IT Help Desk jobs in Remote

LP & Associates is a Greater Toronto Area-based IT Managed Services & Security Provider (MSP) supporting small and mid-sized businesses across Canada and North America, with remote service reach and team presence across markets including Toronto, Winnipeg, Regina, Saskatoon, Edmonton, Lethbridge, Sudbury, Thunder Bay, Moncton, Halifax, and Charlottetown. We provide IT support, IT engineering, cybersecurity services, Microsoft 365 administration, cloud services, infrastructure projects, networking, backup, and ongoing technical management across a wide range of client environments. We operate as a security-forward MSP with MDR-driven services.

About the Role

We are hiring a broad, hands-on L3 MSP Engineer who is comfortable across Microsoft 365, Azure/Entra ID, Intune, MDM, Windows Server, networking (emphasis: strong on routing, switching, NAT, DHCP, DNS), automation, security tools, and infrastructure troubleshooting.

This is an L3 role, but it is still a hands-on ticket role. You will work the queue, handle escalations, resolve day-to-day issues, and take ownership of stale, unclear, recurring, or difficult tickets that need real technical ownership. Tickets are plentiful. This is not a slow internal IT role or an ivory-tower escalation-only position.

Core Responsibilities

• Provide L3 support across desktops, servers, Microsoft 365, Azure, networking, and client environments, and work regular tickets alongside escalations, not instead of them.
• Implement and support Firewalls, VPNs and Zero Trust Networking connections for secure remote access.
• Handle escalations from L1/L2 technicians and drive difficult or stalled tickets to resolution.
• Troubleshoot workstation, server, application, connectivity, DNS/DHCP/VPN/firewall, and cloud issues.
• Administer Microsoft 365 (Exchange Online, SharePoint, OneDrive, Teams, users, groups, licensing, tenant configuration) and Azure/Entra ID (identity, conditional access, networking, virtual machines).
• Support advanced networking: VLANs, routing, NAT, DHCP, DNS, VPNs, subnetting, switching, firewall rules.
• Build and maintain Power Automate workflows where appropriate.
• Keep tickets, notes, next actions, client updates, and documentation current and clear.

Required Skills

• Strong MSP experience or experience supporting multiple business environments.
• Strong Microsoft 365 and Azure/Entra ID administration experience.
• Strong networking knowledge (VLANs, NAT, routing, DHCP, DNS, VPNs, firewalls, subnetting).
• Windows Server administration experience.
• Comfort working within EDR/MDR security platforms.
• Develop scripts using Bash, Shell Scripting, Python to automate tasks.
• Experience handling technical escalations in a high-volume, ticket-driven environment.
• Ability to work independently, take ownership, and follow through with minimal supervision.
• Strong documentation and client communication skills.
• Based in Canada, able to work Eastern Time business hours, with a quiet professional home office and reliable high-speed internet.

Nice to Have

• PowerShell or broader automation experience.
• Hands-on experience with Datto RMM, Autotask, IT Glue, Sophos, Veeam, Fortinet, SonicWall, Ubiquiti, or Meraki.
• Microsoft certifications.
• A serious IT home lab, tinkerers welcome.

Perks & Benefits

• Remote-first flexibility, work from home by default.
• Private Health Services Plan (PHSP): tax-free reimbursement for dental, prescriptions, vision, chiropractic, massage, physiotherapy, and more.
• Signed T2200 to support eligible remote work expense claims.
• Exposure to cloud, security, networking, and virtualization technologies across diverse client environments.
• Certification support and mentorship.
• Bonus potential based on performance and contribution.
• Supportive, no-ego team culture focused on growth.

Who This Role Is For

Someone already operating at a strong L2/L3 or L3 level who enjoys real troubleshooting, technical variety, and a busy MSP pace, and who's curious about the security side of the business, not just the plumbing.

Who This Role Is Not For

• Not a junior helpdesk role.
• Not a slow-paced internal IT role.
• Not for someone who only wants escalations and doesn't want to work tickets.
• Not for someone who needs one environment, a quiet queue, or constant direction.

Bonus Points - Home Lab

• Have an IT Home Lab? Whether it’s a few Raspberry Pis, a server rack, or a virtualized test environment - we want to hear about it
• Tinkerer mindset - enjoys experimenting, learning new tools, or automating tasks

How to Apply

Please submit:

• Your resume and LinkedIn profile.
• A short summary of your Microsoft 365, Azure, networking, and MSP experience.
• Details on your IT home lab or personal technical projects, what you virtualize on, what networking/firewall gear you run, what VLANs you have set up, and what you learned building it.

Applicants who skip the home lab / technical interests section may not be considered.

Visit us at www.lpassociates.ca

Pay: $65,000.00-$75,000.00 per year

Benefits:

• Casual dress
• Company events
• Dental care
• Extended health care
• Mileage reimbursement
• Paid time off
• Tuition reimbursement
• Vision care
• Work from home

Application question(s):

• Are you located in Canada?
• Do you have experience working in an MSP?

Experience:

• Firewalls, VPNs, NAT: 3 years (preferred)
• Advanced Networking: VLANs, Routing, Switching: 3 years (preferred)
• Power Automate: 1 year (preferred)
• Microsoft 365 Administration: 3 years (preferred)
• Windows Server: 3 years (preferred)
• Windows Desktop Troubleshooting: 3 years (preferred)
• Azure / Entra ID: 2 years (preferred)

Language:

• English (required)

Work Location: Remote