Technical Support Specialist jobs in Waterloo, ON

Company Overview:

WaterlooIT is a dynamic and client-focused Managed Service Provider committed to delivering exceptional IT support to our valued clients. We prioritize customer service and continuous improvement, ensuring that our team members grow alongside the business while consistently exceeding client expectations.

Position Summary

Please note: This posting is not for a defined vacancy; however, we continuously seek strong talent and are willing to build an opportunity around the right candidate.

We welcome applications from skilled Tier Two Technicians who are passionate about delivering high-quality support. At WaterlooIT, Tier Two Technicians serve as the final point of escalation, handling complex configurations, recurring issues, and advanced problem resolution. The ideal candidate demonstrates a strong commitment to customer service, takes a proactive approach to troubleshooting, and is eager to continuously develop their technical expertise while contributing to the team’s overall success. This position plays a vital role in delivering timely, professional, and high-quality IT support to our clients.

Key Responsibilities

Customer Service First: Prioritize customer service, ensuring all interactions are friendly, respectful, and solution-oriented.

Critical Thinking: Apply strong analytical and problem-solving skills to diagnose and resolve complex technical issues efficiently.

Ticket Management:

• Answer incoming phone calls promptly and professionally.
• Work on assigned tickets, ensuring timely resolution.
• Ability to go onsite to clients.
• Log at least 7 hours of productive time daily on ticketing activities.
• Review and update every assigned ticket daily.
• Follow established company procedures to adhere to quality standards.

Continuous Improvement:

• Actively seek opportunities for self-improvement and skill development.
• Contribute to the teams’ success by sharing knowledge and supporting colleagues.
• Embrace feedback and demonstrate a willingness to enhance processes and workflows.

Qualifications

Technical Skills:

• Minimum 5 years of experience troubleshooting hardware, software, and network issues, preferably within an MSP environment (2+ years at the Tier One level and 2+ years at the Tier Two or higher level).
• Proven experience configuring and maintaining network equipment (switches, routers, firewalls).
• Strong understanding of managing Microsoft environments, including Windows OS, Office 365, and Active Directory.
• Experience with Microsoft 365 administration (Exchange Online, SharePoint, Teams, and compliance/security).
• Familiarity with Cloud and virtualization environments (Azure, Hyper-V, VMware).
• Experience with remote monitoring and management (RMM) and ticketing systems.
• Understanding of cybersecurity fundamentals, including MFA, EDR, and firewall management.
• Bonus: Experience automating or scripting routine tasks (e.g., PowerShell).
• Bonus: Experience mentoring Tier One technicians.

Certifications:

• CompTIA Network+
• CompTIA Security+
• Microsoft Azure Administrator Associate (AZ-104)
• Microsoft Modern Desktop Administrator (MD-102)
• Firewall certification (stack-specific)

Soft Skills:

• Excellent communication skills, with a strong customer service orientation.
• Ability to multitask and manage time effectively.
• Attention to detail and the ability to follow detailed checklists.
• Self-motivated and able to work independently as well as in a team environment.

Why Join WaterlooIT?

• Supportive and growth-oriented work environment.
• Opportunities for professional development and training.
• Competitive salary and benefits package.

To Apply:

If you are passionate about IT support, dedicated to customer service, and eager to contribute to a growing team, we encourage you to apply. Please include a cover letter with your application to be considered for this role.

Do not Apply If:

• You are unable to commute — This is an in-office role.
• You do not have valid transportation for client onsite visits as required.
• You have less than 5 years of relevant IT support experience.
• You are not comfortable working in a fast-paced environment where critical thinking and self-motivation are essential.
• You are unable to commit to logging 7 hours of productive ticket management time daily.

Please Note: This advertisement provides a general overview and is not a comprehensive job description. The specific responsibilities will be customized based on the skills and strengths of the successful candidate. Compensation will be commensurate with relevant experience and certifications.

Job Type: Full-time

Pay: $60,000.00-$95,000.00 per year

Benefits:

• Dental care
• Paid time off
• Vision care

Ability to commute/relocate:

• Waterloo, ON N2L 5C6: reliably commute or plan to relocate before starting work (required)

Experience:

• IT support: 5 years (required)

Licence/Certification:

• CompTIA A+ (required)
• Microsoft Certified: Azure Fundamentals (preferred)
• CCNA (preferred)

Work Location: In person