Career Opportunities: Head, Technology Delivery and Sustainment Operations (11542)

Career Opportunity

Are you an accountable leader with deep expertise in IT infrastructure, operations, and service delivery? Do you possess strong leadership and communication skills to guide high-performing teams and drive impactful outcomes? Are you committed to delivering critical initiatives while upholding the highest standards of performance and quality? If so, we have an exciting opportunity for you! 

The Information Technology Services (ITS) department at the TTC is seeking a Head, Technology Delivery and Sustainment Operations. 

What You Will Do

Reporting directly to the Chief Information Officer (CIO), the Head of Technology Delivery & Sustainment Operations will serve as a strategic partner and trusted advisor. You will be responsible for overseeing the seamless delivery, maintenance, and continuous improvement of the TTC’s technology infrastructure and services. Your leadership will ensure the performance, reliability, and sustainability of critical IT systems, while aligning technology initiatives with the organization’s strategic goals. 

In this role, you will be accountable for the full lifecycle of IT products—from initial concept through delivery and ongoing enhancement. You will develop and maintain product roadmaps aligned with the TTC’s strategic objectives, ensure the timely resolution of bugs and enhancement requests, and collaborate with cross-functional teams to identify and implement product improvements. You will also monitor and drive project timelines, budgets, and scope to ensure the successful and efficient delivery of IT solutions. 

You will manage the operation and maintenance of the TTC’s IT infrastructure to ensure high availability, performance, and scalability. This includes continuously assessing infrastructure efficiency, implementing best practices for system monitoring, disaster recovery, and data integrity, and leading capacity planning and resource allocation to meet current and future business needs. 

You will be accountable for delivering exceptional IT service to end users by establishing a single point of contact for IT services, maintaining an effective Service Desk and field services team, and overseeing the provisioning of end-user devices and software in compliance with security policies. You will optimize software provisioning, hardware lifecycle management, and inventory control processes, while regularly evaluating and enhancing service performance to ensure high levels of user satisfaction. 

As a people leader, you will be responsible for building, guiding and leading a high-performing IT delivery organization. This includes exemplifying and fostering a culture of collaboration, accountability, and continuous improvement; identifying skill gaps and implementing training programs; and clearly defining roles, responsibilities, and performance expectations to drive team success. You demonstrate agile leadership by proactively engaging and taking hands-on action during critical project phases or high-impact initiatives. 

You will also demonstrate behaviors that support diversity, inclusion, and a respectful work and service environment that is free from discrimination and harassment. You will help remove barriers and accommodate employees and customers (within your area of responsibility) in accordance with the TTC’s commitments and obligations under the Ontario Human Rights Code (OHRC), the Accessibility for Ontarians with Disabilities Act (AODA), and TTC policies. 

Participate in the TTC Customer Service Ambassador Program, contributing to a culture of service excellence across the organization. 

What Skills Do You Bring ?

What Qualifications Do You Bring ?

• You are a driven and strategic technology leader with extensive knowledge of information technology and business strategy. You bring a proven track record of developing and executing plans that align technology solutions with organizational goals. Your experience includes managing detailed budgets, developing comprehensive project plans, and implementing effective risk management strategies.

• You have successfully led complex, high-impact projects to completion, demonstrating a deep understanding of solution development methodologies and quality management practices. Your strong business relationship management skills enable you to build trust and alignment across diverse stakeholder groups. 

• As a people leader, you lead by example and are skilled at developing processes and procedures that gain the support and buy-in of your teams. You possess a detailed understanding of industry-standard Key Performance Indicators (KPIs) and know how to implement and manage them to drive performance.

• Your analytical, communication, and interpersonal skills are exceptional, and you bring above-average organizational and problem-solving abilities to manage relationships with department heads and executive leadership. You are also adept at motivating and leading staff, and you provide effective senior leadership to steering committees and cross-functional teams.

• You either possess or are able to rapidly acquire a comprehensive understanding of the Ontario Human Rights Code and related accessibility requirements for both employees and passengers. 

• You have or can quickly acquire a strong understanding of TTC and ITS Department policies and procedures.

• You have extensive knowledge of the TTC’s computer systems, hardware, software, and applications, and you stay current with industry trends and emerging technologies.

• You bring several years of progressive leadership experience in solution delivery roles such as Project/Program Management, Application Development, or Support Management.

• Your educational background including completion of a post-secondary education a related discipline (Computer Science, Business, or a related discipline) or a combination of education, training and experience deemed to be equivalent is integral and will contribute to the success in this role.

• Working knowledge of human rights legislation and corporate policies, including the Ontario Human Rights Code, Occupational Health and Safety Act, and applicable TTC policies including but not limited to Respect and Dignity and Workplace Violence is required. 

What We Offer

• Commitment to creating a diverse, equitable and inclusive culture that promotes a sense of belonging and represents and reflects the needs of the communities we serve.
• One of the great benefits of being a full-time TTC employee is becoming a member of the TTC defined pension plan.
• A comprehensive package that covers health, dental, vision and more.
• Support for professional development opportunities for all colleagues through a broad range of learning programs that include in-person and online training, leadership development, and support for colleagues’ well-being.
• A flexible, hybrid work approach that allows colleagues to find balance between their professional and personal lives and making the most of the benefits of working remotely and purpose-driven in-person collaboration opportunities. 

Commitment to EDI

The TTC is committed to upholding the values of equity, diversity, anti-racism and inclusion in the delivery of its services and in its workplaces. The TTC is committed to fostering a diverse workforce that is representative of the communities it serves at all levels of the organization and supports an inclusive environment where diverse employee and community perspectives and experiences bring value to the organization. The TTC encourages applications from all applicants, including members of groups with historical and/or current barriers to equity, including but not limited to, Indigenous, Black and racialized groups, people with disabilities, women and people from the LGBTQIA+ community. The TTC values and supports an inclusive and barrier-free recruitment and selection process. Accommodations for applicants are available upon request throughout the recruitment and selection process, including for those who identify as having a disability. Please contact Talent Management at (416) 393-4570. Any information received related to an accommodation will be addressed confidentially.
 

The TTC’s policy prohibits relatives of current TTC employees from being hired, assigned, transferred or promoted into positions, where there is a conflict of interest due to a relationship. Should you be selected for an interview, you will be required to disclose the name, relationship and position of any relative who is a current TTC employee. 
 

 
We thank all applicants for their interest but advise only those selected for an interview will be contacted.