This position requires in-person collaboration up to five days a week. This arrangement is subject to change based on business requirements.
Overview of role: The Executive Office sits at the core of the WestJet Group and functions as an internal advisory organization that enables sustained, long-term value creation. Positioned as a trusted partner to the Executive Committee (ExComm), this high-performing, multidisciplinary team acts as a strategic force multiplier across the organization. Roles within the Executive Office are designated for top-tier, high-potential talent and serve as a developmental platform for future leadership roles.
As a member of this team, the
Executive Advisor, Technology plays a pivotal role in advancing strategic priorities across the WestJet Group's technology organization. Reporting to the Director, Corporate Strategy and working in close partnership with the Chief Information Officer (CIO), this role serves as a key integrator, thought partner, and strategic advisor to the Technology Senior Leadership Team.
Key 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
Competencies & Attributes- Strategic and analytical mindset with the ability to synthesize qualitative, quantitative, financial, technical, and risk inputs into concise, compelling insights
- Strong business and technology acumen; able to connect enterprise strategy, customer and guest experience, operational resilience, digital modernization, data, AI, cybersecurity, and financial outcomes
- Politically astute and organizationally savvy; skilled at anticipating risks, surfacing trade-offs, and mitigating challenges before they materialize
- Demonstrated excellence in project, portfolio, and stakeholder management, with meticulous attention to detail and a bias for execution under tight timelines
- Highly trusted and discreet; adept at handling sensitive information, technology risk matters, investment decisions, and executive communications with integrity and professionalism
- Exceptional communication and executive writing skills; able to tailor messaging to a variety of audiences and amplify leadership narratives across different mediums
- Collaborative and team-oriented, yet self-directed and confident in assuming leadership without formal authority
- Optimistic, resilient, and solution-focused, with a passion for delivering meaningful organizational impact through technology-enabled change
Professional Experience & Qualifications- 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; MBA, technology-focused graduate education, or equivalent experience strongly preferred
The benefits of being a WestJetter:WestJet provides all WestJetters with a competitive total rewards package. On top of that, we offer:
- A fun and friendly culture with colleagues who work together to win
- Travel privileges for you and your family, effective from your start date
- Savings and Benefit programs that are flexible to meet your specific needs
Think we're a great fit? Apply now!
