Career Transition:

If your employer has provided you with Career Transition Support through Gallagher, click here to get started.

Get Support With:
  • Career planning + assessment
  • Resume development + optimization
  • Creating your professional online profile
  • Networking training + events
  • Interview preparation

Current Opportunities

Director of Technology for Learning | Calgary Academy

The Organization

Calgary Academy was founded in 1981 and is a private school renowned for empowering unique learners to unleash their potential while pursuing lives of passion and purpose. Since its earliest days as pioneers in inclusive education, Calgary Academy has lived and breathed by a simple yet profound ethos: place the individual needs of each student at the heart of everything they do. Rooted in this commitment, the spirit of Calgary Academy is embodied by a unique and authentic energy. The organization’s growth-oriented, nurturing and inclusive culture promises that each student will be empowered to exceed their own expectations and to believe in the boundless opportunities the future holds. Hope, belonging, and a palpable sense of optimism fill the school and hearts of all employees.

Calgary Academy’s four pillars and guiding principles are woven throughout innovative programming proven to be incredibly successful since its inception; however, the true essence of Calgary Academy can only be captured by a feeling that is difficult to portray with words but undeniable in spirit. It is a feeling that fosters safety and life-long loyalty, and it is why Calgary Academy is a place so many families, students, staff, and alumni are so proud to call home.

Calgary Academy is one of three entities within The Headwater Learning Group which this role will support. Through the partnership with related organizations, Headwater Learning Foundation and Headwater Learning Solutions, the organizations are broadening their collective impact to foster and support the advancement of education.

Vision: To be a beacon of possibility for richly personalized, engaging learning experiences that empower learners to pursue lives of passion and purpose.

Mission: We design engaging, dynamic, student-centered experiences that nurture a caring, inclusive culture and instill a love of learning.

For further information about Calgary Academy, please visit:

For further information about Headwater Learning Solutions, please visit:



The Opportunity

Reports to:Executive Director of School Operations – Calgary Academy
Direct Reports:3
Location:Calgary, AB



The primary purpose of the Director of Technology for Learning is a visionary leader who guides Calgary Academy technology-related teaching and learning practices as well as addressing the technology infrastructure and corporate business needs of Headwater Learning Group. As a member of the School Leadership Team, (SLT) the Director will work in tandem with the Executive Leadership Team (ELT) and SLT to meet all business and strategic goals.

The Director of Technology for Learning directly leads the Information Technology team and partners closely with various functions to support ideal outcomes. The Director creates a modern technology-rich environment, which empowers both students and staff. The Director leads and executes the vision of the Information Technology Department as a service team within the organization that enables others to make a positive impact for all members of our community.

The Director of Technology for Learning reports to the Executive Director of School Operations and adheres to the duties and responsibilities identified in the job description, employee policies and procedures, and Support Staff Terms of Employment.

The Director of Technology for Learning will exemplify the REACH principles that guide behaviour across the Calgary Academy Society and Headwater Learning Foundation and Headwater Learning Foundation Solutions. The REACH principles are Respect, Enthusiasm, Altruism, Commitment, and Honesty. All employees endeavor to serve and support the achievement of Headwater Learning Group’s Strategic Plans.


Key Accountabilities


Develops and implements strategic vision for the use of technology in the organization in both the academic, administrative, and corporate systems.

Utilizes research to shape the effective use of technology in the school and corporate areas.

Supports the creation and implementation of innovative, and technology-infused learning environments.

Develops a sustainable technology environment through the distribution of knowledge, documentation, and fiscal responsibilities.

Provides critical information to support decision-making regarding academic and administrative technology matters.

Develops and maintains partnerships beneficial to the organization related to technology.

Champions changes in curriculum design and delivery related to technology in conjunction with other leaders in the department and in schools.

Ensures all educators have access to the appropriate tools to support learning and administrative functions.

Ensures technology resources are used safely and responsibly while minimizing restrictions on access.

Challenges practices to evolve and maximize technology efforts.

Recommends Information Technology and Technology for Learning policies and procedures by evaluating organization outcomes.

Prepares proposals for major, complex and long-term technical solutions, including cost analysis, time required, and alternative approaches.

Directs operations in executing production tasks according to a documented schedule that meets or exceeds stakeholder expectations.

Represents the IT function at SLT, ELT, and Board meetings when appropriate.

Guides education and professional learning, and professional practice for IT staff.

Maintains knowledge and capacities on the forefront of IT education, providing recommendations to SLT for future opportunities that serve better student learning outcomes.

Responsible for planning and implementing best risk-management practices for all IT systems.  This includes having effective IT security and backup strategies along with business continuity and critical incident recovery readiness.

Demonstrate commitment and adherence to Professional Practice framework(s) ensuring support of performance and growth areas of direct reports through meaningful conversation, relevant and timely feedback and collaboration on the completion of annual portfolios and professional growth plans; all of which aligns with the individual’s respective Quality Standard.


Effectiveness and Efficiency:

Designs and provides professional learning opportunities for staff to infuse technology into various environments.

Documents processes including building guides and tools to help others utilize and support technology.

Actively establishes plans to build capacity of team, to share knowledge and reduce risk.

Oversees and provides network level support for business applications.

Oversees software installation and equipment troubleshooting across departments.

Analyzes complex organizational needs presented by the user community and/or clients and recommends technical solutions.

Ensures the consistency and maintenance of existing applications by creating, maintaining, and enforcing standards and procedures.

Performs liaison duties between users, operations, and programming personnel in the areas of systems design, modifications or trouble shooting.

Establishes and measures IT performance relative to cost, value creation and stakeholder satisfaction to ensure data driven decision-making is consistently followed.

Protects the organization and its operations against IT risks, including unauthorized access to information, data integrity problems, loss of system capability, and poor service levels.



Demonstrate innovation through fostering creativity, adopting new practices and technologies, modernization, research, and partnerships.

Create an environment that fosters creativity, agility and innovative ideas and remove barriers that stifle the innovation spirit.


Candidate Profile

The successful candidate will have the following:



Bachelor’s degree in relevant technology areas and/or a valid Alberta Teaching Certificate.; Teaching experience is preferred, but not required.

Master’s degree in Education Technology is considered an asset.

Certification that are considered an asset are:

  • Project Management (PMP, ITIL, CSM)
  • Microsoft (Azure, 365, Server, Security, Power Platform)
  • Networking (Cisco, Extreme, Fortinet)
  • Cybersecurity (CEH, CISM, CISSP)



7-10 years of proven track record in leading high-performance teams and technology leadership experience, including

  • Network design, security, and support, Cisco/Extreme networking equipment, VoIP systems,
  • Enterprise hybrid computing environment including Microsoft technologies and Apple ecosystem
  • Azure, VMWare, and other cloud platforms
  • Fortinet firewall
  • PowerShell, KQL, SQL, and other scripting languages
  • Understanding of PCI Compliance standards and requirements
  • Knowledge of PowerSchool LMS and PASI compliance standards

Skilled forward-facing leader with high levels of professionalism.

Proven record of accomplishments in planning, designing, implementing and supporting a wide variety of technologies including infrastructure, client devices, cloud-based services, and system applications.

Broad knowledge of industry standards and best practices in the use of technology in schools.

Demonstrated strengths in communication, problem resolution, and building effective relationships.

Demonstrated skills in translating highly technical aspects of various technologies into terms non-technical people can understand.


Competencies and Attributes

Fostering Effective Relationships- A leader builds positive working relationships with members of the school community and local community.

Modeling Commitment to Professional Learning– A leader engages in career-long professional learning and ongoing critical reflection to identify opportunities for learning and improving leadership.

Embodying Visionary Leadership– A leader collaborates within the organization to create and implement a shared vision for employee success, engagement, learning and well-being.

Leading a Community of Learners– A leader nurtures and sustains a culture that supports evidence-informed practice and learning.

Supporting the Application of Foundational Knowledge about First Nations, Métis and Inuit – A leader supports the organization in acquiring and applying foundational knowledge about First Nations, Métis and Inuit.

Develop Leadership Capacity– A leader provides opportunities for members of the organization to develop leadership capacity and to support others in fulfilling their roles.

Managing Operations and Resources – A leader effectively directs operations and manages resources.

Understanding and Responding to the Larger Societal Context – A leader understands and appropriately responds to the political, social, economic, legal and cultural contexts impacting the organization.

Passion for how technology can improve and enhance education.

Passion and expertise in Microsoft SharePoint as an enterprise platform.

Passion for supporting technology to improve work and learning environments.

Confidence and ability to work with technology vendors to deliver highly effective solutions.

Positive outcome of a current Criminal Record and Vulnerable Sector Check.

Equal Opportunity

Calgary Academy is committed to equity, diversity and inclusion and recognizes that a diverse team benefits and is essential to service excellence. Calgary Academy welcomes applications from all qualified individuals and encourage women, members of racialized communities, indigenous persons, persons with disabilities, and persons of any sexual orientation or gender identity to confidentially self-identify at time of application.  In accordance with the provincial legislation, accommodation will be provided by Gallagher and Calgary Academy throughout the recruitment, selection and/or assessment process, upon request, to applicants with disabilities. All qualified candidates are encouraged to apply.


How to Apply:

Please send your resume in Word or PDF format to: Copy and Paste the following job title and code and place it in the subject line of your email so we can identify the job and confirm receipt of your application:
Director of Technology for Learning Director of Technology for Learning | Calgary Academy - AB - Calgary and Area (OTIAPPLY)

Please note that only those candidates meeting the selection criteria, established by our client, will be contacted further. Although we may not contact you directly for this particular role, all applications will be reviewed as we would like to consider you for future opportunities that may be appropriate. We encourage you to continue to visit our website at as our opportunities are updated on a regular basis.