Director of Engineering - Booking Group

Role Overview

We are seeking a Director of Engineering for the Booking Group based in Canada. This senior leadership role is pivotal in shaping essential engineering functions within a rapidly expanding technology platform. The position involves overseeing multiple engineering teams that develop scalable products directly impacting user and customer experiences daily.

Key Responsibilities

• Lead and expand several engineering teams with well-defined priorities, objectives, and operational standards.
• Mentor engineering managers and senior technical leads, enhancing leadership skills throughout the organization.
• Ensure engineering excellence by steering execution at scale while upholding quality, reliability, and a customer-centric approach.
• Establish and guide technical strategies, architectural directions, and long-term product evolution plans.
• Collaborate intimately with Product, Design, and business stakeholders to synchronize engineering projects with corporate and customer priorities.
• Promote AI-native engineering processes, incorporating AI-assisted development methods and modern software deployment practices.
• Encourage continuous improvement through iterative experimentation and agile product development techniques.
• Develop systems and workflows that empower teams to deliver rapidly without sacrificing operational quality.
• Support product and capability growth to meet expanding client requirements and business goals.
• Champion engineering decisions that prioritize customer needs and align technical investments with sustained growth.

Candidate Requirements

• Minimum of 7 years leading engineering teams, including supervising engineering managers and fostering leadership development.
• Demonstrated success in scaling engineering organizations during significant growth phases.
• Experience managing teams responsible for high-volume products with extensive user bases.
• Deep knowledge of software development methodologies, system architecture, and technical decision frameworks.
• Ability to remain engaged with technical challenges and actively support teams through informed guidance.
• Hands-on experience leveraging AI tools, workflows, or agent-based software development techniques to boost engineering productivity.
• Understanding of AI’s role in software delivery, including evaluation frameworks and AI engineering models.
• Proficient at translating technical strategy into measurable business results and communicating clearly with all stakeholders.
• Possess a strong product orientation with experience collaborating cross-functionally with Product, Design, and business units.
• Track record of leading teams through experimentation, iteration, and ongoing learning processes.
• Experience in regulated sectors such as healthcare or fintech is advantageous.
• Excellent communication, coaching ability, and organizational leadership skills.

Compensation and Benefits

• Competitive annual salary between CAD 228,000 and CAD 370,500.
• Potential equity participation through stock option plans.
• Remote-first workplace with flexibility to operate anywhere within Canada.
• Chance to lead impactful engineering groups within a fast-growing tech firm.
• Access to broad benefits packages supporting employees and their families.
• Opportunities for professional growth through continuous development and leadership mentoring.
• Engage in defining engineering processes within an AI-driven technology environment.
• Work culture emphasizing innovation, learning, and meaningful user impact.
• Product involvement used daily by thousands of businesses and professionals worldwide.
• Environment that fosters autonomy, ownership, and a focus on ongoing enhancement.

Additional Information

This vacancy is managed by an external partner company which handles applications and subsequent recruitment steps. The application review process utilizes AI technology to evaluate candidates impartially and identify top matches. Final hiring decisions rest with the internal hiring team.

Data Privacy Notice: By applying, candidates consent to the processing of personal data for recruitment purposes. AI tools may assist in application analysis, but human judgment governs final decisions.