Overview:
It’s an exciting time to be at OSL Retail Services, working for a people focused company that’s at the top of its game. The momentum we’ve generated in recent years with our commitments to client customers, innovation, business results, and an entrepreneurial spirit has created energy, enthusiasm, and engagement among our employees that is pushing us to new heights. And we’re on the lookout for talented people who share our vision and values and want to join us in this journey. At OSL, our culture is our foundation. Passionate employees, great customer service and long-term relationships are all built upon that foundation. We value people, passion, honesty, respect, and integrity.

REQUIRED KNOWLEDGE, SKILLS, AND ABILITIES:

• Minimum of two years of experience with Microsoft Azure and Office 365 cloud services, implementing solutions using IaaS, PaaS, and SaaS.
• Enterprise experience with Windows Server, Windows 1 /11, Active Directory, Exchange, IIS, MS SQL, VMware, Citrix, Microsoft Azure, O365, and Hybrid Cloud Identity (Microsoft Entra ID).
• Familiarity with MDM and corporate device management (Intune/Autopilot).
• Understanding of security fundamentals and governance.
• In-depth knowledge of networking technologies and protocols.
• Experience with monitoring solutions (both network and software).
• Strong systems administration skills, including troubleshooting Windows desktops and servers, patch management, high availability systems, and database servers.
• Experience with IT Service Management (ITSM).
• Automation-first mindset to ensure scalability as the organization grows.
• Relevant certifications (e.g., Microsoft 365 Certified, CompTIA Server+/Security+/Network+, CCNA, etc.) are a plus.

QUALIFICATIONS:

• 5+ years of demonstrated experience in the field.
• Strong knowledge of networking protocols and services (TCP/IP, DNS, DHCP, VPN, etc.).
• Experience with Fortinet hardware and ecosystem
• Experience with cloud platforms like AWS, Azure, or GCP is a plus.
• Expert or near-expert skills with Windows, Linux, networking, storage, and containerization
• Experience with server provisioning and configuration management, utilizing tools such as Terraform, Ansible or Chef, delivering Infrastructure as Code
• Experience with database administration of MSSQL and PostgreSQL
• Observability, monitoring and alerting with tools like Prometheus and Datadog

WHAT WE OFFER:

• A competitive base salary of $85-115K plus bonus
• Vacation plus additional flex days
• Comprehensive benefits
• RRSP matching program
• Training and development opportunities to grow your career with one of Canada’s Best Managed Companies
• A supportive workplace culture and work environment
  If this sounds like you and you’re excited to be a member of our team, please apply now.
  We thank all interested applicants; however, only qualified candidates will be contacted. This position requires the successful completion of a criminal background check.
  Disclaimer: 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.
  OSL is committed to an inclusive workplace that does not discriminate against race, nationality, religion, age, marital status, physical or mental disability, sexual orientation, gender, or gender identity. We believe in diversity and encourage any qualified individual to apply.

ABOUT THE ROLE: 5 DAYS IN MISSISSAUGA OFFICE

The Senior Windows Administrator manages and supports business productivity suites and communication systems. You will set up collaborative environments within Microsoft 365. Advise on utilization of Microsoft 365 services, like Teams, Intune, Power Platform solutions, etc. You have experience with EMS (Azure AD, Intune, Information Protection, etc.) This role involves working on complex projects, including evolving existing systems and implementing new technologies.

KEY RESPONSIBILITIES:

• Provision and configure systems using technologies such as Microsoft Teams, Microsoft Intune and Autopilot, Microsoft 365, Azure Entra ID
• Administration of Windows servers and desktops
• Implement and enforce cybersecurity measures to protect systems and data.
• Monitor network performance and troubleshooting issues to ensure seamless connectivity and maximum availability.
• Collaborate with cross-functional teams to implement and support IT solutions.
• Conduct regular system audits to ensure compliance with security policies.
• Stay updated on emerging security concerns and establish processes for critical patch management, advisory circulation, and security practice training.
• Create, maintain, and update documentation for projects and existing systems.
• Configure and manage VPNs, firewall policies, and VLANs; perform traffic monitoring and packet capture analysis.
• Develop and maintain installation and configuration procedures and network-related documentation.
• Research and recommend innovative, preferably automated, approaches for system administration tasks.
• Ensure high availability, scalability, redundancy, and corporate infrastructure security.