Director of Engineering - Booking Group
No longer listedThis position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director of Engineering - Booking Group based in Canada.
This leadership role offers the opportunity to shape one of the most critical engineering areas within a high-growth technology platform.
You will lead multiple engineering teams responsible for building scalable products that directly impact daily customer and user experiences.
The role combines technical leadership, organizational development, and strategic thinking to help teams deliver high-quality solutions at scale.
You will mentor engineering leaders, strengthen team structures, and define modern engineering practices in an AI-enabled development environment.
Working closely with product and business stakeholders, you will influence technical direction and support continued innovation.
This opportunity is ideal for an experienced engineering leader who enjoys building teams, solving complex challenges, and driving meaningful impact.
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director of Engineering - Booking Group based in Canada.
This leadership role offers the opportunity to shape one of the most critical engineering areas within a high-growth technology platform.
You will lead multiple engineering teams responsible for building scalable products that directly impact daily customer and user experiences.
The role combines technical leadership, organizational development, and strategic thinking to help teams deliver high-quality solutions at scale.
You will mentor engineering leaders, strengthen team structures, and define modern engineering practices in an AI-enabled development environment.
Working closely with product and business stakeholders, you will influence technical direction and support continued innovation.
This opportunity is ideal for an experienced engineering leader who enjoys building teams, solving complex challenges, and driving meaningful impact.
Accountabilities:
- 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.
- 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.
- 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.
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.
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.