RequirementsMust have:Over 7 years of progressive IT experience, including a minimum of 2 years in a senior or leadership role in a managed services or dynamic multi-client environmentExtensive, hands‑on knowledge of Microsoft technologies, including Microsoft 365, Azure AD / Entra ID, SQL Server, Exchange Online, and Intune / Endpoint ManagerProficiency in web infrastructure, including domains, DNS, and Name Servers such as Cloudflare and AWSStrong understanding of networking concepts such as TCP/IP, VLANs, firewalls, VPN, and SD‑WAN, with experience using vendors like Fortinet, Cisco Meraki, or UbiquitiSolid expertise in Windows Server environments (2016/2019/2022/2025), including Active Directory, DNS, DHCP, and Group Policy, as well as virtualization technologies like Hyper‑VExperience with Windows and macOS client systems, along with HPE, Dell, and Lenovo business servers, and familiarity with Apple and Android mobile devicesStrong background in cybersecurity tools and best practices, including MFA, EDR, SIEM, and vulnerability managementCompetence with RMM and PSA platforms (ConnectWise, Datto, NinjaRMM, Kaseya, etc.) and backup/disaster recovery strategiesProven track record of leading technical initiatives and mentoring junior to intermediate techniciansExceptional communication skills, both written and verbal, with the capacity to clearly convey technical information to diverse audiencesStrong organizational and time management skills to juggle multiple concurrent projectsKeen attention to detail,



consistently delivering high‑quality work with minimal corrections requiredValid Ontario driver’s license with access to a dependable vehicleResponsibilities:Serve as the primary technical escalation point for intricate infrastructure, networking, and systems challenges across the client base – Lead the design and execution of solutions encompassing cloud platforms (Microsoft Azure, Microsoft 365), security measures, on‑premises infrastructure, networking, and endpoint management – Direct the technical trajectory of client and special projects from initial scoping to final handover, ensuring adherence to quality, consistency, and documentation standards – Collaborate with vendors and third‑party partners on escalations, procurement, and project execution – Perform architecture reviews and provide recommendations aligned with client goals and industry best practices – Offer daily technical guidance and mentorship to a team of systems administrators and support technicians – Engage in the recruitment, onboarding, and continuous professional development of technical personnel – Cultivate a cooperative, knowledge‑sharing team culture through documentation, internal training, and regular technical discussions – Act as a trusted technical advisor to key client stakeholders,



translating business needs into actionable technology solutions – Attend virtual client meetings and in‑person visits as necessary to facilitate project delivery, installations, assessments, and relationship management – Clearly articulate complex technical concepts to both technical and non‑technical audiences – Create, document, and enforce technical standards, workflows, and standard operating procedures across the team – Maintain comprehensive documentation of environments, procedures, and project work in relevant platforms – Identify opportunities to enhance operational efficiency through automation and process improvements – Work with account management and sales teams in scoping, technical evaluations, and solution proposalsCompany:At Toolbox Cloud, we are a rapidly growing IT services firm with 15 years of solid experience in delivering enterprise‑level IT solutions across various sectors. Our dedicated team designs, implements, and manages diverse technology environments to help clients focus on their core business. We are looking for a Senior IT Team Leader to enhance our managed IT services for our client portfolio. This predominantly remote role will involve occasional visits to client locations in Ontario, depending on project needs. We offer competitive compensation ranging from $86,000 to $110,000 annually, a remote‑first work culture with flexible arrangements, mileage reimbursement for travel, a discretionary bonus structure, overtime pay, and a professional development budget. You will join a collaborative team that values your expertise and insights while tackling meaningful and varied client projects.#J-18808-Ljbffr

📌 Senior It Team Lead - C$86,000 - C$110,000 A Year - Remote (Toronto)
🏢 Toolbox Cloud
📍 Toronto