Executive Advisor, Technology

WestJet Group•Calgary, AB

19h•Onsite

About The Position

The Executive Office at WestJet functions as an internal advisory organization focused on creating sustained, long-term value. It acts as a strategic partner to the Executive Committee (ExComm), serving as a multidisciplinary team that drives strategic initiatives across the organization. Roles within the Executive Office are designed for high-potential talent and serve as a development platform for future leadership. The Executive Advisor, Technology is a key member of this team, responsible for advancing strategic priorities within WestJet's technology organization. Reporting to the Director, Corporate Strategy and collaborating closely with the Chief Information Officer (CIO), this role integrates, provides thought partnership, and offers strategic advice to the Technology Senior Leadership Team.

Requirements

Minimum of 7–10 years of progressive experience in technology, digital transformation, enterprise strategy, corporate strategy, or executive advisory roles within large, complex, or matrixed organizations.
At least 5 years of direct experience partnering with senior technology executives, ideally a CIO or equivalent, providing strategic guidance and supporting enterprise-level decision-making.
Demonstrated success in internal consulting, strategy, transformation, portfolio management, or Chief of Staff–style roles, ideally within airline, travel, retail, technology, or similarly complex, digitally enabled industries.
Proven ability to lead and support cross-functional initiatives across technology strategy, enterprise architecture, delivery performance, cybersecurity, data, vendor management, investment prioritization, and productivity, driving alignment and execution across diverse stakeholder groups.
Strong familiarity with corporate governance processes, including preparation of Board and executive committee materials, leadership meeting coordination, performance planning cycles, and enterprise portfolio governance.
Exceptional analytical and communication skills, with a track record of distilling complex qualitative and quantitative inputs into high-impact insights and executive-level presentations.
Experience navigating organizations through strategic change, technology modernization, cultural transformation, or high-growth phases, with a focus on enterprise integration, operational continuity, and disciplined execution.
Bachelor’s degree in Business, Engineering, Computer Science, Information Systems, or a related field required.

Nice To Haves

MBA, technology-focused graduate education, or equivalent experience strongly preferred.

Responsibilities

Operate across strategic, operational, and tactical levels, providing oversight for critical and confidential technology initiatives that span functions or fall outside traditional reporting structures.
Act as a trusted advisor and strategic thought partner to the CIO and Technology Senior Leadership Team, serving as a sounding board, offering fresh perspectives, and triaging executive-level inputs.
Facilitate the flow of critical information across internal and external stakeholders, serving as an extension of the CIO and a key liaison across the Group’s technology, digital, data, cybersecurity, and operational ecosystem.
Navigate complex cross-functional discussions with professionalism and neutrality, managing competing perspectives across technology, commercial, operations, finance, people, and corporate functions without departmental bias.
Lead internal planning and governance for Technology teams, including Business Reviews, OKRs (objectives and key results), Budget alignment, portfolio prioritization, leadership offsites, Board materials, ExComm updates, and town halls.
Provide analytical and organizational support on key technology initiatives, acting as the primary conduit between the Executive Office and technology-related departments.
Maintain a comprehensive understanding of major Technology functions, including enterprise architecture, technology delivery, digital product, cybersecurity, infrastructure, data, and AI; collaborate closely with their leaders.
Break down silos and drive enterprise alignment by integrating cross-functional efforts and ensuring connectivity across strategic initiatives, transformation programs, and technology-enabled business outcomes.
Integrate, connect, and ensure a holistic approach for workstreams that could otherwise remain siloed; work in close collaboration with other members of the Executive Office to ensure alignment across critical priorities, cross-functional strategic initiatives, and special projects.
Support the Technology organization through periods of complexity, ambiguity, and transformational change, reinforcing alignment with WestJet’s corporate strategy, enterprise roadmap, risk posture, and investment priorities.
Review and facilitate strategic business planning to ensure cohesive alignment between departmental, product, portfolio, and corporate objectives; ensure key strategic programs are appropriately prioritized within the organization.
Facilitate and review strategic business discussions to ensure objectives align and tie across the overall technology strategy and the WestJet Group’s corporate strategy; partner closely with delivery and governance teams to ensure alignment and continuity of information.
Prepare high-impact presentations for ExComm and the Board of Directors, distilling complex technology, financial, risk, delivery, and operational inputs into actionable insights that enable swift, informed decision-making.
Empower teams by representing the CIO where appropriate, reinforcing clarity of ownership, decision discipline, accountability, and proactive execution.