Director, Asset Management and Project Delivery

Porter Airlines (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. Central to this transformation effort is the Director of Development and Delivery, a critical role entrusted with bringing these strategic visions to fruition. Tasked with steering vital components of the transformation, including the adoption of advanced technologies and agile practices, their role is fundamental to the initiative's success. By ensuring the seamless execution of projects that align with Porter's visionary objectives, they not only contribute to the organization’s technological evolution but also to its overall strategic success.
The Director, Development and Delivery plays a pivotal role in driving the execution of technology solutions that align with Porter’s strategic business objectives. With a strong focus on execution, this role involves guiding the team through significant change, injecting energy and enthusiasm into every project. The Director, Development and Delivery, will lead initiatives that transform IT processes and enhance customer experiences through innovative technology solutions, prioritizing performance, optimization, and reliability. This encompasses exemplifying leadership through embracing change, cultivating a space where innovation is at the forefront, and championing a culture of ongoing learning and professional development throughout the team.
Success in this role will be measured using Key Performance Indicators such as project delivery success rate, systems uptime, innovation implementation, team engagement and development, operational efficiency improvements, cybersecurity compliance, quality of vendor management and strategic partnerships, and client satisfaction.

Strategic Leadership and Planning: Spearhead the strategic planning and execution of system implementations and maintenance, aligning closely with Porter's business objectives and the rapid adoption of technological advancements. Embrace Change and Foster Resilience: Champion adaptability and resilience within the IT department, ensuring the team remains agile and responsive to the dynamic nature of the technology landscape.
Leadership in Project Delivery Methodologies: Champion the rollout, adoption and refinement of leading project delivery methodologies, including Lean, Agile, and Design Thinking, across all technology initiatives to shift project efficiency, delivery quality, and stakeholder satisfaction.
Work collaboratively with other teams to embed these methodologies into the fabric of the project lifecycle, ensuring a flexible, responsive, and user-centered approach to technology development and implementation.
Continuously refine these processes to enhance efficiency, foster innovation, and ensure that projects exceed business and user expectations.
Balanced Approach to Development: Oversee a balanced integration of custom software development and Commercial Off-The-Shelf (COTS) solutions. Foster robust collaboration with cross-functional IT leaders, including those in Architecture, Solution Delivery, Infrastructure, Cybersecurity, Data, and Innovation teams. Innovation and Architecture Alignment: Work closely with the IT Architecture leader to ensure the design and delivery of solutions align with Porter’s target architecture models. Cultivate a strong partnership with the Cybersecurity team to seamlessly integrate security measures into all technology initiatives, ensuring Porter’s digital assets are safeguarded against evolving threats.
Data-Driven Decision Making: Partner with the Data team to harness analytics and insights, thereby sharpening decision-making processes, refining customer experiences, and optimizing operational efficiency.
Champion a platform mindset focused on performance, optimization, and reliability. Continually assess and enhance the technological ecosystem to meet business demands while upholding high standards of performance and reliability. Engineering Excellence: Develop and oversee Engineering practices, establish coding standards, and implement CI/CD pipelines. Utilize advanced tools like QA automation, Robotic and Cognitive Process Automation, Generative AI to boost efficiency and spearhead delivery innovation.
Change Management and Transformation Support: Provide pivotal transformation support as the team navigates new ways of working. This entails effective change management and ensuring the team is well-equipped with the necessary skills and tools for a seamless transition.
Team Management and Development: Manage and mentor a diverse team, fostering an inclusive culture that reflects Porter’s organizational values and goals. 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.
Bachelor’s degree in computer science, engineering, or related field. At least 20 years of diverse experience across various IT roles in different organizations, with a minimum of 10 years in leadership and management positions, demonstrating a comprehensive understanding of supporting a wide array of business clients and leading high-performing agile teams.
Proven expertise in implementing project management methodologies across projects, including Lean, Agile, and Design Thinking. Demonstrated ability to integrate these methodologies into project lifecycles, enhancing efficiency and focusing on user-centric solutions.
Extensive experience leading technology strategy, covering both custom software development and the integration of Commercial Off-The-Shelf (COTS) solutions, especially for corporate functions (Finance, HR, etc.), Digital and Marketing, and Operations teams.
Expertise in adopting a platform mindset, prioritizing performance, optimization, and reliability across technology solutions.
Knowledgeable in cybersecurity fundamentals, with experience in collaborating with cybersecurity teams to seamlessly integrate security practices into technology projects and initiatives.
Extensive experience leveraging and managing third-party vendors and partners to enhance in-house capabilities:
Employed multi-shoring models effectively, providing thought leadership and building capacity to meet strategic and operational demands.
Skilled in negotiating and maintaining productive relationships with vendors, ensuring the delivery of high-quality services and solutions in line with Porter’s goals.
Robust experience in facilitating collaboration across diverse IT disciplines (Program Management, Architecture, Infrastructure, Cybersecurity, Data, and Innovation). Ability to leverage these partnerships to augment technology capabilities and provide comprehensive support across all business areas.
Proficiency in leading change management efforts, preparing teams for successful adaptation to new methodologies and technologies.
Proven track record in managing and mentoring diverse teams, fostering an inclusive culture aligned with the organization's values. Capable of influencing, building consensus, and fostering strong executive and cross-functional collaborations.
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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