How AI will change travel booking with Trainline's Gary Stevens

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Trainline's Gary Stevens discusses leading engineering teams, building customer trust in AI-powered rail booking, and evolving from hands-on coding to enabling team success.

Key takeaways
  • Team engagement is a top priority, focusing on ensuring engineers feel their work has impact and meaning while maintaining clear goals and metrics

  • Rail travel technology faces interesting challenges around aggregating routes across Europe, multimodal journey planning, and integrating machine learning/AI while maintaining customer trust

  • Leadership approach emphasizes coaching over direct problem-solving - learning to “put down the pickaxe” and enable teams to find solutions themselves while providing support and guidance

  • Regular team showcases led by individual contributors help celebrate wins, share knowledge, and give visibility to different team members’ work, especially for remote teams

  • Customer trust is vital - being transparent about how recommendations and decisions are made, particularly when implementing AI/ML features

  • Focus on sustainable transport and improving the rail booking experience through better data, simplified UX, and transformative product features

  • Career progression from individual contributor to director required shifting mindset from hands-on problem solving to enabling and developing others

  • Measuring success through engagement metrics while being careful about potential negative effects of focusing too heavily on single metrics

  • Importance of creating space for teams to try things and potentially fail while providing appropriate support and guidance

  • Staying current with rapidly evolving technology landscape (especially frontend) requires balance between hands-on knowledge and trusting team expertise