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

Toolbox Cloud

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Senior IT Specialist