PROJECT DIRECTOR BUSINESS TRANSFORMATION (Enterprise Data & Artificial Intelligence)

• Job ID: 58268
• Job Category: Project Management
• Division & Section: Technology Services, Office of the Chief Technology Officer
• Work Location: Metro Hall, 55 John St. Toronto, ON, M5V 3C6
• Job Type & Duration: Full-time, Temporary Vacancy for 24 Months
• Salary: $142,104-$189,918
• Shift Information: Monday to Friday, 35 hours per week
• Affiliation: Non-Union
• Number of Positions Open: 1
• Posting Period: 23-JUL-20205 to 30-JUL-2025

The City of Toronto is the fourth largest city in North America and the fourth largest government in Canada, with a highly diverse and multicultural population. In addition, the City of Toronto has several agencies and corporations including the Toronto Police Service, Toronto Public Library, and the Toronto Transit Commission, which make up the broader municipal organization.

Consistently ranked one of the world’s most livable cities, Toronto is home to more than 2.9 million people whose diversity and experiences make this great city Canada’s leading economic engine and one of the world’s most diverse and livable cities.

Toronto is a global leader in technology, finance, film, music, culture and innovation, and consistently places at the top of international rankings due to investments championed by its government, residents and businesses.

In its pursuit of modernizing City services through strategic investment, digital transformation, and a culture of innovation, the Technology Services Division collaborates with all City Divisions, agencies, boards and corporations to deliver client centric business solutions and secure, reliable IT infrastructure.

Embarking on a transformative journey, the Technology Services Division is reshaping its culture and service delivery approach, focusing on four key priorities:

1. Build Resilient Foundations: Establish a robust, reliable, and secure technology infrastructure.
2. Deliver User-Centric Solutions: Provide enterprise-grade modern solutions with a focus on user experience.
3. Harness Data Power: Utilize data to drive operational processes and informed decision-making Citywide.
4. Empower Stakeholders: Engage and empower stakeholders to foster a culture of agility and innovation.

Position Summary

The City of Toronto is seeking a hands-on, strategic leader to drive the enablement of data and artificial intelligence (AI) technologies that enhance public service delivery and organizational performance. As Project Director, Business Transformation (Enterprise Data & Artificial Intelligence), you will lead transformative initiatives that embed data and AI into the fabric of City operations, empowering divisions to leverage innovative technologies in a complex, matrixed environment.

Reporting to the Director, Enterprise Data & Artificial Intelligence, you will provide operational leadership and strategic guidance to build and grow a dedicated AI enablement team - focused on optimizing AI & Data programs and tools, aligning structures with strategic goals, and building a culture of continuous improvement.

Specifically, you will provide leadership in the areas of:

Strategic Leadership & Organizational Transformation

• Provide strategic direction for the transformation, integration, and reorganization of divisional service delivery, ensuring alignment with organizational goals and the City’s broader data and AI strategy.
• Develop and implement functional policies and programs that significantly enhance business performance, grounded in long-term planning and future-state operating models.
• Lead the development and implementation of project management strategies and methodologies based on international best practices, ensuring successful delivery of transformation initiatives related to AI, digital modernization, and data enablement.

Team & People Leadership

• Direct, through subordinate management, all activities of a high-performing and diverse team, clearly delegating authority and supporting accountability at all levels.
• Recruit and manage divisional teams responsible for coordinating and delivering transformation strategies, ensuring access to the tools, resources, and capabilities needed to support success.
• Motivate and lead a multidisciplinary workforce, fostering effective teamwork and a culture of continuous learning, innovation, and collaboration.
• Provide guidance and direction to staff and management in applying sound program management practices to improve service delivery.

Governance, Change Management & Stakeholder Engagement

• Guide the development and implementation of comprehensive change management strategies, including communications, training, staff engagement, and stakeholder buy-in.
• Collaborate with the Director, Enterprise Data & AI, and other senior leaders, including the Division Head, Executive Team, and Steering Committee, to ensure project alignment with enterprise-wide priorities.
• Provide regular updates and reports to the Steering Committee and senior leadership on project status, risks, issues, deliverables, and milestones.
• Establish and maintain governance and accountability frameworks that reflect transparency, fairness, and effective decision-making throughout project lifecycles.
• Navigate complex stakeholder environments—including unionized settings, multi-agency partnerships, and political contexts—while resolving sensitive and high-stakes labour relations matters when required.

Performance Management, Financial Oversight & Integration

• Champion continuous improvement through rigorous analysis and the application of data-informed decision-making across all aspects of divisional operations.
• Oversee budget planning and administration for the transformation team, ensuring fiscal responsibility and that expenditures remain within approved limits.
• Lead integration initiatives from conception through implementation, including process mapping, risk and financial analysis, resource planning, contract management, and performance evaluation.
• Foster an outcome-driven organizational culture that prioritizes excellence in public service, the integration of AI and data innovation, and the measurable enhancement of City programs.

Key Qualifications:

1. University degree in Computer Science, Data Science or a related discipline, with extensive experience in a complex organizational environment, or equivalent combination of education and experience. Knowledge or certification in data analytics, AI, or cloud technologies (e.g., AWS, Azure, GCP) is an asset.
2. Extensive experience tracking and delivering complex, multi-stakeholder projects on time and within scope, including planning, execution, and reporting. Experience using project management tools (e.g., MS Project, JIRA, Trello) is preferred.
3. Extensive experience designing and leading educational programs focused on improving organizational literacy in data governance, AI ethics, and related technologies.
4. Experience leading educational and stakeholder-focused initiatives (e.g., workshops, training sessions) that support organizational goals related to data and AI.
5. Extensive experience collaborating and consulting with senior executives, technical teams, and external partners in a large-scale or municipal setting to achieve strategic goals.
6. Strong business writing and presentation skills, with the ability to develop clear, concise reports, briefing notes, and executive presentations tailored to various audiences.
7. Demonstrated ability to lead change initiatives, adapt to rapidly shifting priorities, and operate effectively in complex, ambiguous environments.
8. Exceptional ability to build and sustain relationships across various stakeholder groups, fostering teamwork and collaboration in a diverse, multi-stakeholder environment.
9.  Strong critical thinking, judgment, and political acumen to manage issues, resolve conflicts, and negotiate consensus in complex scenarios.
10. Knowledge of municipal government operations, approval processes, political structure, and experience with data governance, AI systems, and related emerging technologies.
11. Ability to support the Toronto Public Service values to ensure a culture that champions equity, diversity and respectful workplaces.
     

Why You Will Love Working Here

• We recognize the need for flexibility and offer a hybrid working environment that will provide you with an appropriate work-life balance required to thrive in today’s fast paced world.
• A strong benefits package which includes competitive salaries, vacation and other unique offerings.
• We offer an excellent defined benefit pension plan bringing added value to our overall compensation package through OMERS.
• We support ongoing learning and development and offer educational opportunities with tuition subsidies.
• Opportunities to join and take an active role with City’s Communities of Inclusions comprised of employees who share a common identity, lived experience and/or set of interest and support each other’s professional development, sense of belonging and promote a culture of inclusion.

Equity, Diversity and Inclusion

The City is an equal opportunity employer, dedicated to creating a workplace culture of inclusiveness that reflects the diverse residents that we serve. Learn more about the City’s commitment to employment equity.

Accommodation

The City of Toronto is committed to creating an accessible and inclusive organization. We are committed to providing barrier-free and accessible employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Should you require Code-protected accommodation through any stage of the recruitment process, please make them known when contacted and we will work with you to meet your needs. Disability-related accommodation during the application process is available upon request. Learn more about the City’s Hiring Policies and Accommodation Process.