Head of Technology & Innovation
Reporting To : CEO
Location: Toronto, Canada
Term : Full-Time
Overview
Butterfield & Robinson is embracing a new era of innovation—where technology and travel meet to create unforgettable experiences. This newly created role will lead our Technology team and play a central part in shaping how digital tools and AI power the next chapter of B&R. We’re looking for a Head of Technology to guide an experienced team, spearhead our digital transformation, drive innovation, and help shape the future of luxury active travel.
A Workplace That Inspires
At Butterfield & Robinson, we believe that extraordinary journeys begin with a talented and inspired team. Our dynamic and supportive work environment fosters creativity, collaboration, and well-being, empowering our employees to push boundaries and create unparalleled travel experiences.
The team at Butterfield & Robinson are part of a vibrant, forward-thinking workplace. We also hold ourselves accountable to the highest standards of responsible, sustainable, and ethical tourism. Transparency and integrity guide our business practices, and we are committed to making a positive impact on both the destinations we explore and the communities we serve. This opportunity is the chance to be part of a community that is passionate about shaping the future of travel.
Responsibilities
Shape B&R’s Technology Vision and Roadmap
Set the long-term strategic direction for technology, data, and digital innovation across B&R — ensuring alignment with strategic goals including business growth, enhanced customer experience, and brand differentiation.
Develop and Execute the Enterprise AI Strategy
Define and oversee an AI roadmap that enhances personalization, operational efficiency, and the traveller experience across digital touchpoints and internal processes.
Foster Cross-Functional Collaboration
Partner with business leaders across the organization to ensure technology investments and data strategies directly enable commercial and customer outcomes.
Own Technology Architecture and Governance
Own the overarching frameworks for technology prioritization, data integrity, and cybersecurity governance — ensuring consistency, scalability, and resilience across all systems.
Guide Resourcing and Vendor Strategy
Optimize internal and external technology capacity to achieve business goals efficiently, ensuring resource allocation aligns with strategic priorities and measurable impact.
Champion Best Practices and Modern Delivery
Drive adoption of pragmatic, modern delivery and software lifecycle practices that enhance speed, quality, and adaptability across our product and data initiatives.
Lead and Inspire a Collaborative Technology Culture
Mentor and empower senior tech leaders and cross-functional teams — creating an environment of trust, innovation, and accountability
Represent Technology at the Leadership Table
Serve as the key strategic voice for technology and B&R’s team of technology experts on the executive team, translating complex concepts into business-relevant insights and influencing decision-making at the highest levels
Bring Industry Perspective and Foresight
Leverage knowledge of the travel, hospitality, and consumer experience sectors to keep B&R ahead of digital trends and emerging opportunities.
Required Skills & Abilities
Qualifications & Skills
Industry Knowledge:
- Background in travel, hospitality, or related consumer-facing industries with complex digital ecosystems and customer engagement models.
Strategic Leadership
- Demonstrated success defining and executing a multi-year technology vision linked to measurable business outcomes.
- Track record of introducing innovation frameworks or prioritization models to guide investment and focus.
AI and Emerging Technology
- Deep understanding of how AI, data science, and automation can transform customer experience and operational efficiency.
- Experience developing or implementing AI-enabled tools or processes.
Collaborative Leadership Style
- Known for empowering specialized leaders (e.g., IT, data, engineering) through clarity of purpose and strategic alignment. Skilled at managing team dynamics with empathy and accountability.
- Deep appreciation for leveraging institutional expertise to accelerate innovation and reduce risk.
Executive Communication and Influence
- Confident engaging with Board, CEO, and senior stakeholders on technology strategy, risk, and ROI.
Technical Breadth
- Familiarity with enterprise architecture, integration, and security principles to ensure alignment and scalability.
Required Experience & Qualifications
Education:
- Bachelor’s degree in Computer Science, Engineering, or related field required.
- Advanced degree (MBA, MSc, or equivalent) preferred.
- Training in IT governance, risk management, and agile delivery.
- Certifications or coursework in change management, executive coaching, or user behavior analytics considered an asset.
Experience:
- 12+ years in progressive technology leadership roles, including at least 5 years at the Director or Head of Technology level (or equivalent).
- Comfortable operating in a lean, hands-on environment — equally able to set strategy with the CEO and roll up your sleeves alongside a small, talented team.
- Proven experience leading technology transformation with real impact (e.g., system modernization, data and platform initiatives, or AI adoption).
- Prior involvement in developing or launching proprietary CRM, digital booking, or personalization platforms.
- Experience setting clear technology priorities and trade-offs alongside the business — deciding what to build, buy or customize, and balancing business objectives and speed of execution against the technology team’s capacity
- A track record of making delivery predictable, so timelines are realistic and stakeholders know what to expect.
Industry Knowledge:
- Background in travel, hospitality, or related consumer-facing industries with complex digital ecosystems and customer engagement models.
Strategic Leadership
- Demonstrated success defining and executing a multi-year technology vision linked to measurable business outcomes.
AI and Emerging Technology
- Deep understanding of how AI, data, and automation can transform customer experience and operations — plus hands-on experience putting AI-enabled tools or processes into practice.
Collaborative Leadership Style
- Known for empowering specialized leaders (e.g., IT, data, engineering) through clarity of purpose and strategic alignment. Skilled at managing team dynamics with empathy and accountability.
Executive Communication and Influence
- Confident engaging with Board, CEO, and senior stakeholders on technology strategy, risk, and ROI.
Technical Breadth
- Familiarity with enterprise architecture, integration, and security principles to ensure alignment and scalability.
Professional Development
- Training in IT governance, risk management, and agile delivery.
- Certifications or coursework in change management, executive coaching, or user behavior analytics considered an asset.
Additional Notes
We use automated tools, including artificial intelligence, to assist with the initial screening of applications. All hiring decisions are ultimately made by a human reviewer.
Butterfield & Robinson is an equal opportunity employer committed to creating a diverse and inclusive environment. We consider qualified applicants regardless of race, colour, religion, gender, national origin, sexual orientation, age, citizenship, disability, or gender identity. Accommodation is available on request for candidates taking part in all aspects of the selection process.
Compensation Range: $180,000 - $250,000
How To Apply
To apply, please send a cover letter and resume by email to: employment@butterfield.com