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CEO / Managing Director

3 months ago

Toronto, Ontario, Canada Porter Airlines Inc. Full time
Porter is embarking on a significant technology transformation journey to reshape its IT landscape over the next 2-3 years.

This ambitious transformation is centered around several pivotal pillars including modernizing applications, streamlining project delivery, and igniting innovation throughout the organization.

The Managing Director, IT Systems and Delivery, will act as a linchpin in this endeavor, serving as the chief champion and transformation lead.

While directly accountable for a subset of transformation pillars, their overarching responsibility is to orchestrate the comprehensive progress of IT's transformation, aligning closely with Porter's strategic ambitions.

Reporting to the Senior Vice-President (SVP) and the Chief Information Officer (CIO), the Managing Director, IT Systems and Delivery, will play a pivotal role at Porter.

They are set to lead the company's ambitious IT transformation journey.

As one of the primary champions of this initiative, the Managing Director, IT Systems and Delivery, will oversee key parts of the transformation.

They are directly responsible for initiatives such as the Enterprise Data Program, the launch of an innovation practice, and the establishment of a QA Automation Center of Excellence.

Their duties also include driving a cultural shift within the IT department. They will embody and advocate for change, agility, innovation, and a data-driven approach.

The broad responsibilities of the Managing Director, IT Systems and Delivery, also involve ensuring the successful execution of strategic transformation pillars.

They will inspire and prepare the IT team for future technological landscapes. This leadership position demands more than traditional management skills. It calls for a dynamic approach to reshape the IT team's culture. The Managing Director, IT Systems and Delivery, will lead by example, welcoming change and fostering an innovative environment.

The success of the Managing Director, IT Systems and Delivery, hinges on their leadership effectiveness in driving Porter's IT transformation.

Key performance indicators include advancing the Enterprise Data Program, project delivery success rate and establishing an innovation practice and a QA Automation Center of Excellence.

Additional measures include operational efficiency improvements, effective use of third-party vendors, stronger client relationships, and notable advances in cultural change and talent development within the IT department.



Lead IT Transformation Initiatives:
Spearhead Porter's IT transformation, aligning with strategic pillars to modernize the IT landscape and meet business objectives.

Guide the IT department's transformation with a keen focus on resilience and adaptability, setting a standard for leadership that thrives on change and uncertainty.


Maintain a Transformation Scorecard:
Develop and oversee a comprehensive scorecard to track and report on the progress of Porter's IT transformation.

Optimize Project Delivery Methodologies:

Collaborate with the Director, Development and Delivery to embed Lean, Agile and Design Thinking principles, enhancing project efficiency, delivery quality, and stakeholder satisfaction.

Promote collaboration across IT disciplines and Solutions Delivery functions— Program Management, Architecture, Infrastructure, Cybersecurity, Data, Development and Delivery, and Innovation teams—to ensure cohesive and integrated efforts toward achieving transformation goals.

Assume a pivotal role in integrating selected third-party vendors into Porter's IT strategy, positioning these collaborations as catalysts for transformation beyond conventional support functions to achieve transformative goals and operational efficiencies.

Advance the

Enterprise Data Program:

Drive the expansion of the Enterprise Data Program, using data analytics and AI to enable actionable insights and a data-driven culture.


Champion Agile Transformation:
Advocate for and support the integration of Agile methodologies, promoting a culture of flexibility, continuous learning, and adaptation.

Cultivate a Learning Culture and Communities of Practice: Encourage continuous learning and the development of communities of practice, fostering an environment where knowledge sharing, and collaboration thrive.



Attract Next Generation Talent Through Academic Partnerships:

Establish partnerships with universities and academic institutions, creating pathways for young talent to join and enrich the IT department.


Reinforce Inclusion in Transformation:

Anchor our commitment to equity, diversity, and inclusion within the heart of Porter's IT transformation journey by actively weaving diverse perspectives into our strategy and execution.

Ensure Quality and Compliance in Delivery: Oversee the implementation of QA automation and standards to ensure high-quality project delivery that meets specifications and compliance requirements.

Create a QA Automation Center of Excellence: Develop a center focused on advancing QA practices and technologies, boosting operational efficiency and product reliability.


Cultural Evolution:
The expectation for this leadership role extends beyond traditional management, requiring a dynamic approach to actively shape and evolve the IT department's culture

Results Focus:
Focusing efforts on achieving high quality results consistent with the organization's standards.
Listening and communicating openly, honestly, and respectfully with different audiences, promoting dialogue and building consensus.

Treating others fairly, honestly, and respectfully, furthering the integrity of the organization and its relationships of trust with team members and the broader community.


People Leadership:
Assuming a leadership role in helping others achieve excellent results.

Bachelors degree in computer science, Engineering, Business Administration, or a closely related discipline, providing a foundational understanding of both technology and business principles.

Over 20 years of extensive and progressive experience in IT and product development across varied organizations including a significant tenure of at least 10 years in leadership roles, underscored by a notable ability to lead cross-functional teams and effectively navigate complex organizational structures.

Demonstrated success in evaluating, testing, and implementing innovative technologies, as well as spearheading major innovation and transformation initiatives within large, complex environments.

Expertise in enhancing enterprise data programs, utilizing data analytics and artificial intelligence to bolster strategic decision-making and advance business objectives.

Solid experience in initiating innovation practices and advocating for Agile methodologies, focusing on the rapid development, and scaling of new technologies.

Strong commitment to equity, diversity, and inclusion, with experience in deploying EDI strategies and leading cultural change initiatives within the workplace.

Exceptional ability to foster collaboration across multidisciplinary teams and build robust partnerships with external vendors to enhance project outcomes and technological capabilities.

Demonstrated skill in engaging with academic institutions to attract young talent, marketing IT as a dynamic field ripe for innovation and growth.

A passion for creating a learning culture and communities of practice, promoting continuous improvement, knowledge sharing, and skill enhancement.

Your unique skills, perspectives, and background might be precisely what's needed to drive our transformation forward.

Toronto Downtown Office (250 Yonge Street) #LI-Hybrid

Since 2006, Porter Airlines has been elevating the experience of economy air travel for every passenger, providing genuine hospitality with style, care and charm.

Porter's fleet of Embraer E195-E2 and De Havilland Dash 8-400 aircraft serves a North American network from Eastern Canada. Visit or follow @porterairlines on Instagram, Facebook and Twitter.
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