Head of Information Technology Department

Our client is in the financial services/non-profit sector is seeking a fulltime/permanent Head of IT. The organization is undergoing a major technology modernization cycle—including CRM redevelopment, portal evolution, workflow and reporting enhancement, and strengthened IT governance. This role will report directly to the CEO, and serve on the senior leadership team. They are seeking a visible, strategic, and relationship-driven IT leader to guide this transformation. Location: Toronto - Hybrid Responsibilities 1. Strategic Leadership & Executive Partnership Serve as a strategic technology advisor to the CEO and senior leadership team. Prepare executive materials, analysis, and presentations for board-level discussions. Participate in cross-organizational decision-making and strategic planning. Represent the organization's mission, values, and reputation in all internal and external interactions. 2. IT Modernization & Transformation Delivery Lead the multi-year CRM renewal and related modernization initiatives across case management, portals, workflow, and reporting. Improve project and portfolio execution maturity, ensuring clarity, prioritization, and structured delivery across concurrent workstreams. Champion innovative, forward-thinking solutions that remain practical and right-sized for a mid-sized, public-interest organization. Balance modernization with operational realities—"simple is better than complex."3. Operations, Security & Risk Management Ensure reliable IT operations across applications, infrastructure, communications systems, and support processes. Lead IT security strategy, maturity assessments, and annual security roadmaps with the managed services provider and external consultants. Integrate enterprise risk management into IT decision-making, and support business continuity planning and testing. 4. Data, Reporting & Knowledge Enablement Strengthen data governance, integrity controls, workflow automation, and reporting capabilities. Enhance internal and external reporting that supports operational insights and organizational value. Partner with knowledge management to evolve intranet usability, content accessibility, and staff enablement tools. 5. Vendor, MSP & Third-Party Oversight Manage key technology vendors—including CRM, portals, SharePoint, cloud tools, and application development partners. Maintain and strengthen a longstanding positive relationship with the managed services provider. Ensure vendor performance, alignment, and accountability across critical systems and services. 6. Team Leadership & Culture Building Lead, coach, and develop an internal IT team, ensuring clarity of roles, expectations, and performance. Build a culture of communication, reliability, and credibility with internal stakeholders. Promote continuous improvement, innovation, and practical problem-solving aligned with a mission-driven organization. Requirements: 1. Leadership & Personal Attributes Strong executive presence with the ability to communicate clearly to senior executives and governance bodies. Ethical, values-aligned leadership style consistent with public-interest, mission-driven environments. Balanced judgment—forward-thinking yet grounded in operational reality ("art of the possible"). High accountability and follow-through; known for delivering commitments. 2. Technical & Functional Expertise Significant experience leading IT teams, operations, and technology modernization initiatives. Proven success with CRM redevelopment (ideally Dynamics 365), case management systems, portals, workflow modernization, and reporting/data enhancement. Strong understanding of IT security, privacy, audit practices, and risk management. Experience overseeing MSPs and third-party vendors in cloud-based and hybrid environments. Proficiency with the Microsoft ecosystem: Dynamics 365, SharePoint, Power Platform, Microsoft 365, and cloud services. 3. Management & Execution Competencies Demonstrated ability to manage complex workloads, multiple parallel projects, and organizational priorities. Strong project, budget, and vendor management capabilities. Skilled at right-sizing solutions for mid-sized organizations; avoids unnecessary complexity. 4. Sector & Contextual Fit Background in public-interest, regulatory, non-profit, consumer-protection, member-service, or case-driven environments is ideal. Experience in claims, adjudication, customer service technology, or financial services adjacent organizations is advantageous. Ability to quickly understand the organization's mandate, operating environment, and stakeholder landscape. 5. Education & Training Post-secondary degree in Information Technology, Technology Management, or a related field. Additional certifications or training in cloud platforms, cybersecurity, project management, or Microsoft technologies are an asset.