Director of Information Technology (Toronto)

Position Overview

Reporting to the President & CEO, the Director, Information Technology will lead the modernization, optimization, and governance of YORK1’s technology environment. This strategic and hands‑on leadership role is responsible for enterprise infrastructure, cybersecurity, ERP systems, cloud platforms, business applications, integrations, disaster recovery, operational technologies, and digital transformation initiatives.

The Director will ensure technology platforms are secure, scalable, resilient, and aligned with YORK1’s operational and business objectives. The role will also lead the organization’s AI and intelligent automation strategy by identifying and implementing solutions that improve operational efficiency, reporting, customer experience, workforce productivity, predictive analytics, and business decision‑making.

Core Accountabilities

IT Strategy & Digital Transformation

• Execute YORK1’s IT strategy in alignment with business and operational goals.
• Lead digital transformation initiatives focused on automation, scalability, reporting, and operational efficiency.
• Partner with business leaders to identify technology solutions that enhance operations, compliance, customer service, and data visibility.
• Evaluate emerging technologies, AI solutions, and operational technologies to support growth and continuous improvement.
• Develop technology roadmaps for infrastructure, applications, cybersecurity, and enterprise systems.
• Identify and implement AI, machine learning, predictive analytics, and workflow automation opportunities.
• Establish governance, security, compliance, and acceptable‑use standards for AI technologies.

Infrastructure, Cloud & Enterprise Systems

• Oversee enterprise infrastructure including networks, servers, cloud environments, telecommunications, and end‑user computing.
• Lead infrastructure modernization initiatives, cloud migrations, upgrades, and platform enhancements.
• Manage ERP, CRM, fleet technologies, reporting platforms, and operational systems.
• Lead ERP implementation, migration, enhancement, and integration initiatives.
• Ensure enterprise systems are integrated, reliable, secure, and support business objectives.
• Establish technology standards, lifecycle management practices, and governance controls.
• Manage cybersecurity, privacy, and operational risks related to AI and third‑party technologies.

Cybersecurity, Disaster Recovery & Risk Management

• Lead cybersecurity strategy, governance, and security operations.
• Develop and maintain security policies, controls, standards, and incident response processes.
• Oversee vulnerability management, access controls, endpoint protection, and risk mitigation activities.
• Ensure business continuity through disaster recovery planning, backup management, resilience testing, and recovery readiness.
• Coordinate security assessments, penetration testing, and remediation initiatives.
• Ensure compliance with cybersecurity, privacy, and regulatory requirements.

ERP, Systems Integration & Technology Projects

• Lead enterprise ERP initiatives from planning through stabilization.
• Oversee integrations across finance, HR, CRM, fleet, operational, and third‑party systems.
• Manage cross‑functional technology projects, budgets, timelines, and business outcomes.
• Improve data governance, reporting capabilities, process standardization, and system utilization.
• Support business intelligence, analytics, automation, and predictive reporting initiatives.

IT Operations & End‑User Support

• Oversee daily IT operations, service delivery, and user support across all locations.
• Establish service standards, escalation procedures, and performance metrics.
• Ensure timely resolution of technology issues and minimize operational disruption.
• Continuously improve system reliability, uptime, service quality, and user experience.

Vendor & Technology Partner Management

• Manage relationships with vendors, managed service providers, consultants, and cybersecurity partners.
• Negotiate contracts, software licensing agreements, and service‑level commitments.
• Evaluate vendor performance, value, and alignment with business objectives.
• Oversee procurement and lifecycle management of technology assets.

Budgeting & Resource Management

• Develop and manage IT operating and capital budgets.
• Monitor expenditures and identify cost optimization opportunities.
• Prioritize investments based on business value, risk, cybersecurity exposure, and operational impact.
• Support long‑term technology planning and scalability initiatives.

Leadership & Team Development

• Lead, mentor, and develop IT team members.
• Foster a culture of accountability, innovation, collaboration, and continuous improvement.
• Build strong partnerships with operational and business leaders.
• Act as a trusted advisor on technology strategy, risk management, and operational enablement.

Key Performance Indicators

• Infrastructure uptime and reliability
• Cybersecurity maturity and incident response effectiveness
• ERP and systems integration success
• Disaster recovery readiness and testing outcomes
• End‑user support performance
• Enterprise systems adoption and optimization
• Budget management and cost efficiency
• Infrastructure modernization and cloud migration progress
• Compliance with cybersecurity and privacy requirements
• Vendor performance and service delivery
• AI and automation adoption
• Measurable efficiency gains and process improvements
• Data quality, reporting effectiveness, and analytics capabilities

Qualifications & Experience

Experience

• 7–10+ years of progressive IT leadership experience.
• Experience in enterprise systems, infrastructure, cybersecurity, or technology operations leadership.
• Experience within industrial, environmental services, transportation, logistics, construction, manufacturing, or similar operational environments preferred.
• Proven success leading ERP implementations, integrations, digital transformation, and cloud initiatives.
• Experience managing cybersecurity programs, disaster recovery, vendors, and managed service providers.
• Experience with AI‑enabled technologies, automation platforms, analytics solutions, or business intelligence tools is an asset.
• Demonstrated ability to lead complex cross‑functional technology projects.

Technical Capability

• Strong knowledge of enterprise infrastructure, networking, cloud technologies, cybersecurity, and systems architecture.
• Experience with ERP, CRM, integrations, reporting platforms, and operational technologies.
• Robust understanding of disaster recovery, business continuity, governance, risk management, privacy, and compliance.
• Knowledge of Microsoft environments, virtualization, backup technologies, and enterprise applications.
• Familiarity with AI technologies, automation tools, analytics platforms, and related governance considerations.

Core Competencies

• Strategic and operational leadership
• Infrastructure and cybersecurity management
• ERP and enterprise systems expertise
• Project and change management
• Analytical problem solving
• Business partnership and stakeholder management
• Vendor and contract management
• Financial and budget management
• Innovation and continuous improvement
• Accountability and professionalism

Working Environment

• Fast‑paced operational and corporate environment
• Collaboration with executive and operational leadership teams
• Management of multiple concurrent initiatives
• Combination of strategic planning and hands‑on leadership
• Occasional travel to operational sites as required

Why This Role Matters

The Director, Information Technology plays a critical role in enabling operational excellence, cybersecurity resilience, enterprise scalability, and digital transformation across YORK1. By modernizing infrastructure, optimizing systems, advancing AI capabilities, and strengthening governance and security practices, this role directly supports operational efficiency, risk mitigation, data‑driven decision‑making, and long‑term organizational growth.