Company: LP & Associates
Location: Toronto, Ontario, Canada (Remote)
Job Type: Full-time
Salary: $50,000.00–$65,000.00 per year, based on experience
About Us
LP & Associates is a fast-growing IT Managed Services & Security Provider (MSP) supporting clients across North America. We deliver responsive, high-quality technical support, cybersecurity solutions, infrastructure management, and strategic IT projects for businesses of all sizes.
About the Role
We’re hiring a full-time IT Support Specialist to join our MSP team in a remote-first role based in Canada.
This is a hands-on technical position combining L1, L2, and L3 support tickets with client project work. You’ll troubleshoot everything from everyday user issues to more complex infrastructure, networking, Microsoft 365, server, cloud, and security problems.
You’ll also work on projects including Microsoft 365 migrations, server upgrades, security deployments, network rollouts, workstation deployments, and infrastructure modernization.
This role is for someone who takes pride in clearing tickets, solving difficult problems, keeping client environments tight, and owning issues through to resolution.
Responsibilities
L1–L3 IT Support & MSP Duties
- Handle and resolve Level 1, Level 2, and Level 3 support tickets based on your technical ability and experience
- Troubleshoot desktop, application, authentication, email, printing, connectivity, and end-user issues
- Diagnose more complex Microsoft 365, Windows Server, networking, virtualization, cloud, and security issues
- Troubleshoot Microsoft 365, Google Workspace, Windows, macOS, and Linux environments
- Manage Microsoft Entra ID, user accounts, permissions, MFA, conditional access, and identity-related issues
- Manage onboarding and offboarding of users, devices, applications, and access
- Support and administer backup platforms including Veeam
- Manage and troubleshoot EDR/MDR platforms including Microsoft Defender and Sophos
- Monitor and manage client environments using RMM platforms
- Perform patching, maintenance, remediation, scripting, and automation
- Support firewalls, VPNs, switches, wireless networks, VLANs, DNS, DHCP, and general network infrastructure
- Troubleshoot servers, Active Directory, Group Policy, virtualization, and related infrastructure
- Escalate issues appropriately while remaining accountable for seeing problems through to resolution
- Work directly with clients and users to communicate status, technical findings, and resolutions
- Maintain accurate ticket notes, client documentation, procedures, and configuration information
- Own your queue: prioritize effectively, resolve tickets efficiently, and avoid allowing issues to stagnate
Projects & Infrastructure Work
- Perform Microsoft 365 migrations including Exchange Online, mailboxes, SharePoint, Teams, and OneDrive
- Assist with tenant-to-tenant and Google Workspace-to-Microsoft 365 migrations
- Deploy and configure Microsoft Entra ID, Intune, and Microsoft 365 security features
- Assist with Windows Server upgrades, migrations, replacements, and infrastructure modernization
- Deploy and maintain virtualization environments including Hyper-V and VMware
- Assist with Azure deployments and cloud infrastructure projects
- Deploy security platforms, endpoint protection, MFA, conditional access, and hardening initiatives
- Configure and deploy firewalls, switches, wireless access points, VPNs, and network infrastructure
- Handle procurement, configuration, and rollout of workstations, laptops, servers, firewalls, switches, and other IT equipment
- Perform workstation and server migrations, replacements, and refresh projects
- Standardize client environments and help move infrastructure toward MSP and security best practices
- Document completed projects, configurations, credentials, diagrams, and implementation details
- Work collaboratively with other technicians on larger or more complex implementations
Qualifications
- 2+ years of experience in IT support, systems administration, MSP environments, or a similar technical role
- Comfortable handling a mixture of L1, L2, and more advanced L3-level technical issues
- Strong knowledge of Microsoft 365 and Windows desktop environments
- Working knowledge of Windows Server, Active Directory, Group Policy, DNS, DHCP, and core networking
- Experience troubleshooting firewalls, VPNs, switches, Wi-Fi, and network connectivity
- Hands-on experience with PowerShell scripting, RMM platforms, and backup solutions
- Ability to independently investigate unfamiliar technical problems and work toward a resolution
- Strong sense of ownership — you follow through and take pride in solving problems properly
- Ability to manage competing priorities between support tickets and scheduled project work
- Excellent client-facing verbal and written communication
- Strong documentation habits and attention to detail
Nice to Have
- Experience with Sophos Central
- Microsoft Defender
- Microsoft Entra ID
- Microsoft Intune
- Microsoft Azure
- Hyper-V
- VMware
- Veeam
- Google Workspace
- Firewalls and managed networking platforms
- Microsoft 365 migrations
- MSP/RMM/PSA environments
Bonus Points
- Have a home lab? Whether it’s a few Raspberry Pis, a server rack, a firewall, or a virtualized test environment, we want to hear what you’ve built, broken, fixed, and learned.
- Tinkerer mindset? We like people who experiment with new technologies, automate repetitive tasks, build scripts, test security platforms, or learn systems simply because they want to understand how they work.
Perks & Benefits
Remote-first flexibility – Work from home by default.
Private Health Services Plan (PHSP) – Tax-free reimbursement for eligible expenses including:
- Dental care, including cleanings, fillings, and orthodontics
- Prescription medications
- Medical services not covered by provincial health insurance
- Vision care, including glasses, contacts, and exams
- Chiropractic, massage therapy, physiotherapy, and more
Signed T2200 – Supports eligible remote-work expense claims.
Grow across technologies – Work across cloud, cybersecurity, networking, servers, endpoints, virtualization, and infrastructure.
L1 through L3 exposure – Develop beyond traditional helpdesk work by troubleshooting increasingly complex environments and technical problems.
Hands-on project experience – Participate in migrations, deployments, upgrades, security initiatives, and infrastructure projects rather than working exclusively from a ticket queue.
Diverse client exposure – Gain experience across industries, technologies, environments, and technical challenges.
Certification support – We’ll support your learning goals with resources, practical experience, and team mentorship.
Supportive, no-ego team – We respect your time, value your input, and believe in long-term technical growth.
Application Instructions
Apply with your resume and include a brief note about your home lab, personal technical projects, or technology interests.
Applicants who skip this will not be considered - we care about your curiosity and technical mindset as much as your credentials.
LP & Associates
LP&A supports clients across Canada and North America, with service reach and team presence in Toronto, Sudbury and Thunder Bay, Ontario; Montréal, Quebec; Winnipeg, Manitoba; Regina and Saskatoon, Saskatchewan; Edmonton and Lethbridge, Alberta; Langley, British Columbia; Moncton, New Brunswick; Halifax, Nova Scotia; and Charlottetown, Prince Edward Island.
IT Managed Services Provider (MSP), Cybersecurity/MDR, AI, Microsoft 365, Azure, AWS and Networking Services.
Visit us at www.lpassociates.ca
Job Types: Full-time, Permanent
Pay: $50,000.00-$65,000.00 per year
Benefits:
- Dental care
- Extended health care
- Mileage reimbursement
- Vision care
- Work from home
Application question(s):
- Do you have experience working at an MSP?
- What technologies does your Home Lab consist of?
Experience:
- PowerShell: 2 years (preferred)
- Windows Server: 2 years (preferred)
- Hyper-V: 2 years (preferred)
- Azure: 2 years (preferred)
- IP Networking, Switching (VLANs, etc.), Firewall, etc.: 2 years (preferred)
Language:
Location:
- Greater Toronto Area, ON (preferred)
Work Location: Hybrid remote in Greater Toronto Area, ON
