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Job Title: Senior Technical Lead – IT & Cybersecurity (MSP)
Job ID: 79206
Location: Calgary, Alberta – Remote or Hybrid Available

Overview:
Are you a seasoned MSP professional ready to take the next step in your career? We’re looking for a Senior Technical Lead who brings deep MSP experience and a forward-thinking approach to cybersecurity, automation, and AI. This is more than a Tier 3 role—it’s a chance to lead by example, mentor others, and help guide a high-performing MSP as it evolves into a full-scale cybersecurity solutions provider. If you thrive on solving complex challenges, optimizing systems, and helping clients stay secure and efficient in today’s digital world, we want to hear from you.

What you will be doing:

• Tier 3 Leadership: Act as the escalation point for complex technical issues across systems, infrastructure, cloud, networking, and VoIP.
• Mentorship & Growth: Informally guide and support Tier 1 and 2 technicians, helping shape the team’s evolution into a formal structure.
• Cybersecurity Focus: Conduct vulnerability and risk assessments, contribute to internal audits, and support threat detection initiatives.
• Project Execution: Lead key customer projects such as cloud migrations, onboarding, and security stack rollouts.
• Automation & AI Integration: Leverage scripting (PowerShell, Python) and tools like Microsoft 365 Copilot, ChatGPT, Zapier, Rewst, and N8N to streamline workflows.
• VoIP & Network Management: Deploy and support secure voice solutions using 3CX, and maintain client infrastructure using Ubiquiti and Meraki gear.
• Client Strategy: Participate in QBRs/QSRs and help shape client IT roadmaps using tools like Kaseya MyITProcess.
• Documentation & Reporting: Maintain accurate and actionable documentation in IT Glue and other platforms.
• Team Collaboration: Work closely with the Service Desk, SOC, and third-party vendors to ensure seamless service delivery.
• Community Involvement: Join peer group calls and occasionally travel to cybersecurity conferences in North America.

What you must have:

• 5+ years of deep MSP experience, with ideally some (but not limited to) exposure to MSSP environments or security professional services.
• Strong technical expertise across Microsoft 365, Azure, Windows Server, virtualization, and networking.
• Hands-on cybersecurity experience including risk assessments, endpoint protection, vulnerability management, and basic pen testing.
• Familiarity with scripting (PowerShell, Python), automation workflows, and AI tools like Microsoft Copilot or ChatGPT.
• Experience with industry-leading MSP tools such as: Autotask, Datto RMM, N-Able, RocketCyber, Datto EDR/AV, COVE Backup, IT Glue, 3CX VoIP, Microsoft Defender for 365, MS Lighthouse, Ubiquiti, Meraki, SAAS Alerts, Telivy, CyberGuard 360, ClickUp.
• Excellent communication and documentation skills, with a proactive, solution-oriented mindset.

Nice to have:

• Microsoft 365 or Azure certifications.
• CompTIA Security+, CCNA/CCNP, or other security/networking credentials.
• Microsoft Copilot AI Essentials or other AI-centric certifications.
• Experience with security training tools, phishing simulations, or compliance frameworks.

Other Information:
Why This Role Rocks

• Career Growth: Be part of a company transforming from MSP to cybersecurity-first.
• Tech-Focused Culture: Work with cutting-edge tools in cloud, cybersecurity, and AI.
• Remote Flexibility: Work from anywhere in Canada, with optional hybrid setup for Calgary-based team members.
• Professional Development: Ongoing certifications, access to peer groups, and conference travel opportunities.
• Supportive Environment: Collaborative culture that values innovation, respect, and fun.

We’re looking for someone who’s technically strong, execution-focused, and excited to grow with a company that’s pushing into the future of cybersecurity.