IT Support Specialist – Level 1 / Help Desk Technician (MSP, Remote – Canada)

Company: LP & Associates

Location: Remote (Canada)

We support clients across Canada, including Manitoba, Recent Brunswick, Nova Scotia, Prince Edward Island, Alberta, and Saskatchewan.

Job Type: Full-time, Permanent

Salary: $40,000.00 – $50,000.00 per year (entry-level, based on experience)

About LP & Associates

LP & Associates is a growing IT Managed Services & Security Provider (MSP) supporting small and mid-sized businesses across North America. We deliver responsive IT support, cybersecurity services, and infrastructure projects across Microsoft 365, cloud, and on-prem environments.

About the Role

We are hiring a Level 1 IT Support Specialist / Help Desk Technician to join our remote MSP team.

This is an entry-level role, ideal for:

- Recent graduates
- Candidates currently completing post-secondary IT studies
- Self-taught technologists
- Anyone early in their IT career looking to gain hands-on MSP experience

You will focus on first-line technical support, ticket triage, and routine IT tasks, with mentorship and clear escalation paths to senior technicians. You are not expected to know everything on day one - you are expected to be reliable, curious, and willing to learn.

Key Responsibilities

Level 1 IT Support / Help Desk

- Provide first-line technical support to end users (remote)
- Triage incoming help desk tickets and follow documented procedures
- Troubleshoot common issues involving:
- Windows Windows 11
- Microsoft 365 (Outlook, Teams, OneDrive)
- Assist with user onboarding and offboarding (accounts, permissions, MFA)
- Perform routine tasks using RMM tools (monitoring, alerts, basic remediation)
- Maintain clear, accurate ticket notes and documentation
- Escalate issues appropriately when outside Level 1 scope

Learning & Development

- Shadow senior technicians on more complex issues
- Assist with project work as needed




- Build skills across MSP tools, security practices, and client environments

Tools You’ll Be Exposed To

- Datto RMM
- Microsoft 365 / Entra ID (Azure AD)
- Remote support tools
- Documentation platforms (IT Glue or similar)
- Endpoint security tools (EDR/MDR exposure over time)

Qualifications

- High school diploma (or equivalent)
- Post-secondary education in IT (completed or in progress), or equivalent hands-on experience (self-taught candidates welcome)
- Basic understanding of:
- Windows operating systems
- Microsoft 365 fundamentals
- User accounts and permissions
- Strong written and verbal communication skills
- Reliable internet connection and home workspace
- High level of professionalism, integrity, and attention to detail

Nice to Have

- Any help desk or MSP experience
- CompTIA A+ or similar entry-level certification
- Interest in PowerShell or automation
- Personal computing projects or a home lab

Bonus Points

- Have a 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

Perks & Benefits

- Remote-first flexibility - work from home by default
- Private Health Services Plan (PHSP) – tax-free reimbursement for:
- Dental care
- Prescription medications
- Medical services not covered by provincial plans
- Vision care
- Chiropractic, massage, physiotherapy, and more
- Signed T2200 to support eligible remote work expense claims
- Exposure to cloud, security, networking,



and virtualization technologies
- Diverse client environments across multiple industries
- Certification support and mentorship
- Bonus potential based on performance and contribution
- Supportive, no-ego team culture focused on growth

Application Instructions Apply with your resume and include a brief note about your home lab, personal projects, or technical interests.

Applicants who skip this will not be considered - curiosity matters here.

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: $40,000.00-$50,000.00 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):
- Do you have a home lab or personal technical projects?

This can include virtual machines, cloud labs, networking gear, scripting or automation projects, self-hosting, or anything you’ve built or experimented with to learn IT. Please briefly describe what you’ve set up, what tools or technologies you used, and what you learned from the experience.

Experience

- Windows 11 Professional: 1 year (preferred)
- PowerShell: 1 year (preferred)
- Windows Server: 1 year (preferred)
- Hyper-V: 1 year (preferred)
- Azure: 1 year (preferred)
- IP Networking, Switching (VLANs, etc.), Firewall, etc.: 1 year (preferred)

Work Location: Remote

📌 Help Desk Technician (Level 1 IT Support – MSP, Remote Canada) (Toronto)
🏢 LP u0026 Associates
📍 Toronto