About the City of Toronto

The City of Toronto is Canada’s largest city, the fourth largest in North America, and home to a diverse ppulation of approximately 2.8 million people. A global centre for business, finance, arts, and culture, Toronto is recognized internationally for its economic vitality, inclusivity, and quality of life. Consistently ranked among the world’s most livable cities, Toronto offers a dynamic urban environment with vibrant neighbourhoods, strong civic institutions, and a commitment to innovation, sustainability, and public service.

About the Role

Reporting to the Deputy City Manager, the General Manager, Transportation Services will provide strategic and operational leadership for one of Canada’s largest and most complex urban transportation systems. Responsible for Toronto’s streets, sidewalks, bridges, traffic operations, signals, signage, and right-of-way management, this role sits at the centre of how the city moves. At a pivotal time of transformation, the General Manager will shape policy, set strategy, and implement best-in-class practices that enhance safety, service delivery, and customer experience city-wide. As a trusted advisor and decisive leader, you will oversee significant budgets, performance metrics, and labour relations while driving innovation and ensuring Toronto remains a leader in progressive, responsive transportation services.

Key Responsibilities

Strategic Leadership & Governance

• Sets the long-term vision and strategic direction for Transportation Services, aligning divisional priorities with Council and City objectives
• Serves as a trusted advisor to the Mayor, Council, Standing Committees, and Task Forces
• Builds strong relationships across City divisions and with external government, private, and community partners

Policy, Performance & Financial Stewardship

• Oversees the policy framework, regulations, and standards governing transportation services city-wide
• Leads multi-year financial planning, budget development, and forecasting to ensure alignment with Council direction
• Establishes performance metrics, benchmarks, and reporting systems to drive accountability and continuous improvement

Operational Excellence & Safety

• Ensures Toronto’s transportation infrastructure, roads, bridges, sidewalks, traffic systems, and right-of-way, is safe, reliable, and cost-effective
• Oversees traffic and road operations to deliver accessible, efficient, multi-modal, and environmentally responsible services
• Champions compliance with the Occupational Health and Safety Act, embedding safety as a top organizational priority

People, Change & Collaboration

• Leads and develops a large, unionized workforce through periods of change, fostering high performance and resilience
• Strengthens labour relations through effective consultation, collective agreement compliance, and dispute resolution
• Promotes collaboration across the City to drive service improvements, efficiencies, and shared success

Qualifications

• Seasoned executive leader with progressive senior management experience in large, complex public or private sector organizations, leading multi-functional operations and diverse stakeholders
• Strategic and politically astute, with a strong understanding of public-sector governance and the role of professional advice in informing Council decision-making
• Strong operational and financial acumen, including expertise in policy and program development, budgeting, organizational planning, and performance management
• Trusted people leader and communicator, known for sound judgment, high ethical standards, effective labour and employee relations, and a commitment to health, safety, and organizational excellence

To apply for this key role, please fill out the application link below.

Application deadline: May 29, 2026

AI will not be used in the candidate screening process.

The posting for this position is for an existing vacancy.

To learn more information, visit our website at https://phelpsgroup.ca/

The City of Toronto is an equal opportunity employer. In accordance with the Accessibility for Ontarians with Disabilities Act, 2005, upon request, accommodation will be provided by both Phelps and the City of Toronto throughout the recruitment, selection and/or assessment process.