This role is responsible for managing the daily operations of the IT Help Desk team, ensuring exceptional customer service, driving continuous improvement, and upholding Information Technology Infrastructure Library best practices for managing Incidents, problems, and changes. The ideal candidate will have a passion to inspire teams, maintain strong hands-on technical abilities, and set the standard for service excellence within the organization.

What you will do:

Team Leadership & Development

• Lead, mentor, and develop the Help Desk team, fostering accountability, collaboration, and continuous learning.
• Set clear performance expectations, conduct regular coaching sessions, and identify opportunities for team and individual growth.

Customer Service Excellence

• Ensure every interaction delivers a positive, solution-focused experience for end-users.
• Monitor and improve IT support processes to ensure timely and effective resolution of incidents and service requests.
• Demonstrates exceptional customer service skills when interacting with high-profile and executive-level stakeholders. Ensures prompt, discreet, and personalized support that reflects professionalism, empathy, and a deep understanding of business-critical needs.
• Set the example for empathetic, proactive, and effective communication, handling escalations professionally and with care.
• Maintains a proactive approach to issue resolution, communicates with clarity and confidence, and consistently delivers a seamless support experience that upholds the organization's standards for white glove service.

Technical Oversight

• Maintain up-to-date technical expertise to support the team in troubleshooting complex issues, guiding root cause analysis, and implementing best practices.
• Participate in technical problem-solving and keep current with emerging support technologies.
• Coordinate with other IT teams (infrastructure, security, applications) to resolve complex issues.
• Leverage AI to improve customer service and technical capabilities of the team

Stakeholder Communication

• Provide regular reports and updates to senior management on problems, support performance and initiatives.
• Foster strong relationships with internal departments and external vendors.

Incident Management (ITIL)

• Oversee all aspects of Incident Management according to ITIL standards, ensuring that incidents are logged, prioritized, assigned, and resolved within agreed service levels.
• Actively monitor incident trends, develop strategies to reduce recurrence, and communicate status updates to stakeholders.

Problem Management (ITIL)

• Lead the Problem Management process, identifying underlying issues behind repeated incidents.
• Facilitate root cause analysis, document known errors, and drive the implementation of long-term solutions to prevent future disruptions.

Change and Risk Management (ITIL)

• Administer the Change Management process to ensure that all modifications to systems and infrastructure are thoroughly assessed, approved, and communicated.
• Minimize risk by ensuring changes are implemented with minimal disruption and maintain thorough documentation for all changes made.

Process Management & Continuous Improvement

• Analyze and enhance help desk processes, develop and update knowledge bases, and implement improvements to maximize efficiency, effectiveness, and compliance with ITIL standards.
• Monitor key metrics ( KPIs) and customer feedback to identify trends and areas for enhancement complex issues.
• Analyze support trends and recommend proactive solutions to reduce recurring issues. Lead or support IT projects related to end-user services and support tools.
• Oversee asset management, including hardware/software inventory and lifecycle.
• Manage some IT-related purchasing processes, including order placement, budget adherence, and invoice reconciliation, ensuring compliance with organizational procurement policies.

Incident & Request Fulfillment

• Oversee the timely resolution of incidents and service requests, ensuring adherence to SLAs and organizational policies.
• Coordinate resources and prioritize tasks to meet evolving business needs.

Stakeholder Collaboration

• Partner with IT leadership, business units, and external vendors to align support with organizational objectives and facilitate effective communication across teams

Reporting & Metrics

• Track team performance and service quality through KPIs, prepare regular reports, and present actionable insights to stakeholders.

Change Enablement

• Learn/Possess a deep understanding of existing technologies used and enable their optimal and effective use.
• Support the implementation of new technologies, processes, automations, and systems by preparing the team for change, ensuring thorough communication, and reinforcing best practices.

What you will bring:

• Bachelor’s degree in information technology, Computer Science, or related field, or equivalent experience.
• Minimum five (5) years in IT support, with at least three (3) years in a supervisory or management role.
• This role requires a minimum of 3 days per week working in our Cambridge, ON office.
• Demonstrated experience with ITIL frameworks, like Incident, Problem, and Change Management.
• Experience with help desk systems, ITIL practices, and support metrics. Including, but not limited to, Microsoft Intune and ManageEngine
• ITIL certification is required
• CompTIA A+, Microsoft, or equivalent certifications considered assets.
• Familiarity with cybersecurity and compliance standards.
• Experience in delivering exceptional customer service in a technical support environment. Strong technical competence with a broad understanding of desktop, network, cell phone, and software troubleshooting.
• Outstanding interpersonal and communication skills, with a passion for people leadership and team development.
• Analytical mindset with the ability to identify, track, and resolve recurring issues and recommend process improvements.
• Adaptable, proactive, and focused on driving positive change within the organization.

Who we are:

Proudly independent and Canadian-owned, Cowan Insurance Group has been a true market leader in the insurance industry since 1927. With an extensive range of product offerings and integrated commercial and personal insurance, group benefits, and wealth management solutions, we provide our clients with outstanding customized, comprehensive insurance and risk management professional advice and placement.

Recognized as one of Canada's Most Admired Cultures and a Canada's Best Managed Companies Platinum Club Member, Cowan Insurance Group's award-winning client-centric approach emphasizes innovation, excellence, and collaboration. Join our team as we prepare for our centennial celebration in 2027!

What sets us apart?

Be in good company

Integrity matters. It drives our award-winning workplace culture and fuels our collective desire to help our clients, employees, and communities thrive.

Challenge your thinking

You're valued for your passion, drive and creativity. The pace is fast but the work is meaningful, interesting, and complex, just the way you like it.

Grow together

We believe in your potential. If you’re looking to develop your expertise with learning opportunities and mentoring, we’ll make that happen.

Benefits and perks

• Competitive salary
• Participate in our comprehensive benefits plan on day one — no waiting period
• Company-matched Retirement Savings Plan
• Company-paid training and development courses
• Community involvement
• Hybrid work environment

Are you interested?

Please Apply!

This position is subject to appropriate background checks that may include, credential, employment, credit, criminal and reference checks.

While we appreciate the interest of all applicants, we will contact only those selected for interviews. If you are an applicant with disabilities and require accommodations, please let us know at the time of our contact so that we may arrange for their provision.

We are an Equal Opportunity Employer. Candidates will be selected strictly on the basis of an individual's technical qualifications, knowledge and experience, as they relate to the requirements of a particular position. Selections will be made without regard to: age, ancestry, colour, race, citizenship, ethnic origin, place of origin, creed, disability, family status, marital status, gender identity, gender expression, record of offences, sex, or sexual orientation.

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