This paper examines the impact of top management transformational leadership on supply chain organizational learning and supply chain ambidexterity. We also evaluate the influence of uncertainty, present in the operating environment, on these relationships. Integrating multiple perspectives of organizational behavior relating to learning and leadership, we develop our research model and evaluate it using survey data. Results from our analysis support the notion that supply chain organizational learning orientations fully mediate the relationship between transformational leadership and supply chain ambidexterity. Also, uncertainty in the operating environment positively moderates the relationship between transformational leadership and supply chain learning.