Director of Engineering - Booking Group

Team: IT

Location: Canada

Commitment: Full-time

Workplace Type: remote

Accountabilities:

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.