Director of Software Development

Introduction to the team  

The Checkout Engineering Organization at Expedia Group is looking for an accomplished and passionate technology leader to help shape and scale the future of our checkout experiences across VRBO and Brand Expedia. This is a unique opportunity to lead the development of robust, high-performing, and scalable applications that power the travel journeys of millions of users worldwide.  

 
As Director of Software Development Engineering, you will lead a growing organization of engineers and engineering managers, bringing strategic vision, deep technical expertise, and a strong commitment to delivering exceptional user experiences. You will drive multi-year technology roadmaps, influence decisions across multiple technical domains, and foster a culture rooted in innovation, collaboration, and operational excellence.  
This role is ideal for a hands-on, user-centered leader who thrives in dynamic environments, enjoys working autonomously, and consistently delivers results through strong execution and cross-functional partnership. You’ll have the opportunity to make a lasting impact on Expedia Group’s travel platform and play a key role in helping travelers create unforgettable memories.  

What Sets Us Apart  

• Global Scale: We operate a platform that impacts millions of users worldwide, enabling our travelers to successfully plan and book a trip.  

• Innovation-Driven: We thrive on solving complex challenges, continuously evolving our technology stack, and staying ahead in the fast-paced travel industry.  

• Collaborative Culture: Our geographically distributed team is empowered to drive high-priority initiatives independently while fostering a culture of collaboration, inclusivity, and shared success.  

In this role, you will: 

• Represent engineering in executive forums, cross-functional initiatives, product/engineering reviews, and the EG (Enterprise Group) community of practice 

• Build strategic relationships with cross-functional leaders across the organization to deeply understand business challenges and apply technology-driven solutions 

• Lead and mentor a diverse team of engineering managers and senior individual contributors 

• Build strong, inclusive teams while empowering leaders to foster a high-performance, growth-focused culture 

• Secure resources and remove barriers to support teams in adopting innovative approaches and achieving ambitious goals 

• Own architectural and technology decisions across multiple domains and product lines in partnership with domain architect 

• Champion scalable, resilient, and stable software architecture and guide teams toward adopting best-in-class engineering practices 

• Align technology strategy with customer needs and evolving business priorities, identifying unexpressed user requirements 

Experience and qualifications:  

• Bachelor’s degree with 12+ years, or Master’s with 10+ years, of experience in software engineering or a related technical field (or equivalent professional experience) 

• 5+ years of leadership experience, including managing multiple people managers and overseeing large, distributed engineering organizations (30+ team size)  

• Proven track record of building and scaling high-performing, inclusive teams; mentoring leaders and individual contributors within and beyond your direct organization 

• Demonstrated success leading multi-year, multi-product roadmaps and delivering complex, cross-functional programs across business units 

• Deep full stack technical expertise across multiple domains, with a strong ability to guide architecture, drive technology choices, and lead implementation across diverse stacks. Platform experience and mobile experience is a huge plus  

• Experience leading the development and evolution of critical, large-scale services, with a strong focus on stability, scalability, and quality 

• Excellent communication and stakeholder management skills; comfortable presenting complex technology decisions to both technical and non-technical audiences 

• Strong strategic planning and operational execution capabilities; adept at identifying organizational needs and implementing process and cultural improvements 

• Passionate about customer-focused innovation and delivering technology solutions that solve real business problems