About the City of Toronto
The City of Toronto is the fourth-largest city in North America and the fourth-largest government in Canada, serving a highly diverse and multicultural population.
The broader municipal organization includes several agencies and corporations, such as the Toronto Police Service, Toronto Public Library, and the Toronto Transit Commission, which together support the delivery of essential public services across the city.
Toronto is consistently ranked among the world’s most livable cities and is home to more than 2.9 million people. Its diversity of communities, perspectives, and experiences is a defining strength and a key driver of its position as Canada’s leading economic engine and one of the most dynamic urban centres globally.
The Opportunity
Toronto stands as a global hub for technology, finance, film, music, culture, and innovation, consistently achieving top international rankings through sustained investment by government, residents, and the business community.
As the City advances its ambition to modernize services through strategic investment and disciplined execution, the Technology Services Division plays a critical enterprise role.
Working across all City divisions, agencies, boards, and corporations, the Division delivers complex, enterprise-wide programs that enable reliable, efficient, and citizen-focused outcomes.
As part of this continued evolution, the Division is strengthening its enterprise delivery capability through a centralized Program and Project Delivery, designed to drive consistency, accountability, and excellence across large-scale initiatives.
This transformation is anchored in four key priorities:
- Lead Enterprise Program Delivery: Execute large, multi-year, cross-divisional programs with a focus on predictability, transparency, and measurable outcomes.
- Modernize Delivery Practices: Enhance and standardize project and program management methodologies to improve speed, quality, and alignment in a highly regulated environment.
- Strengthen Governance and Investment Discipline: Ensure rigorous oversight of business cases, capital and operating budgets, and enterprise investment decisions.
- Enable Collaborative Execution: Foster strong partnerships across divisions and stakeholders, embedding a culture of shared accountability, adaptability, and continuous improvement.
Reporting directly to the Chief Technology Officer, the Deputy Chief Technology Officer, Program and Project Delivery, will bring deep experience leading large-scale enterprise programs within complex, matrixed organizations.
You will be accountable for establishing and overseeing a centralized PMO that supports multiple divisions and delivers critical initiatives, including the modernization of core business systems and the replacement of legacy platforms.
This role requires a structured, outcomes-driven leader who can operate effectively within formal governance and procurement frameworks while also advancing transformation in program delivery practices.
Beyond execution, you will play a pivotal role in shaping the City’s enterprise delivery model, elevating standards, strengthening vendor and partner management, and ensuring alignment between strategic priorities and program outcomes.
Through trusted relationships and strong influence, you will engage division leaders and stakeholders to enable the successful delivery of both funded and emerging initiatives.
Your leadership will be instrumental in ensuring the City’s most critical investments are delivered with discipline, transparency, and lasting impact for internal operations and the residents of Toronto.
Ideal Candidate Profile
The successful candidate will be a visible, hands-on enterprise leader with deep expertise in delivering large-scale programs through a centralized Project Management Office.
They will bring empathy, curiosity, and a highly collaborative leadership style, with the ability to engage effectively with technical and non-technical teams, ask incisive questions, and build trust within a large, complex organization.
This role requires more than directional leadership. It requires a leader who actively shapes execution alongside their teams, translating strategy into structured delivery, clarifying expectations, and ensuring consistent progress across complex, multi-year initiatives.
This is not a traditional, policy-focused leadership role. It is execution-focused and delivery-driven.
The ideal candidate is politically astute, comfortable operating in high-accountability environments, and skilled at aligning with peers across divisions while navigating sensitivities related to procurement, governance, funding, and Council priorities.
They will be capable of coaching cross-functional teams, strengthening enterprise delivery capability, and advancing a shift from siloed execution to coordinated, disciplined, and accountable delivery.
This is a role for a seasoned leader who leads from the front, builds credibility quickly, and demonstrates what is possible through structured execution and measurable outcomes.
The Deputy Chief Technology Officer, Program and Project Delivery, will have significant autonomy to set priorities and lead change, supported by a broad cross-functional team delivering critical initiatives across the City.
This senior leadership role offers enterprise-wide influence and the opportunity to directly shape how major programs are delivered, ensuring that investments translate into tangible improvements in City operations and for the residents of Toronto.
Key Responsibilities
Enterprise Program Delivery and PMO Leadership:
- Drive the planning, execution, and continuous delivery of large-scale, enterprise programs that support core City services.
- Champion modern project and program management methodologies to accelerate delivery while strengthening team capabilities, standardizing practices, and maturing enterprise PMO functions.
- Build and execute a city-wide enterprise delivery roadmap across key programs and initiatives, ensuring alignment with strategic priorities and measurable outcomes.
- Co-lead major initiatives with key divisions (e.g., Customer Experience, Housing, Parks and Recreation) to drive operational efficiency and enhance service delivery.
- Oversee program governance, delivery frameworks, and standards across the Technology Services Division.
Modernization, Continuous Improvement, and Delivery Excellence:
- Lead the strategy, delivery, and implementation of large-scale corporate programs, including enterprise system modernization, divisional initiatives, and business-critical platforms.
- Work across divisions to adopt modern, structured delivery practices that improve efficiency, predictability, and accountability, including standardized tools, reporting, and performance management.
- Drive priority programs aligned with Council and Mayoral direction, enabling teams and divisions to deliver with speed while maintaining governance and control.
- Lead transformation in how programs are delivered; establish enterprise standards, strengthen PMO capabilities, and evolve delivery models to meet emerging organizational needs.
Strategic Partnerships and Leadership:
- Collaborate across City divisions and Council to align program priorities with public needs and strategic business objectives.
- Co-lead enterprise program roadmaps, including planning, sequencing, and execution of complex, multi-year initiatives.
- Collaborate with finance and procurement teams to oversee business cases, manage budgets, and optimize vendor relationships and contracts.
- Work closely with the CTO, peers, and City leadership to identify and advance opportunities where strong program execution can drive operational and strategic impact.
Culture and Team Leadership:
- One Team: Cultivating a sense of unity where each member understands their role in successful program delivery and enterprise outcomes.
- Performance and Resilience: Building high performance and resilience through clear expectations, disciplined execution, trust, transparency, and respect.
- Creativity and Innovation: Encouraging innovation in delivery approaches by welcoming diverse perspectives, promoting healthy challenge, and improving how work gets done.
- Equity and Accountability: Fostering a culture of ownership, accountability, and inclusion, where teams are empowered to deliver results within a structured framework.
Required Skills, Qualities, and Experience
- Post-secondary education in business administration, engineering, computer science, information technology, or an equivalent combination of education and experience.
- Must have 10+ years of experience leading teams in the delivery of large-scale, enterprise programs through complex, multi-year initiatives, including the modernization and implementation of business-critical systems.
- Proven track record of working with business partners to develop and execute strategic, enterprise-wide programs through structured project and program delivery roadmaps.
- Experience establishing and leading PMO functions, including governance frameworks, delivery standards, reporting structures, and portfolio management practices.
- Considerable experience leading high-performing teams through change, ensuring consistent, disciplined execution and successful program outcomes.
- Experience driving the adoption of modern delivery methodologies (e.g., Agile, SAFe, hybrid models) and improving delivery maturity across large, complex organizations.
- Strong financial and operational acumen, including experience in business case development, capital and operating budget management, and investment prioritization.
- Experience managing vendors and external partners, including procurement processes, contract negotiation, and performance management.
- Effective communication skills, with the ability to engage both technical and non-technical stakeholders, senior leaders, and governing bodies.
- Proven success in leading large, complex programs and portfolios, with a high degree of employee and stakeholder satisfaction.
The City of Toronto supports a hybrid work model for this position, with flexibility based on operational and leadership needs.
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 it 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.
How to Apply
To apply to this exciting opportunity, email your resume to:
Marty Greenaway, Consultant
E: mgreenaway@feldmandaxon.com
This job posting is for an existing position with the City of Toronto.
We do not use artificial intelligence (AI) tools to screen, assess, or select applicants at any stage of the hiring process.
All applications will be reviewed and evaluated by the Feldman Daxon team.