Chief Information Officer (Confidential)

THE ORGANIZATION

Our client is a nationally recognized transportation organization with operations across Canada. Since its inception, the company has experienced meaningful evolution—broadening its network, strengthening operational capabilities, and advancing its technology and customer experience to meet the expectations of a fast-moving marketplace.

Guided by a performance-driven operating model focused on productivity, value creation, and service reliability, the organization has steadily extended its reach across North America and internationally.

Through continued investment in scalable digital platforms, enterprise systems, and customer-facing technologies, the company is reinforcing the foundation required for sustained, long-term growth.

With a strong people-first culture and a commitment to continuous improvement, the organization is now prioritizing the advancement of its technology, digital, and information ecosystems to support its next phase of expansion.

This is a confidential search. Further details about the organization will be shared with candidates who are shortlisted for the opportunity.

THE OPPORTUNITY

The CIO will begin with a comprehensive assessment of the organization’s current information systems and technology landscape – across both internal enterprise platforms and externally facing customer solutions. The leader will evaluate the full technology stack, including infrastructure, enterprise systems, digital channels, data architecture, and e-commerce capabilities, to determine effectiveness, scalability, integration, and alignment with business priorities.

Following this review, the role will develop and execute a cohesive enterprise-wide information systems strategy grounded in a “one infrastructure” vision. This includes determining which technologies should be optimized and retained, where consolidation is required, and which new systems must be introduced to create a unified, scalable environment that supports Finance, HR, Operations, data and analytics, and the overall customer experience.

A key component of the mandate is assessing and mitigating risk – including cybersecurity, data governance, compliance, privacy and business continuity – while elevating both the digital customer journey and the internal employee experience to the same high standard.

The CIO will align technology investments with strategic and operational priorities, delivering a clear, enterprise-wide roadmap that defines key initiatives, sequencing, timelines, and capital requirements – balancing stakeholder needs to enable sustainable growth and long-term scalability.

RESPONSIBILITIES & ACCOUNTABILITIES

Vision, Strategy & Transformation

• Define and lead the long-term enterprise technology and digital vision aligned to corporate growth, operational performance, and customer experience objectives.
• Establish and execute a “one enterprise system” strategy that unifies platforms, data, and digital capabilities across the organization.
• Develop a multi-year enterprise technology roadmap outlining priorities, sequencing, investment requirements, and measurable outcomes.
• Serve as a cross-functional transformation leader, driving technology adoption, organizational alignment, and enterprise-wide change.

Technology Infrastructure Review, Rationalization & Modernization

• Conduct a comprehensive assessment of the current technology stack, infrastructure, enterprise systems, and integrations across all business units.
• Rationalize and consolidate systems to eliminate redundancy and fragmentation, strengthening scalability and operational efficiency.
• Lead modernization initiatives including cloud transformation, platform upgrades, and architecture redesign to support long-term growth.
• Oversee mission-critical system transitions with disciplined change management and contingency planning to prevent operational disruption or system outages.

IT Governance, Data Privacy & Cybersecurity Risk Management

• Establish formal IT governance frameworks, policies, and controls – including data management, privacy protection, and access protocols where gaps exist.
• Design and implement modern cybersecurity practices to safeguard customer and company data.
• Identify and mitigate enterprise technology risks, ensuring business continuity and resilience.
• Strengthen compliance, audit readiness, and vendor risk management across all systems.

Digital Transformation, E-Commerce & Customer Experience

• Advance digital platforms and e-commerce capabilities to deliver a seamless, end-to-end customer journey.
• Partner with Commercial and Operations teams to ensure digital solutions directly support revenue growth and performance objectives.
• Ensure a constantly evolving, relevant, attractive and future-facing digital performance marketing offering.
• Ensure external digital experiences are fully integrated with back-end enterprise systems.

Data, Analytics & Business Intelligence

• Develop a comprehensive business intelligence capability, including a comprehensive data warehouse and business reporting and analysis tools.
• Embed data governance and analytics frameworks to strengthen real-time decision-making.
• Deliver actionable insights across Finance, HR, Operations, and Commercial functions.
• Leverage data platforms to expand enterprise value and performance visibility.

Employee Technology Experience & Service Excellence

• Elevate the internal employee digital experience through modern collaboration tools, intranet/app platforms, and workplace technologies.
• Build a responsive service desk and end-user support model that enhances productivity.
• Align internal technology experience standards with the organization’s external customer experience ambitions.
• Maintain disciplined IT asset management and lifecycle oversight.

Leadership, Culture & Strategic Partnerships

• Build and lead a high-performing, future-ready technology and digital team.
• Act as a trusted advisor to the executive team and Board on technology strategy and risk.
• Manage strategic vendor and development partnerships to ensure quality, reliability, and alignment to enterprise objectives.
• Foster a culture of accountability, innovation, and continuous improvement.

MEASURES OF SUCCESS

• Develop and launch an enterprise-wide IT strategy grounded in a comprehensive assessment of current systems, culminating in a “one technology” roadmap aligned to long-term business vision, scalability, and operational needs.
• Identify and mitigate enterprise technology risks, conducting a full cybersecurity and vulnerability assessment and implementing a structured plan to close gaps, strengthen monitoring, and enhance resilience.
• Establish formal IT governance and compliance frameworks, including data governance, privacy policies, access controls, and regulatory alignment to ensure enterprise-wide accountability and risk oversight.
• Lead a scheduled customer-facing software transformation – executing it with rigorous change management and contingency planning to ensure zero unplanned downtime and uninterrupted customer transactions throughout the transition.

THE INDIVIDUAL

We are seeking a strategic and business-minded technology leader who brings deep technical expertise across infrastructure, digital platforms, e-commerce, data, cybersecurity, and enterprise systems. The ideal candidate has successfully led complex technology environments, including systems integration and customer-facing platform modernization, and is able to translate technical strategy into clear business outcomes.

Equally important, this individual is a collaborative, people-first leader who builds trust across functions, rolls up their sleeves, and guides teams confidently through transformation. Thriving in fast-paced environments, they balance long-term vision with operational discipline, fostering accountability, resilience, and continuous improvement while positioning technology as a true enabler of sustainable growth.

Education

• Bachelor’s degree in Computer Science, Information Technology, or a related field is required.
• An advanced degree (e.g., Master’s) is considered a strong asset but not required.

Experience

• 15+ years of progressive IT leadership experience, including senior-level responsibility for enterprise systems, digital platforms, infrastructure, and technology strategy.
• Experience within transportation, logistics, travel, tourism, hospitality, or other operationally intensive, customer-centric industries is considered a strong asset.
• Demonstrated success leading and motivating high-performing teams, with the ability to inspire engagement, accountability, and strong execution across diverse and remote environments.
• Strong financial and business acumen, including experience with budgeting, business case development, technology investment planning, and project management to support strategic implementation.
• Proven ability to make data-informed decisions, leveraging analytics, stakeholder input, and operational insights to guide enterprise technology priorities.
• International exposure and experience leading vendors and remote development teams, with an understanding of global operational considerations.
• Commitment to staying current with emerging technologies and industry trends, with the ability to conduct technology assessments and translate innovation into practical business value.

Competencies and Knowledge

• Enterprise Technology Strategy & Execution – Demonstrates the ability to assess complex technology environments, define a clear “one technology” vision, and execute a multi-year roadmap that aligns infrastructure, digital platforms, and data capabilities to business growth objectives.
• Cybersecurity, Risk & Governance Leadership – Brings strong expertise in identifying technology and data risks, establishing governance frameworks, strengthening cybersecurity posture, and ensuring compliance with privacy and regulatory requirements.
• Digital Transformation & Platform Modernization – Proven experience leading large-scale, customer-facing software transformations with disciplined change management, ensuring seamless integration, system reliability, and minimal operational disruption.
• Cross-Functional Collaboration & Influence – Effectively partners with Commercial, Operations, Finance, and HR leaders, breaking down silos and aligning stakeholders around shared priorities and enterprise-wide outcomes.
• People Leadership & Organizational Change – Builds high-performing teams, fosters psychological safety and accountability, and leads organizations confidently through technology-driven change with resilience, clarity, and steady leadership.

Personal Profile

• People first, empathetic leader: Brings warmth, authenticity, and high emotional intelligence, building trust quickly while supporting teams through heavy workloads, burnout risk, and ongoing transformation.
• Entrepreneurial and improvement-driven: Brings energy, initiative, and the mindset to build, fix, and evolve systems; doesn’t sit back but actively drives continuous improvement and encourages the same in others.
• Hands-on and curious leader: Naturally rolls up their sleeves, digs into systems and processes, asks thoughtful questions, and actively seeks to understand how technology, data, and operations fit together.
• Calm, resilient, and steady under pressure: Shows perseverance in navigating complexity, legacy systems, shifting priorities, and organizational change.
• Practical problem solver: Applies strong judgment and common-sense decision-making to evaluate fragmented systems, prioritize work, and implement solutions that are realistic, scalable, and aligned to business needs.
• Collaborative culture builder: Breaks down silos, fosters alignment across teams, and promotes an environment rooted in openness, accountability, and shared goals, helping rebuild and strengthen internal culture.
• Clear communicator: Communicates with transparency, navigates cross-functional relationships with ease, and aligns stakeholders from all aspects of the business including external partners.
• Team developer and coach: Invests in people, provides coaching and clarity, raises performance expectations, and creates conditions for individuals and teams to grow, collaborate, and deliver at a higher level.

COMPENSATION

A competitive compensation package awaits the successful candidate.

LOCATION

This position is open to applicants across Canada. Preference may be given to candidates residing in a city where the organization maintains a corporate office presence. Relocation will be supported if required. Final location and flexibility will be discussed as part of the hiring process.

TRAVEL

Depending on the successful candidate’s primary location, regular travel to other corporate office locations will be required.

WORK ENVIRONMENT

The CIO will be based in one of the organization’s corporate offices, with frequent travel to other office locations as required. The role may also involve a variable work schedule, including occasional evenings, weekends, and holidays, to support operational needs.

HOW TO APPLY

For the opportunity to join our client in the role of Chief Information Officer (CIO), please email your resume to DreamBig@profoundtalent.com referencing Position ID #APXH-476383.

Should you have any inquiry regarding this position, please contact Paul Phillips at 587-200-0114 ext. 105 or Terri Davis at ext. 101.

For further information on ProFound Talent Inc. please visit: www.profoundtalent.com

EQUAL OPPORTUNITY 

ProFound Talent is a woman owned and operated business, recognized and certified by Women Business Enterprise (WBE). We pride ourselves in supporting equity, diversity, and inclusion initiatives in our recruitment processes and in our work environment, where every individual feels valued and respected. We welcome applications from all qualified individuals to which you may confidentially share your accommodation needs at time of application. We will adjust our processes to ensure you have an inclusive, fair, and respectful experience that allows you to represent yourself in your unique and most authentic way.

* We thank all applicants for your submissions, however only candidates being considered for this role will be contacted. *