Deputy Chief Technology Officer, Digital Business and Enterprise Applications – City of Toronto

About the City of Toronto

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.

The Opportunity

Toronto is a global leader in technology, finance, film, music, culture, and innovation, consistently ranking 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. Lead the delivery of digital transformative technologies through modern enterprise capabilities with resilience across public and divisional-facing platforms
2. Deliver User-Centric Solutions: Provide end-to-end solutions that provide ease of use and are accessible and flexible in serving the needs of the public
3. Harness data to drive action and engagement across platforms, processes and experiences
4. Empower Stakeholders: Engage and empower teams to foster a culture of agility and innovation while driving platform/product roadmaps

Reporting directly to the Chief Technology Officer, the Deputy Chief Technology Officer, Digital Business and Enterprise Applications, brings hands-on experience with Agile delivery, DevOps, and building modern, scalable digital systems.

You’ll be leading the development of digital platforms that support both internal operations and the services residents rely on every day, while leading the platform and architecture roadmap to deliver on our vision.

Beyond digitizing our services, you will shape the City’s digital delivery approach, drive enterprise transformation, and embed a strong culture of excellence and continuous improvement. Your work will improve the digital experience and journey for both staff and the residents of Toronto.

Ideal Candidate Profile

The successful candidate will be a visible, hands-on leader with a deep understanding of delivery digital transformation at scale.

They will bring empathy, curiosity and a collaborative spirit, with the ability to engage deeply with both technical and non-technical teams, ask the right questions and build trust across a large, complex organization.

This role requires more than setting direction; it calls for someone who actively shapes the path forward with their teams, translates strategy into action, clarifies expectations and ensures real progress on transformation initiatives.

This is not a traditional, policy-focused leadership role. It is executional and delivery-driven.

The ideal candidate is politically astute, comfortable in high-accountability environments and skilled at aligning with peers across departments while navigating sensitivities around contracts, governance and council priorities.

They must be able to coach cross-functional teams, develop delivery capability and shift the culture from a transactional service model to one of shared ownership.

This is a role for a seasoned leader who leads by doing, builds credibility quickly and demonstrates what is possible through both vision and action.

The Deputy CTO will have significant autonomy to shape priorities and lead change, supported by a talented team of over 200 technology professionals.

This is a senior leadership role with broad influence across the organization and the opportunity to directly impact service delivery for millions of residents.

Key Responsibilities

Digital Delivery and Agile Systems Leadership:

• Drive the design, build, and continuous delivery of digital systems and platforms that power core city services.
• Champion Agile, DevOps, solution design and development capability to accelerate delivery while building team capabilities, modern development practices and platform maturity.
• Build out and execution of a City-wide enterprise digital roadmap across key customer touchpoints for key services, with the goal of digitizing key touchpoints.
• Co-leadership of programs with key divisions (Customer Experience, Housing, Parks and Recreation, etc.) with the goal of driving efficiency and enhanced experience for the public.
• Oversee architecture, solution design, and platform governance across the TSD division.

Modernization, Continuous Improvement and Enterprise Architecture:

• Lead the strategy, delivery, and implementation of large-scale corporate programs, including digital services, divisional application development, public-facing services, solution architecture and design services.
• Works across divisions to adopt modern delivery practices to deliver with agility and efficiency, including continuous development/improvement tools, adoption of modern platform development, quality engineering, security and release management practices.
• Drive rapid response programs aligned to Council and Mayoral priorities, advancing capabilities across teams and divisions to deliver with speed and agility.
• Lead change across the way we work; develop new standards across platforms, delivery capabilities, and lead the evolution of Technology Services architecture to serve emerging needs.

Strategic Partnerships and Leadership:

• Collaborate across City divisions and Council to align digital priorities with the needs of the public and strategic business goals.
• Co-leads key division and platform roadmaps, inclusive of application lifecycle management, modernization and decommissioning plans.
• Collaborates with finance and procurement teams to optimize vendor relationships and negotiate favourable contracts for the City of Toronto.
• Works closely with the CTO, peers, and City leadership to identify and capitalize on opportunities where technology can add value to support program operations and strategic objectives.

Culture and Team Leadership:

• One Team: Cultivating a sense of unity where each member understands their purpose and impact.
• Performance and Resiliency: Building high performance and resiliency through modelling standards, trust, transparency, and respect.
• Creativity and Innovation: Encouraging creativity and innovation by welcoming diverse perspectives, promoting healthy debate, and questioning the status quo.
• Equity and Accountability: Respecting each other’s ideas and leaning into equity and accountability, creating a sense of independence and ownership.

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 technology teams in the delivery of large-scale enterprise applications through transformation stages to modern platforms, cloud-based technologies and digital programs.
• Proven track record of working with business partners in developing strategic, technology and user-centric programs through project and program delivery roadmaps.
• Experience in helping teams deliver enterprise and domain-level architecture planning programs while delivering solution design services to teams.
• Considerable experience leading a high-performing team through change, ensuring continued successful service delivery.
• Experience and knowledge of transforming teams into new ways of working across modern technologies (cloud, SAAS, AI) and methodologies (Agile/SAFE, CI/CD, DevOPS, etc.).
• Effective communication skills with the ability to communicate with both technical and non-technical stakeholders, senior leaders, and governing bodies.
• Proven success in managing large projects, development and support streams with a high degree of employee and stakeholder satisfaction.

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.

How to Apply

To apply to this exciting opportunity, email your resume to:
Marty Greenaway, Consultant
E: mgreenaway@feldmandaxon.com

The City of Toronto supports a hybrid work model for this position, with flexibility based on operational and leadership needs.