MSP Technical Engineer

About the Role

We're looking for a hands-on, technically sharp professional who can support our clients day-to-day and confidently carry out client projects that move their businesses forward. This role blends technical troubleshooting, project execution, consultative discovery work and technical documentation. You'll meet with client leadership, understand business challenges, translate them into IT solutions, and then deliver those solutions with precision.

Key Responsibilities:

Client Support (Tier 2–3)

• Provide remote and on-site troubleshooting across Windows, macOS, Microsoft 365, Azure, networking, VoIP, and business applications.
• Own escalated service tickets and deliver timely, accurate resolutions.
• Communicate clearly with clients: set expectations, provide updates, and close loops.
• Document work thoroughly within Halo (PSA).
• Manage identity and access across Microsoft 365 and Azure AD (Entra ID): licensing, MFA, Conditional Access, app assignments, device enrollment.
• Support core infrastructure including servers, VMs, firewalls, switches, wireless networks, and cloud services.

Technical Discovery & Client Engagement

• Conduct discovery sessions with users, managers, directors, and executives to understand workflows, challenges, and business objectives.
• Identify technology gaps and recurring issues, offering proactive recommendations.
• Participate in QBRs, roadmap planning, and vCIO discussions.
• Translate business challenges into actionable technical solutions and assist in drafting scopes of work.
• Build strong, trusted relationships with client stakeholders.

Project Implementation

• Execute small to mid-sized projects independently or with team support, including:
• Microsoft 365 and Azure migrations
• Teams Voice & Ring Central deployments
• SharePoint site builds, migrations from on-premise file stores
• Firewall/switch/Wi-Fi upgrades (primarily Ubiquiti Unifi network components)
• Security stack rollouts and assisting with Switchboard Stack lifecycle and guidance
• MDM deployments (Intune/Autopilot or Jamf)
• Follow project plans, escalate blockers early, and keep stakeholders aligned.
• Participate in kickoff calls and internal handoff meetings.
• Maintain project documentation, diagrams, status notes, and post-implementation reports.

Technical Expertise:

Microsoft 365 & Azure

• Administer Microsoft 365: Exchange Online, Teams, SharePoint, OneDrive.
• Manage Azure/Entra resources: Conditional Access, App Registrations, AVD (optional), resource management, and policy alignment.
• Support cloud identity, SSO, guest access, and hybrid identity configurations.

PowerShell & Automation

• Use PowerShell to automate user/device management, reporting, and configuration tasks.
• Work with common modules: Microsoft.Graph, ExchangeOnlineManagement, AzureAD (legacy), MSOnline.
• Build repeatable scripts and deployment routines.
• Experience with automation systems such as Power Automate, Retool and N8N, and experience with API calls via REST, GraphQ

Networks & Systems

• Troubleshoot VLANs, VPNs, routing, DHCP/DNS, and Wi-Fi.
• Understand firewalls, switching, and network topology best practices.
• Support Hyper-V and Windows Server environments, including hybrid AD setups.
• Work comfortably with security tools: EDR, ITDR, email filtering, backup/DR.

Service Delivery Excellence

• Follow MSP processes for ticketing, documentation, escalation, and change management.
• Suggest improvements to both client environments and internal best practices.
• Maintain strong client satisfaction through proactive communication and ownership.
• Participate in after-hours/on-call rotation as required.

Skills & Qualifications

Required:

• 3–5 years in technical support, systems administration, or MSP operations.
• Strong Microsoft 365 and Azure/Entra administration experience.
• Practical PowerShell skills (comfortable modifying and troubleshooting scripts).
• Solid troubleshooting across Windows 10/11, networking, cloud identity, and SaaS platforms.
• Ability to meet with client management teams, understand business needs, and communicate clearly.
• Experience delivering IT projects end-to-end.
• Valid driver's license and ability to travel to client sites.

Nice to Have

• Experience with Datto RMM, Halo PSA, Acronis, Huntress, Unifi networking.
• Teams Phone/VoIP deployment experience.
• SharePoint site design and permissioning.
• Azure or Microsoft 365 certifications.
• Experience building automation or repeatable deployment scripts in PowerShell.

Who Thrives in This Role

• Someone who can confidently talk to both end users and executives.
• Someone who enjoys variety — projects, on-site visits, cloud work, and troubleshooting.
• Someone who takes ownership and delivers clean, complete outcomes.
• Someone looking to grow into senior engineering, solution architecture, or vCIO roles.

Compensation & Benefits

• Salary Range: $70,000 – $80,000 annually (based on experience and capability).
• Health & Dental Benefits after 3 months of employment.
• 3 weeks vacation / 5 days paid sick leave.
• Professional development and certification support.
• Mileage and travel reimbursement for on-site client work.
• Flexible hybrid work environment.
• Exposure to modern cloud, security, and networking platforms.
• Clear growth paths within the organization.

Job Types: Full-time, Permanent, Fixed term contract
Contract length: 12 months

Pay: $70,000.00-$80,000.00 per year

Benefits:

• Casual dress
• Commuter benefits
• Dental care
• Disability insurance
• Discounted or free food
• Extended health care
• Flexible schedule
• Life insurance
• Paid time off
• Vision care
• Work from home

Ability to commute/relocate:

• Burlington, ON L7N 3W8: reliably commute or plan to relocate before starting work (required)

Application question(s):

• Do you have experience doing cloud migrations from onsite servers to Microsoft 365/Azure/Entra?
• If a client needs a server replaced, are you able to build a project plan, spec a replacement, quote a replacement, and implement a physical Windows server migration without extensive support through the process?
• Do you have experience migrating clients from Google Workspace to Microsoft 365?
• Do you have experience installing physical network appliances and/or network cabinets/racks and related patch cable management etc?
• Are you able to work independently and track your time appropriately and accurately? Do you have experience with client facing time tracking?
• Are you comfortable with the responsibility of having client server/system build or migration projects assigned to you to manage and work independently upon while maintaining timeframes and managing your own work schedule to complete initiatives when called for? This role comes with management and oversight but in many ways is a very independent role that requires a motivated, organized and meticulous self starter who is able to document processes, time, project scope requirements and implementation steps and scheduling without immediate ongoing top down management.

Experience:

• General MSP: 2 years (preferred)
• Automation: 1 year (required)
• General AI/Chat GPT: 1 year (required)
• In depth Microsoft 365/Entra Administration: 2 years (required)
• IT Technical Support: 5 years (required)
• Kaseya/Datto Autotask/IT Glue: 2 years (preferred)

Work Location: Hybrid remote in Burlington, ON L7N 3W8