Executive Superintendent, Technology, Data, and Strategic Transformation & Chief Information Officer, TCDSB

Job Location
Toronto Catholic District School Board
Description-Job Posting

Transforming the world through witness, faith, innovation, and action: The Toronto Catholic District School Board (TCDSB), Canada’s largest publicly funded Catholic school board, is an inclusive learning community rooted in the love of Christ. We serve students from diverse cultural, linguistic, and ethnic backgrounds and are proud to be a significant part of the fabric of publicly funded Catholic education in the Province of Ontario.

Working in partnership with parents, teachers, unions, associations, the Archdiocese of Toronto, and the wider community, the TCDSB educates students to their full academic, social, physical and spiritual potential in an inclusive learning community imbued with Catholic faith. With a long and distinguished history of providing excellence in Catholic education for the Toronto community, the TCDSB serves more than 84,000 students, 14,000 staff, 201 schools in this city.

With the upcoming departure of the current (Acting) Executive Superintendent, Technology, Data, and Strategic Transformation & CIO (“Executive Superintendent”), the TCDSB seeks a visionary leader to support the growth and success of its students, staff, and communities, and effectively meet the challenges of education today and into the future.

Responsible to the Board of Trustees through the Associate Director, Corporate Services, Chief Commercial Officer, the Executive Superintendent serves as TCDSB’s Chief Information Officer and is responsible for advancing the role of technology and data in the fulfillment of the mission of Toronto Catholic District School Board, providing executive leadership for system-wide modernization focused on both business and academic processes and practices through a technology and data-driven lens.

The Executive Superintendent will work closely with the Board of Trustees to meet the overall needs of the organization and act as a key advocate for the TCDSB with external partners such as, but not limited to, the provincial and federal governments and associated agencies, local municipalities, and other broader public sector organizations throughout Ontario and Canada.

As a member of Director’s Council, the Executive Superintendent Technology, Data, Strategic Transformation will inform the strategic direction and leadership of all information and communications technology operations, data privacy and security, admissions process, enrollment data and reporting, records, and overall technology adoption.

The ideal candidate will bring a combination of strategic leadership and oversight of all technology, data, and innovation supporting both pedagogy and infrastructure, as well as leadership for system-wide transformation projects such as the implementation of a new Student Information System, and implementation of new HR and Finance systems. With high emotional intelligence and a track record of success in implementation and leading through change, the preferred candidate is a champion of innovation, with a passion for Catholic education and TCDSB’s vision.

Major Responsibilities – Technology, Data, and Information:

Strategic leadership and oversight of all technology, data, and innovation supporting both pedagogy and infrastructure. This individual is a leader of leaders, inspiring, encouraging, and supporting Superintendents and school Principals. With a focus on supports and structures that wrap around every student, the Executive Superintendent recognizes the classroom teacher as having the greatest impact on student achievement, and strategically supports tools, technology, and practices that enable students to thrive in the existing digital world.

  • Demonstrate a commitment to the preservation and strengthening of publicly funded Catholic education.
  • Provide strategic leadership in the review, implementation and refinement of all information technology policies, structures, and initiatives.
  • Provide executive leadership on all data privacy, IT risk, and cybersecurity-related
  • Establish and maintain effective IT governance, data management, and decision-making processes in support of transformational changes.
  • Inform the strategic allocation of Board reserves to identify macro initiatives that enhance and sustain student achievement.
  • Guide, inspire and lead collaboration with other departments in support of the Board’s Multi-Year Strategic Plan and all related Information and Technology strategic plans.
  • Promote and develop effective partnerships with various internal and external stakeholders.
  • Be responsible for admission and enrollment processes, student data, and associated Ministry reporting.

Major Responsibilities – Strategic Transformation:

While maintaining leadership responsibilities for IT, data, and digital learning, the Executive Superintendent will provide project leadership for new and existing initiatives such as infrastructure improvements, SIS (Student Information System) transformation, and emerging issues and initiatives requiring executive project management acumen.

  • Provide leadership to system-wide transformation projects such as the implementation of a new Student Information System, and implementation of new HR and Finance systems and other initiatives as required.
  • In conjunction with other system leaders, lead the modernization of TCDSB offices and learning spaces fulfilling the TCDSB vision for the “Digitally Enabled School”.
  • Provide strategic input into system decision-making related to digital transformation and information technology through Director’s Council.
  • Support the development of leadership identification and development strategies.
  • Support the goals of the Multi-Year strategic plan and report on progress related to technology, data, digital strategy, and projects.
  • Leadership of strategic and organization-wide transformational projects as assigned.
  • Increase public confidence by providing innovative leadership and forward-looking strategy.

Major Responsibilities – Leadership:

With a focus on relationship building and leadership development, the Executive Superintendent leads a team of 125 IT professionals, strategic and creative leaders while supporting academic insight and innovation.

  • Foster and develop a working relationship with encourages employee commitment and motivation and ensure that appropriate authority is delegated to staff.
  • Coach/manage five direct reports who are leading cybersecurity, applications and IT, hardware and software.
  • Build an environment, inspiring a work culture of trust, accountability, empowerment, responsibility, and support.
  • Refine and implement an organizational structure for the Information Technology department that best enables TCDSB to provide services to support to students.
  • Ensure staff have access to resources, ongoing developmental feedback, continuing professional development and technical training.

Position Requirements

The ideal candidate will have:

  • A University degree in Information Technology or a related/relevant discipline.
  • A minimum of 10 years of proven leadership experience in information technology in large, complex, public and/or private organizations.
  • Experience leading large organizational transformation projects/initiatives and working with multiple stakeholders to manage associated organizational change.
  • Leading or being part of the senior team that has guided enterprise-wide projects from strategy to implementation with internal and external teams. Experience transforming ERP systems, Student Information System, Case Management Systems and/or large Records Management systems is an asset.
  • Experience in an education setting is an asset, along with an Ontario Supervisory Officer Certificate, or a commitment to obtain one in accordance with Ministry of Education within 2-3 years of starting the position.
  • Thorough knowledge of technologies supporting classroom and office environments, such as telecommunications networks, audio/visual systems, end-user computing devices, meeting and video conferencing systems, enterprise applications, learning management systems, and identity management.
  • A deep understanding of cloud technologies, data governance and analytics, data integration, and identity management practices.
  • Excellent understanding of project management principles and IT service management frameworks.
  • Well-developed change management skills. Comfortable building out new programs or ideas, effectively managing multiple priorities, and motivating teams to achieve deadlines.
  • Exceptional written and verbal communication skills, including the ability to translate technical subject matter into strong business cases with clear value propositions.
  • Proven success leading diverse teams of people, emphasizing accountability and empowerment; setting the tone for an open and supportive environment built on communication, teamwork, and trust.
  • Political acuity in order to advance agendas, collaborate with the Board of Trustees, government officials, and colleagues from other boards, etc.
  • Understanding of data privacy legislation and related requirements.
  • Demonstrated experience in managing and responding to complex data privacy and IT security matters including data breaches, cybersecurity matters, and associated policies.
  • Experience in public procurement practices including selecting, negotiating, and managing large vendor contracts.
  • Strong knowledge of current and emerging technologies in both administrative and instructional systems and associated process and practices.


The TCDSB and Gallagher value inclusivity and diversity in the workplace and encourage applicants from diverse backgrounds and equity seeking groups.

TCDSB and Gallagher are both committed to accommodating applicants with disabilities throughout the hiring process, in accordance with the Accessibility for Ontarians with Disabilities Act (AODA). If you require accommodation during any stage of the recruitment process, please let us know. This document is available in alternate format(s) upon request.

If you are interested in being considered for this opportunity, please forward your resume and a cover letter to:

Gallagher Executive Search & Leadership Advisors

Sup Das
Practice Lead - Technology, Principal

Karen Hsiung
Senior Client Partner