Director of Engineering - Booking Group

The Director of Engineering will lead the Booking engineering organization, ensuring teams deliver reliable, scalable, and customer-focused solutions while fostering engineering excellence. This role focuses on developing leaders, shaping technical strategy, and creating an environment where teams can innovate and perform at their best.

• Lead and grow multiple engineering teams, establishing clear priorities, goals, and operating practices.


• Develop and coach engineering managers and senior technical leaders to strengthen leadership capabilities across the organization.


• Drive engineering execution at scale while maintaining high standards for quality, reliability, and customer experience.


• Define and influence technical strategy, architecture direction, and long-term product evolution.


• Partner closely with Product, Design, and business stakeholders to align engineering initiatives with customer and company priorities.


• Promote AI-native engineering practices by integrating AI-assisted development workflows and modern software delivery approaches.


• Encourage experimentation, continuous improvement, and iterative approaches to product development.


• Build systems and processes that enable teams to move quickly while maintaining operational excellence.


• Support the expansion of products and capabilities to meet growing customer needs and business objectives.


• Advocate for customer-focused engineering decisions and ensure technical investments support long-term growth.

Requirements:

The ideal candidate is an experienced engineering leader with a strong background in scaling teams, building customer-focused products, and navigating complex technical environments. You should combine strategic leadership with hands-on technical understanding and a passion for modern engineering practices.

• 7+ years of experience leading engineering teams, including experience managing engineering managers and developing leadership talent.


• Proven track record of building and scaling engineering organizations through periods of significant growth.


• Experience leading teams responsible for high-scale products used by large numbers of customers.


• Strong understanding of software development practices, architecture, and technical decision-making.


• Ability to stay connected to technical challenges and support teams with informed engineering guidance.


• Demonstrated experience using AI tools, workflows, or agent-based development approaches to improve engineering productivity.


• Strong understanding of AI’s impact on software delivery, including concepts such as evaluations and AI-assisted engineering models.


• Experience translating technical strategies into clear business outcomes and communicating effectively with stakeholders.


• Strong product mindset with experience partnering across Product, Design, and business teams.


• Experience leading through experimentation, iteration, and continuous learning.


• Experience working in regulated industries such as healthcare or fintech is considered an advantage.


• Strong communication, coaching, and organizational leadership skills.

Benefits:

• Competitive compensation package:
  
  
  
  • Canada: CAD $228,000 to $370,500 annual salary range.
  
  
  • Opportunity for equity participation through a stock option plan.
  
  
  
  


• Remote-first work environment with flexibility to work from anywhere in Canada.


• Opportunity to lead high-impact engineering teams within a fast-growing technology company.


• Access to comprehensive benefits programs designed to support employees and their families.


• Professional growth opportunities through ongoing development and leadership support.


• Opportunity to shape engineering practices in an AI-driven technology environment.


• Collaborative culture focused on innovation, learning, and meaningful customer impact.


• Opportunity to work on products used daily by thousands of businesses and professionals.


• Supportive environment that values autonomy, ownership, and continuous improvement.