Director, Enterprise AI Strategy & Transformation
Job Location:
North York - Canada
Monthly Salary:
Not provided by the employer
Posted:
1 October 2026 (8 days ago)
Application Deadline:
29 December 2026
Vacancies:
1 Vacancy
Job Summary
JOB PURPOSE
Reporting to the Chief Financial Officer the Director Enterprise AI Strategy & Transformation leads the development and execution of the organizations enterprise AI strategy and transformation agenda to drive measurable business value productivity operational efficiency innovation and informed decision-making. The role serves as the organizations AI subject matter expert and enterprise coordinating point providing strategic guidance on AI opportunities investments governance risk technology adoption and value realization.
The Director partners with business and functional leaders to identify prioritize and implement AI and intelligent automation opportunities aligned with organizational objectives and financial goals. The role initially focuses on leveraging AI to enhance financial and operational performance including forecasting reporting analysis productivity workflow efficiency cost management and decision-making with successful capabilities and practices progressively expanded across other functions. The Director oversees the enterprise AI portfolio and lifecycle from opportunity assessment and business case development through solution selection implementation adoption benefits realization ongoing monitoring and retirement.
KEY DUTIES AND RESPONSIBILITIES
AI Strategy Portfolio & Value Management
Reporting to the Chief Financial Officer the Director Enterprise AI Strategy & Transformation leads the development and execution of the organizations enterprise AI strategy and transformation agenda to drive measurable business value productivity operational efficiency innovation and informed decision-making. The role serves as the organizations AI subject matter expert and enterprise coordinating point providing strategic guidance on AI opportunities investments governance risk technology adoption and value realization.
The Director partners with business and functional leaders to identify prioritize and implement AI and intelligent automation opportunities aligned with organizational objectives and financial goals. The role initially focuses on leveraging AI to enhance financial and operational performance including forecasting reporting analysis productivity workflow efficiency cost management and decision-making with successful capabilities and practices progressively expanded across other functions. The Director oversees the enterprise AI portfolio and lifecycle from opportunity assessment and business case development through solution selection implementation adoption benefits realization ongoing monitoring and retirement.
KEY DUTIES AND RESPONSIBILITIES
AI Strategy Portfolio & Value Management
- Develop and maintain the enterprise AI strategy operating model portfolio and roadmap aligned with corporate objectives and financial goals.
- Identify evaluate and prioritize AI opportunities based on strategic alignment business value cost complexity data readiness risk and organizational readiness.
- Develop business cases investment recommendations and implementation roadmaps including build buy configure or partner options.
- Establish performance measures baseline metrics and value-realization frameworks to track AI adoption ROI productivity cost savings revenue impact and other business outcomes.
- Provide executive leadership with visibility into AI investments performance realized benefits opportunities and risks.
AI Solution Development & Implementation
- Lead the evaluation design development and deployment of AI solutions across enterprise productivity function-specific applications intelligent automation advanced AI and emerging agentic capabilities.
- Partner with business units and end users to identify opportunities develop practical AI-enabled solutions and improve processes and ways of working.
- Oversee AI pilots proofs of concept and enterprise implementations through the full lifecyclefrom opportunity identification and feasibility through deployment adoption benefits realization monitoring and retirement.
- Coordinate with Cybersecurity Human Resources and other stakeholders to ensure solutions are appropriately designed implemented adopted and measured.
- Assess solution performance and recommend whether initiatives should be scaled enhanced consolidated paused or retired based on business value adoption cost and risk.
- Establish and maintain enterprise AI governance frameworks policies standards controls and risk-based processes to support responsible AI adoption.
- Ensure AI initiatives are appropriately assessed for cybersecurity privacy data intellectual property legal ethical third-party model and business continuity risks.
- Maintain an enterprise inventory of approved AI technologies platforms models agents and material use cases with appropriate review approval testing human oversight monitoring and escalation requirements.
- Ensure data quality classification access security information governance and regulatory requirements are addressed before AI solutions are deployed.
- Monitor the evolving AI landscape regulatory expectations and associated risks and update governance practices as required.
- Lead enterprise AI literacy adoption and change-management initiatives across executives leaders employees technical teams and advanced AI users.
- Develop and deliver role- and function-specific training guidance and resources to promote effective and responsible use of AI.
- Serve as the enterprise resource for AI strategy best practices use-case guidance and adoption support.
- Measure AI utilization adoption training effectiveness employee feedback and business outcomes to continuously improve AI enablement.
- Coordinate internal subject matter experts technology teams business stakeholders and external partners to support successful AI adoption
- Evaluate AI technologies vendors consultants platforms and implementation partners against business requirements value security architecture scalability risk and total cost of ownership.
- Manage AI technology and vendor relationships to ensure service quality effective implementation and value realization.
- Maintain oversight of the enterprise AI technology portfolio to identify duplicate capabilities unnecessary licensing overlapping solutions and opportunities for consolidation.
- Monitor emerging AI technologiesincluding generative AI large language models predictive AI intelligent automation computer vision and agentic AIand assess their practical business applicability and potential value.
QUALIFICATIONS SKILLS AND EDUCATIONAL REQUIREMENTS
PHYSICAL DEMANDS AND WORKING CONDITIONS- Bachelors degree in Computer Science Data Science Information Technology Engineering Finance Business Administration or a related field; Masters degree preferred.
- Minimum seven (7) years of progressive experience in AI data analytics digital transformation automation technology or related fields including significant experience leading enterprise AI or generative AI adoption.
- Proven experience leading complex enterprise-wide AI or business transformation initiatives from strategy and business case development through implementation adoption scaling and measurable value realization.
- Strong business and financial acumen including experience with budgeting forecasting reporting business case development technology investment evaluation performance measurement and ROI.
- Strong knowledge of AI technologies including generative AI machine learning predictive analytics intelligent automation large language models AI agents and emerging AI capabilities with an understanding of data cybersecurity privacy and AI governance.
- Strong strategic thinking analytical communication stakeholder management project management and change management skills with the ability to translate complex technology into practical business solutions and influence cross-functional decisions.
- Strong technical and business judgment to evaluate AI solutions vendors risks data and technology dependencies and investment decisions. Professional certifications in AI analytics project management responsible AI or AI governance are considered an asset.
- Standard office setting - hybrid arrangement (4 days in-office)
- Fast paced office environment
- Travel expectations between facilities in Mississauga and North York
Required Experience:
Director