour.

Senior Systems Administrator

Hamilton, ON • Remote

Targeted Talent
Recruiting and Staffing Services • 11 - 50 employees
Learn more about Targeted Talentexternal

$90K - $95K/yr

Full-time

Medical, Dental

Re-posted 21 days ago

Job description

We are looking for an experienced Senior Systems Administrator (Windows) for our client. This is a permanent position, remote in Ontario! Our client is a large fintech firm with a product that you've likely used many times before.
You'll have the opportunity to work on an extremely large, internationally used payment platform. Your role will encompass managing, building, planning administrating and maintaining infrastructure services like Systems, Containers, Servers, Data Centers and Storage to ensure our client has a robust, scalable and stable infrastructure.

You Have:

  • 7+ years experience working as a Systems Administrator, with extensive experience working with Windows Servers
  • Extensive experience building/automating/administration/monitoring Windows Servers
  • 3+ years of experience working with:
    Windows clustering, SCCM and Active Directory
    Managing servers on a Cloud Platform (Azure)
  • Experience with scripting, automation, and orchestration technologies and languages like batch, PowerShell, VBScript, Perl, Python and SCCM
  • A B.Sc. or equivalent work experience required.

Some AWESOME selling points:

  • Remote + flexible work schedule
  • Competitive salary + Extended Health and Dental Benefits
  • Amazing opportunity for career progression to lead
  • Amazing mentorship (seriously)
  • Plenty of vacay

It's a seriously awesome opportunity! If this looks interesting to you, please click the link and apply.
** Unfortunately we are only able to consider candidates who either live in Canada, or currently have an active Canadian work visa or citizenship for this role.

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About Targeted Talent

Sourced by ZipRecruiter

Your single source for HR professional services, we offer job seekers specialized employment services, spanning contract, permanent positions, and project solutions for highly specialized and managerial level talent needs. Our team of specialized recruiters and consultants abilities extend far beyond resume or career counseling. With hundreds of collaborators strategically located throughout the country, our organization possess the local market knowledge and industry relationships that make successful geography-specific reach possible.

Industry

Recruiting and staffing services

Company size

11 - 50 Employees

Headquarters location

Vancouver, BC, CA

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