Henri Giscard d’Estaing, who became CEO of Club Med in 2005, expressed the need to strategically reposition the Club upon his arrival as the head of the Group. The CEO has launched a number of major “action cycles” to reorient the business and improve its responsiveness to changing markets. A major strategic repositioning has been carried out: a move “upmarket” of the Club and its infrastructures. A profound intraorganizational change followed. The Club underwent a profound cultural transformation from 2004 to 2018 to meet the expectations of a more elite clientele targeted by the Group. This case explains the innovative strategic initiatives taken by the CEO to propagate change with stakeholders, and challenges students to evaluate his decisions and actions.