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Remote Weekend System Administrator Jobs in Toronto, ON

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 ...

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 ...

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 ...

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 ...

Morson Talent

25-033 Service Now Developer

Toronto, ON · Remote

$80 - $90/hr

... remote) Job Overview We are seeking a skilled ServiceNow Developer to join our dynamic team. The ... ServiceNow certifications (e.g., Certified System Administrator, Certified Application Developer ...

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All JobsSystem Administrator JobsRemote Weekend System Administrator JobsRemote Weekend System Administrator Jobs in Toronto, ON

Remote Weekend System Administrator information

See Toronto, ON salary details

$21.5K

$66.2K

$131.7K

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

As of Aug 2, 2026, the average yearly pay for remote weekend system administrator in Toronto, ON is $66,233.00, according to ZipRecruiter salary data. Most workers in this role earn between $37,696.00 and $85,890.00 per year, depending on experience, location, and employer.

What are remote weekend system administrators?

Remote weekend system administrators are IT professionals who manage and maintain computer systems, servers, and networks from a remote location during weekends. Their responsibilities include monitoring system performance, troubleshooting technical issues, applying updates or patches, and ensuring system security and availability outside of regular business hours. This role is essential for organizations that require continuous IT support and minimal downtime, even on weekends. Working remotely allows these administrators to provide support from any location with internet access.

What are some unique challenges faced by Remote Weekend System Administrators, and how can they be addressed?

Remote Weekend System Administrators often encounter challenges such as resolving urgent technical issues with limited immediate support, maintaining communication with off-duty team members, and ensuring system stability during lower-staffed hours. To address these challenges, it's important to be proactive in monitoring systems, utilize clear documentation, and establish escalation procedures for critical incidents. Building strong asynchronous communication habits and leveraging collaboration tools can also help ensure smooth operations despite the remote and weekend setting.

What is the difference between Remote Weekend System Administrator vs Remote Weekend Network Technician?

AspectRemote Weekend System AdministratorRemote Weekend Network Technician
Required CertificationsCompTIA Server+, Microsoft Certified: Windows Server FundamentalsCompTIA Network+, Cisco CCNA
Work EnvironmentManaging servers, systems, and infrastructure remotely during weekendsMonitoring and troubleshooting network issues remotely on weekends
Employer & Industry UsageIT companies, data centers, managed service providersTelecommunications, internet service providers, enterprise networks

The Remote Weekend System Administrator primarily manages servers and IT infrastructure remotely during weekends, focusing on system stability and updates. In contrast, the Remote Weekend Network Technician concentrates on troubleshooting and maintaining network connectivity issues remotely. Both roles require similar certifications and often serve the same industries, but their core responsibilities differ in scope—system management versus network troubleshooting.

What are the key skills and qualifications needed to thrive as a Remote Weekend System Administrator, and why are they important?

To thrive as a Remote Weekend System Administrator, you need in-depth knowledge of system administration, networking, and troubleshooting, typically backed by a degree in computer science or related field and relevant experience. Familiarity with operating systems (Windows, Linux), remote management tools, virtualization platforms, and certifications like CompTIA Server+ or Microsoft Certified: Windows Server are highly valued. Excellent problem-solving, time management, and clear communication skills set top candidates apart, as does the ability to work independently during off-hours. These skills and qualities are crucial for ensuring system stability, rapid issue resolution, and reliable support outside of standard business hours.
What are popular job titles related to Remote Weekend System Administrator jobs in Toronto, ON? For Remote Weekend System Administrator jobs in Toronto, ON, the most frequently searched job titles are:
What job categories do people searching Remote Weekend System Administrator jobs in Toronto, ON look for? The top searched job categories for Remote Weekend System Administrator jobs in Toronto, ON are:
Remote Weekend System Administrator jobs near you

Sr. System Administrator, Data Centers

Dialpad

Toronto, ON • On-site, Remote

Full-time

Posted 21 days ago

Job description

About Dialpad
Dialpad is the AI platform for customer experience, built to resolve customer problems in real time across voice and digital. Our AI agents learn from your best human agents and improve with every interaction, helping organizations understand their customers, deliver better experiences, increase operational efficiencies, and build a lasting competitive advantage.

Unlike legacy systems built to route and answer, or standalone agentic bot vendors built to deflect, Dialpad was built to resolve. Our AI agents and human agents operate on a single platform with shared context, allowing Agentic AI to resolve issues, advance deals, and eliminate busywork through automation while seamlessly handing conversations to humans when needed, with full context preserved.

Market-leading brands, including Randstad, Motorola Solutions, Netflix, the San Diego Padres, the Colorado Rockies Baseball Club, and Cal Athletics, trust Dialpad. Dialpad is backed by Andreessen Horowitz, GV, ICONIQ Capital, and T-Mobile.

Being a Dialer
At Dialpad, AI isn't just a feature; it's how our teams do their best work every day. We put powerful AI tools in every employee's hands so they can move faster, think bigger, and achieve more.

We believe every conversation matters. And we've built the platform that turns those conversations into insight and action, for our customers and ourselves.

We look for people who are intensely curious and hold themselves to a high bar. Our ambition is significant, and achieving it requires a team that operates at the highest level. We seek individuals who embody our core traits: Scrappy, Curious, Optimistic, Persistent, and Empathetic.

Your role
As a Sr. System Administrator on the Data Centers team, you'll own both our hardware and cloud infrastructures, with a particular focus on reliability, scalability, and operational excellence. You'll manage the administration and lifecycle of our global server fleet and lead key initiatives in automation, observability, and performance.

You'll also take the lead on capacity planning, including physical data center needs, and will be a technical partner to stakeholders across Engineering as we evolve our infrastructure footprint. In addition, you'll evaluate, propose, and implement new project initiatives such as intrusion detection/prevention, system/security hardening, and automating manual processes.

This position reports to our Engineering Manager, Data Centers and Networking, and is based in Vancouver, Canada (with flexibility to collaborate across global time zones).

What you'll do

  • Scout, evaluate, and compare hardware options and colocation facilities, partnering with Engineering to align decisions with performance and cost objectives.
  • Design and deploy a cloud expansion strategy that balances reliability, performance, and efficiency across providers and regions.
  • Steer capacity planning and our expansion/upgrade strategy, using data to anticipate growth and proactively mitigate bottlenecks.
  • Design and deploy servers at scale into data centers around the globe, ensuring consistent standards and automation from day one.
  • Develop and maintain automation for a large fleet of servers, VMs, and containers, reducing toil and improving consistency across environments.
  • Work with vendors to obtain quotes, make purchases, and schedule services, including coordinating logistics for data center installations and maintenance.
  • Set up and evolve monitoring for server, network, and data center health, including alerting, dashboards, and SLO-oriented metrics.
  • Develop and maintain proper documentation for engineering staff, including runbooks, standards, and architectural diagrams.
  • Participate in a rotating on-call schedule within the larger Infrastructure Engineering division, helping drive rapid incident response and robust post-incident reviews.
  • Lead complex systems and network troubleshooting, fault analysis, and resolution, acting as an escalation point for the broader team.
  • Provide technical mentorship to other System Administrators and engineers, sharing best practices around Linux, automation, and operational excellence.
  • Partner with Security and other stakeholders on initiatives such as system hardening, compliance, and intrusion detection/prevention.
  • Occasionally travel for on-site work when remote hands are not available; an active passport is required.

Skills you'll bring

  • Background in Systems and/or Software Engineering, with a strong focus on infrastructure and operations.
  • Extensive experience with Linux, both on-premise and in the cloud, including performance tuning, troubleshooting, and automation at scale.
  • Familiarity with networking technologies: TCP/IP, DHCP, DNS, routing, firewalls, and load balancing concepts.
  • Data center setup/deployment experience, including racking/stacking, cabling standards, and remote management.
  • Exposure to cloud platforms such as GCP or AWS, and experience working in hybrid environments.
  • Demonstrated ability to keep abreast of industry standards and trends, and to translate them into practical improvements in a production environment.
  • Proven experience in a senior or lead capacity (typically 5+ years in systems administration or similar roles), including driving cross-team initiatives and mentoring others.
  • Strong communication skills and the ability to collaborate effectively with distributed teams.

For exceptional talent based in Ontario, Canada the target base salary range for this position is posted below. Our salary ranges are determined by role, level, and location. The range displayed on each job posting reflects the target range for new hire salaries for the position. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Your recruiter can share more about the specific salary range for your preferred location during the hiring process. Please note that the compensation details listed in Ontario role postings reflect the base salary only, and do not include bonus, equity, or benefits.

Ontario Salary Range
$106,500—$135,000 CAD

Why Join Dialpad

  • Work at the center of the AI transformation in business communications
  • Build and ship agentic AI products that are redefining how companies operate
  • Join a team where AI amplifies every employee's impact
  • Competitive salary, comprehensive benefits, and real opportunities for growth

We believe in investing in our people. Dialpad offers competitive benefits and perks, cutting-edge AI tools, and a robust training program that help you reach your full potential. We have designed our offices to be inclusive, offering a vibrant environment to cultivate collaboration and connection. Our exceptional culture, repeatedly recognized as a Great Place to Work, ensures that every employee feels valued and empowered to contribute to our collective success.

Don't meet every single requirement? If you're excited about this role and possess the fundamental traits, drive, and strong ambition we seek, but your experience doesn't meet every qualification, we encourage you to apply.

Dialpad is an equal-opportunity employer. We are dedicated to creating a community of inclusion and an environment free from discrimination or harassment.