Senior IT SpecialistLocation: GTA, Ontario, Canada (Remote-First | Occasional On-Site at Client Locations)
Employment Type: Full-Time, Permanent
Industry: Managed Services / Information Technology
About UsToolbox Cloud is a growing IT services company with 15 years of proven experience delivering enterprise-grade IT solutions to clients across a range of industries. Our team of dedicated professionals designs, implements, and manages technology environments, supporting everything from X-ray sensors to next-generation firewalls, Windows OS to macOS, and Google Workspace to Microsoft 365. Whether designing a de novo (ground-up) build or managing existing infrastructure, we handle the technology so our clients can focus on what they do best. We pride ourselves on a culture of continuous improvement, technical excellence, and exceptional client service, backed by single-point-of-contact support that gets our clients back to their business operations sooner.
The OpportunityWe are looking for a seasoned Senior IT Specialist to join our team and play a pivotal role in the delivery and oversight of managed IT services across our client portfolio. The ideal candidate brings deep, hands-on expertise across Microsoft cloud technologies, networking, cybersecurity, and server infrastructure. This is a hands-on leadership position for someone who thrives in a fast-paced MSP environment, is confident guiding a technical team, and takes pride in building reliable, scalable solutions.
This role is predominantly remote with periodic on-site visits to client locations in Ontario varying by project cycle — some months may have none, while active project phases may require several visits.
What You'll DoTechnical Leadership & Delivery- Serve as the senior technical escalation point for complex infrastructure, networking, and systems issues across the client portfolio
- Lead the design and implementation of solutions spanning cloud platforms (Microsoft Azure, Microsoft 365), security (including EDR/MDR), on-premises infrastructure, networking, and endpoint management
- Drive the technical direction of client and special projects from scoping through to handover, ensuring quality, consistency, and documentation standards are met
- Coordinate with vendors and third-party partners on escalations, procurement, and project delivery
- Conduct architecture reviews and provide recommendations aligned with client business objectives and industry best practices
Team Guidance & Mentorship- Provide day-to-day technical direction and mentorship to a team of systems administrators and support technicians
- Participate in hiring, onboarding, and ongoing professional development of technical staff
- Foster a collaborative, knowledge-sharing team culture through documentation, internal training, and regular technical discussions
Client Engagement- Act as a trusted technical advisor to key client stakeholders, translating business requirements into practical technology solutions
- Attend online client meetings and on-site visits as needed to support project delivery, installations, assessments, and relationship management
- Communicate complex technical concepts clearly to both technical and non-technical audiences
Standards & Process- Develop, document, and enforce technical standards, runbooks, and SOPs across the team
- Document environments, procedures, and project work thoroughly in the PSA/RMM, ITSM, and knowledge base platforms
- Identify opportunities to improve operational efficiency through automation, PSA/RMM, tooling improvements, and process refinement
- Collaborate with account management and sales to support scoping, technical assessments, and solution proposals
What You BringRequired Qualifications- 7+ years of progressive IT experience, with at least 2 years in a senior or lead technical capacity within an MSP or fast-paced multi-client IT environment
- Deep hands-on expertise with Microsoft technologies: Microsoft 365, Azure AD / Entra ID, SQL Server, Exchange