This two-part case series follows the dilemmas that Mattijs ten Brink, CEO of Transavia, is facing at deciding which path he should lead his team, to keep their journey as an independent airline company going strong for a longer period of time. Transavia is a subsidiary of the Air France-KLM airline group, providing low-cost “point-to-point” flights to destinations in Europe, Africa and the Middle East. The company is facing stiff competition from other European low-cost airlines with larger fleets and lower cost bases, while its parent company restricts their growth potential by limiting the number of main departure hubs and by deploying a different brand strategy for their low-cost long-haul flights and local regional flights. CASE A sees Mattijs at a cross-road for deciding which software company to choose to build a new digital ecosystem for Transavia to provide its employees with accurate and real-time data at each customer touch point, so that they can make better informed decisions and offer their customers relevant services and sales throughout the entire customer journey. This would be one of the company’s biggest IT investments in its 50 years of existence and key to achieve their ambition of becoming Europe’s leading digital airline. Mattijs can take the short cut to improve his revenues faster and please his commercial teams, or take the long route to spend more time on building customized solutions and please his operations teams. Any decision will likely upset several of his team members, so Mattijs has a personal stake in making sure that he chooses the right path forward. Learning objective: CASE A: We observe an everyday situation for executives of selecting between two software companies. There is not one obvious choice and everyone is looking at the CEO to make the final decision for which he/she will also be accountable. In this case we learn about the different criteria the CEO can use to justify his/her decision and how effective decisions can be made.