60 Datadog Systems Administrator Jobs Hiring Near You

At OSL Retail Services, we believe people are the heart of everything we do, and it is an exciting time to be part of something special! Our momentum is growing, and is fueled by innovation, collaboration, and a shared entrepreneurial spirit that drives real results. Founded in 2012 in Mississauga, Ontario, OSL delivers customized sales solutions in retail, direct sales, and customer acquisition, all built on a foundation of integrity, respect, and passion. Our culture thrives on connection, purpose, and growth. If you're looking for a place where your talents are valued, your ideas matter, and your career can grow, we'd love to meet you.

The Opportunity:

We are recruiting a System Administrator. Reporting to the VP IT, in this role, you will be instrumental in managing our corporate infrastructure, cybersecurity and cloud services. Your expertise will ensure the highest reliability and performance, supporting our commitment to delivering exceptional service to our clients and customers. This role involves working on complex projects, including evolving existing systems and implementing new technologies. It will be based out of our corporate office in Mississauga, Ontario.

What You'll Do:

• Oversee corporate network operations: Administer network infrastructure, firewalls, VPNs, and maintain robust network troubleshooting and security measures.
• Develop and maintain documentation: Prepare and update system configurations, mappings, process documentation, and problem management records.
• Supervise desktop and cloud infrastructure: Manage both on-premises and Azure cloud environments.
• Continually monitor OSL's IT landscape: Maintain vigilant oversight of capacity and performance metrics.
• Support IT strategy and service improvement: Actively participate in tactical planning and contribute to the enhancement of all IT service deliveries.
• Administer application servers: Oversee a diverse environment comprising Windows, Linux, and Azure-based resources.
• Enforce security controls: Ensure the implementation of best-practice security measures across all systems.

Required Knowledge, Skills, and Abilities:

• Strong engineering foundation with hands-on experience in network architecture, network security, and enterprise network operations, including firewalls, switches, access points, VPNs, and MPLS environments.
• Proven expertise in automation, configuration management, and infrastructure reliability, with a solid understanding of security best practices.
• Experience administering and supporting both Windows and Linux environments, including advanced troubleshooting and scripting capabilities.
• Proficiency in scripting and automation using tools and languages such as PowerShell, Bash, and/or Python.
• Hands-on experience with monitoring, observability, and alerting platforms, including tools such as Zabbix, Azure Monitor, Prometheus, Grafana, and log management solutions (e.g., ELK stack, Loki, Graylog).
• Working knowledge of Microsoft Entra ID / Active Directory and identity-based access controls within hybrid or cloud-enabled environments.
• Ability to take full ownership of technical deliverables, from design through implementation and ongoing operational support.
• Strong collaboration and communication skills, with the ability to clearly explain technical concepts and risks to non-technical stakeholders.
• Experience supporting production environments, including participation in after-hours on-call rotations as required.
• Familiarity with ITIL practices, including Incident, Change, and Problem Management, and experience working within structured operational processes.

What you've done:

• 3+ years of experience supporting enterprise-scale environments across networking, Windows and Linux systems, and cloud services.
• Strong understanding of core networking concepts and protocols, including TCP/IP, DNS, DHCP, VPN technologies, and routing.
• Experience managing and operating Fortinet network hardware and security solutions; Fortinet certifications are considered an asset.
• Exposure to public cloud platforms such as Microsoft Azure (preferred), AWS, or GCP, including hybrid networking scenarios.
• Experience with infrastructure provisioning and configuration management using Infrastructure as Code tools such as Terraform, Ansible, and/or Chef.
• Working knowledge of database administration concepts, with experience supporting platforms such as Microsoft SQL Server and PostgreSQL.
• Experience implementing and maintaining observability, monitoring, and alerting solutions, including tools such as Prometheus and Datadog.

Working Conditions:

• Flexibility to work on various schedules, including evenings and weekends, as required.

What's in it for you:

• Competitive base salary: $71K-$86K plus bonus.
• Generous time off: Start with 3 weeks of vacation, plus extra flex days to recharge.
• Comprehensive benefits package: Includes medical, dental, vision, health spending account, and Teladoc virtual care.
• Retirement support: Company-sponsored savings plan to help build your financial future
• Career growth: Ongoing training, development, and programs to help you advance.
• Award-winning culture: Proud to be one of Canada's Best Managed Companies for 8 years running - now a Platinum Club member.

The Interview Process:

• Stage 1: If your profile is a match, we will invite you for a first conversation with the recruiter.
• Stage 2: The next step is a virtual conversation with the hiring manager.
• Stage 3: The final step is an in-person interview with the hiring manager and extended team members.

If this sounds like you and you're excited to be a member of our team - please apply now. 

Disclaimer: As part of our recruitment process, we utilize artificial intelligence (AI)-based tools to assist with certain stages, including initial resume screening and skills-matching assessments. These tools are designed to help our hiring team identify candidates whose experience and qualifications align closely with the requirements of the role. Please note that all final hiring decisions are made by our recruitment team.  The preceding job description has been designed to indicate the general nature and level of work performed by employees within this job. It is not designed to contain or be interpreted as a comprehensive inventory of all duties, responsibilities and qualifications required of employees assigned to this job.  In compliance with Ontario's Bill 190, we confirm that this posting represents a current existing vacancy within our organization.