Introducing Artificial Intelligence (AI) into commercial air transport operation is expected to remarkably impact future roles by 2050. This paper introduces the results of the EU Horizon Project HAIKU, where a series of workshops and interviews were conducted with subject matter experts (SMEs) in aviation to explore the key milestones in the evolution of human roles in industry. Furthermore, the paper presents the likely changes required by personality traits, skills and training through the example of commercial airline pilots, as one of the key roles impacted the most by the introduction of artificial intelligence in operation.