Director, Information Technology

YORK1•Toronto, ON

17h•Hybrid

About The Position

At YORK1, technology plays a critical role in enabling operational excellence across field operations, fleet management, customer service, compliance, reporting, and enterprise growth initiatives. Reporting to the President & CEO, the Director, Information Technology will lead the modernization and optimization of the organization’s IT environment while supporting business continuity, operational efficiency, enterprise integrations, and long-term growth. This role will also play a key leadership function in advancing cybersecurity maturity, ERP transformation initiatives, cloud infrastructure, and technology governance across the organization. The Director, Information Technology is a strategic and hands-on leadership role responsible for overseeing the organization’s enterprise technology environment, including infrastructure, cybersecurity, ERP systems, integrations, disaster recovery, operational technologies, and digital transformation initiatives. This role ensures that technology platforms are secure, scalable, resilient, and aligned to YORK1’s operational and business priorities. This role will also lead YORK1’s evolving AI and intelligent automation strategy by identifying, evaluating, and implementing practical AI-enabled solutions that improve operational efficiency, reporting accuracy, workforce productivity, predictive analytics, customer experience, and business decision-making across the organization.

Requirements

7–10+ years of progressive leadership experience in Information Technology, enterprise systems, infrastructure management, or cybersecurity leadership roles.
Experience leading enterprise IT operations within industrial, environmental services, transportation, logistics, construction, manufacturing, or operationally intensive industries preferred.
Proven experience leading ERP implementations, migrations, enterprise integrations, and digital transformation initiatives.
Experience overseeing cybersecurity programs, disaster recovery planning, infrastructure modernization, and cloud environments.
Experience managing third-party vendors, managed service providers, and enterprise technology partners.
Experience evaluating or implementing AI-enabled technologies, automation platforms, analytics solutions, or intelligent business systems preferred.
Experience supporting enterprise data strategy, reporting modernization, or business intelligence initiatives considered an asset.
Demonstrated success leading cross-functional technology projects in fast-paced operational environments.
Strong knowledge of enterprise infrastructure, cloud technologies, networking, cybersecurity frameworks, and systems architecture.
Experience with ERP systems, CRM platforms, enterprise integrations, and operational technologies.
Strong understanding of cybersecurity best practices, vulnerability management, disaster recovery, and business continuity planning.
Knowledge of Microsoft environments, cloud platforms, virtualization, backup technologies, and enterprise applications.
Strong understanding of IT governance, risk management, data privacy, and compliance frameworks.
Understanding of AI technologies, workflow automation tools, business intelligence platforms, and data analytics capabilities.
Familiarity with governance, compliance, cybersecurity, and operational considerations related to AI adoption within enterprise environments.
Experience supporting infrastructure resiliency, operational uptime, and enterprise scalability initiatives.
Strategic and operational leadership
Infrastructure and cybersecurity oversight
ERP and enterprise systems expertise
Project and change management capability
Strong analytical and problem-solving skills
Business and operational alignment
Communication and stakeholder management
Vendor and partner management
Financial and budget management acumen
Innovation and continuous improvement mindset
Accountability, professionalism, and operational discipline
Ability to lead in a fast-paced, evolving environment

Responsibilities

Support and execute YORK1’s enterprise IT strategy aligned to operational and business objectives.
Lead enterprise-wide digital transformation initiatives focused on automation, operational efficiency, reporting capabilities, and system scalability.
Partner with operational leadership to identify technology solutions that improve field operations, customer experience, compliance, and data visibility.
Evaluate emerging technologies, AI-enabled tools, and operational technologies that support continuous improvement and business growth.
Develop technology roadmaps that align infrastructure, applications, cybersecurity, and enterprise systems with organizational priorities.
Lead the evaluation, implementation, and governance of AI-enabled technologies and intelligent automation solutions across operational and corporate functions.
Identify opportunities to leverage AI, machine learning, predictive analytics, and workflow automation to improve operational efficiency, reporting, scheduling, customer experience, and decision-making.
Partner with operational leaders to prioritize AI use cases that create measurable business value and productivity improvements.
Establish governance, security, and acceptable-use frameworks for AI technologies across the organization.
Oversee the performance, reliability, scalability, and security of all IT infrastructure including networks, servers, cloud environments, telecommunications, and end-user computing environments.
Lead infrastructure modernization initiatives including cloud migrations, system upgrades, network optimization, and enterprise platform enhancements.
Manage and optimize enterprise business systems including ERP, CRM, operational software, fleet technologies, reporting platforms, and operational technologies.
Lead ERP migration, implementation, enhancement, and integration initiatives across the organization.
Ensure enterprise applications and operational systems are effectively integrated to support business efficiency, data integrity, and reporting capabilities.
Establish infrastructure standards, lifecycle management practices, and governance controls for enterprise technology environments.
Assess and manage cybersecurity, privacy, and operational risks associated with AI technologies, automation platforms, and third-party integrations.
Establish governance standards related to AI usage, data protection, ethical use, and enterprise compliance requirements.
Lead the organization’s cybersecurity strategy, governance framework, and security operations to protect enterprise systems, infrastructure, and data assets.
Develop and maintain cybersecurity policies, standards, controls, and incident response protocols aligned with industry best practices.
Oversee vulnerability management, security monitoring, endpoint protection, access controls, and risk mitigation initiatives.
Ensure business continuity through robust disaster recovery planning, backup management, infrastructure resiliency, and recovery testing.
Partner with external cybersecurity providers and internal stakeholders to proactively manage operational technology and enterprise security risks.
Ensure compliance with applicable cybersecurity, privacy, and regulatory requirements.
Lead technology risk assessments, penetration testing coordination, and remediation planning.
Lead enterprise ERP initiatives including migrations, implementations, enhancements, optimization, and post-go-live stabilization.
Oversee enterprise systems integrations between operational platforms, finance systems, HRIS, CRM, fleet technologies, and third-party applications.
Manage cross-functional technology projects ensuring alignment to operational priorities, budgets, timelines, and business outcomes.
Drive standardization of enterprise processes, data governance, reporting structures, and system utilization across the organization.
Partner with operational and finance leadership to improve reporting accuracy, business intelligence, and data accessibility.
Lead initiatives that leverage AI-driven reporting, automation, and predictive analytics capabilities within ERP and enterprise business systems.
Support intelligent workflow automation initiatives that improve operational scalability and reduce manual processes.
Oversee day-to-day IT operations, service delivery, helpdesk support, and user experience across all business locations.
Establish and monitor service standards, escalation processes, and performance metrics for IT support delivery.
Ensure timely resolution of technology-related issues to minimize operational disruption.
Continuously improve IT operational processes, system uptime, service responsiveness, and overall technology effectiveness.
Support operational sites and business leaders with technology planning, deployment, and issue resolution.
Manage relationships with external vendors, managed service providers, cybersecurity partners, consultants, and technology providers.
Negotiate software licensing agreements, support contracts, service level agreements, and vendor renewals.
Evaluate vendor performance, cost effectiveness, and alignment to operational and strategic objectives.
Oversee procurement, deployment, and lifecycle management of technology assets and enterprise platforms.
Develop and manage the annual IT operating and capital budgets.
Monitor technology expenditures and identify opportunities for cost optimization and operational efficiency.
Prioritize technology investments based on business value, infrastructure risk, cybersecurity exposure, and operational impact.
Support long-term infrastructure and systems planning to ensure scalability and sustainability.
Lead, mentor, and develop the IT team while fostering a culture of accountability, collaboration, innovation, and continuous improvement.
Establish clear performance expectations, development plans, and succession planning within the IT function.
Promote strong cross-functional partnerships between IT and operational leadership teams.
Act as a trusted advisor to business leaders on technology strategy, risk management, and operational enablement.