Senior IT Specialist
Location: GTA, Ontario, Canada (Remote-First | Occasional On-Site at Client Locations)
Employment Type: Full-Time, Permanent
Industry: Managed Services / Information Technology
About Us
Toolbox 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 Opportunity
We 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 Do
Technical 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 Bring
Required 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 Online, Intune / Endpoint Manager
- Proficiency with web infrastructure, domains, DNS and Name Servers (Cloudflare, AWS)
- Strong networking fundamentals: TCP/IP, VLANs, firewalls, VPN, SD-WAN, and experience with vendors such as Fortinet, Cisco Meraki, Ubiquiti, or similar
- Strong proficiency with Windows Server (2016/2019/2022/2025) environments (Active Directory, DNS, DHCP, Group Policy) and virtualization (Hyper-V)
- Strong experience with Windows and macOS client computers, HPE and Dell and Lenovo business servers, Apple and Android mobile and tablet devices
- Strong cybersecurity experience with tools, frameworks, and best practices (MFA, EDR, SIEM, vulnerability management)
- Proficiency with RMM and PSA platforms (ConnectWise, Datto, NinjaRMM, Kaseya, or similar), and backup and disaster recovery solutions (cloud and local based BCDR)
- Demonstrated experience leading technical projects and guiding junior to intermediate technicians
- Excellent written and verbal communication skills; ability to present technical information to a non-technical audience
- Strong organizational and time management skills with the ability to manage multiple concurrent projects and priorities
- Excellent attention to detail, delivers work that rarely needs correcting
- Valid Ontario driver's licence, access to a reliable vehicle
Nice to Have
- Scripting and automation experience (PowerShell, Python, or similar)
- API Integration experience (internal systems, cloud platforms, APIs)
- MDM and Apple Business experience (Jamf, Addigy, or similar)
- Relevant certifications: Microsoft (MCSA, MCSE, MS-900, AZ-900, AZ-104), CompTIA (Network+, Security+), ITIL, Cybersecurity and enterprise technologies
- Familiarity with ITIL frameworks or formal change management processes
- Experience managing distributed or remote teams
- Experience supporting regulated industries (legal, finance, healthcare) and familiarity with compliance requirements relevant to businesses in Ontario and Canada (PIPEDA, PHIPA)
What We Offer
- Competitive compensation: $76,000 – $90,000 annually, commensurate with experience
- Remote-first work environment with flexible/hybrid work arrangements
- Mileage reimbursement for on-site travel
- Discretionary Bonus with spot bonuses and end of year bonus
- Overtime Pay for all hours worked beyond standard
- Paid vacation commensurate with experience, in addition to paid personal and sick days
- Professional development budget for certifications and training
- Company-provided equipment to support your remote setup
- A collaborative, supportive team that values your expertise, input, and a culture of knowledge-sharing and continuous improvement
- Meaningful, varied client work, no two days are the same
- Opportunity to make a real impact at a growing company with room for career advancement
How to Apply
If you're a technically sharp, client-focused leader ready to take on a high-impact role, we'd love to hear from you.
Please submit your resume and a brief cover letter outlining your relevant experience. Include the word TBC and a technical challenge you're proud of solving via our Indeed.ca posting.
We thank all applicants for their interest; however, only those selected for an interview will be contacted.
Job Types: Full-time, Permanent
Pay: $76,000.00-$90,000.00 per year
Benefits:
- Mileage reimbursement
- Paid time off
- Work from home
Work Location: Hybrid remote in Mississauga, ON L5N 2X7
