About Us The McDougall Insurance Group is one of Canada’s largest insurance brokerages, with more than 1,250 employees across 90 locations in Ontario, Alberta, and Nova Scotia. Our IT professionals are aligned to five divisions McDougall, McFarlan Rowlands, Duliban, Drayden, and MHK which in turn support an ever-growing network of locally recognized names. With over a century of success, we combine deep local relationships with an entrepreneurial mindset—and a clear vision to build a modern, scalable organization.

Looking ahead, our ambition is significant: we plan to more than double in size over the next five years through acquisitions and technology-enabled growth. Our IT leader will play a central role in making that vision a reality.

The Opportunity

This is a high-impact leadership role—not a traditional IT position. You will play a key role in shaping the future of technology within a growing organization, transforming a group of successful but decentralized IT teams into a unified, enterprise-grade function built for scale.

Bringing both hands-on expertise and leadership credibility, you will lead infrastructure and end-user modernization, enable seamless integration of acquisitions, and establish scalable, consistent standards across a multi-division environment. You’ll initially lead the IT team of the largest division, McDougall Insurance & Financial, while influencing across all five divisions, building alignment, trust, and a shared approach to how technology supports the business.

Responsibilities

- Direct, mentor, and empower the IT professionals across divisions, building strong partnerships with divisional leadership while driving enterprise technology priorities and fostering a collaborative culture that balances local responsiveness with organization-wide consistency
- Assess and evolve the IT operating model, establishing clear structures, roles,



and accountability while shaping a scalable team and organizational design to support ongoing growth
- Lead the consolidation of multiple Microsoft environments into a unified, cloud-based platform, modernizing identity (Entra), endpoint management (Intune), and security capabilities while ensuring the reliability, availability, and evolution of both cloud and on-premises infrastructure
- Maintain reliable, secure, and highly available branch infrastructure and support while transitioning from legacy remote-desktop models to secure, modern end-user computing
- Build and execute a scalable M&A; integration framework, leading tenant migrations, user onboarding, identity integration, and device transitions across acquired businesses
- Assess acquired environments and drive pragmatic integration strategies to accelerate synergies, standardization, and operational efficiency across the organization
- Translate business priorities along with technology risks and technical debt into a pragmatic, actionable technology roadmap to support organizational scale and growth
- Develop and manage the annual IT operating and capital budgets, technology procurement, software licensing, and vendor contracts, ensuring investments align with business priorities and deliver measurable value
- Foster and evolve relationships with MSPs, vendors, and external partners, while partnering with enterprise partners in cybersecurity, data, and application development

What You Bring

- 15+ years of progressive IT experience, including leadership in infrastructure and operations within complex,



multi-site environments
- Proven track record of leading large-scale transformations, including cloud migrations, Microsoft ecosystem modernization (Windows Server, Azure, M365, Active Directory, Entra, Group Policy, Intune, hybrid Exchange environments), and M&A; integrations
- Hands-on expertise in modern, cloud-first architectures, with strong knowledge of identity, endpoint management, and cybersecurity fundamentals
- Experience designing and supporting enterprise virtualization, storage, backup, and disaster recovery solutions (e.g., VMware vSphere/ESXi, SAN infrastructure, Veeam Backup & Replication)
- Skilled at leading through influence in decentralized or matrixed organizations, building alignment without formal authority, communicating effectively with executives, and leading organizational change across both technical and non-technical teams
- Experience in high-growth, acquisition-driven organizations, ideally within regulated, distributed industries (e.g., insurance, financial services, healthcare)
- Exposure to enterprise-level capabilities, including cybersecurity governance, enterprise architecture, and data platforms

What We Offer:

- A competitive salary and performance bonus
- A supportive and inclusive culture where diversity is valued
- A competitive employee health and dental benefits program including long term disability
- A competitive pension plan
- Paid vacation time

We are proud to be an equal opportunity employer. We aim to find individuals who are passionate about their work and treat others with dignity and respect.

If you need assistance or an accommodation, you may reach out to our Human Resources Department through our website:

https://www.mcdougallinsurance.com/contact/

Job Type: Full time

Work Location: In person in Belleville, Ontario or Markham, Ontario

📌 Director of IT (Toronto)
🏢 McDougall Insurance u0026 Financial
📍 Toronto