Maya Leibman, the Executive Vice President and CIO of American Airlines, recently shared her insights on her 27-year career at the airline, her successes and learnings along the way, and what it means to be the "air traffic controller" of American Airlines' technological transformation. She discussed how COVID impacted her approach to technology innovation, empowering different teams, and measuring their innovation, as well as her leadership style evolution over time. Maya also shared lessons learned from the JetStream Program, a project that she described as a disaster, but which taught her the importance of developing an experimental mindset and being willing to pivot when necessary. Additionally, she offered advice on how women can overcome difficult conversations and negotiations on topics like salaries, and reflected on the biggest challenge in her career, which was the merger between American and US Airways, and how she overcame it by assuming positive intention.