While organizations strive to be ambidextrous to navigate the complexities of the VUCA world, their success depends on individuals’ ability to successfully adapt to global changes quickly. Ambidexterity entails two contradicting behaviors—exploration and exploitation. When we balance both—either as an organization or as an individual, we are more successful at facing the challenges the global markets bring. In this chapter, we delve into the world of ambidexterity within organizations and how it is supported by corporate learning. While corporate learning programs prioritize the accessibility and variety of learning methods over the strategic alignment of knowledge with business goals, we highlight the importance of providing knowledge and skills for individuals to increase capabilities required for innovation and efficiency that support the ambidextrous organization. We address the challenge of fostering ambidexterity at different organizational levels, focusing on the role of corporate learning in nurturing individuals’ ambidexterity across levels. We provide findings from different research streams and insights from practice, addressing individual ambidexterity and ambidextrous leadership. Real life cases particularly show, that ambidextrous CEOs can enhance ambidexterity across the organization, as they support corporate learning environments. Based on reviewed literature and practice, we provide a checklist for ambidexterity across organizational levels.