The predominant ethical focus of business as perceived by citizens and consumers, along with the leadership demands placed on companies and brands by Generation Z and Light Millennials, serve as the foundation for this volume. Companies that are able to combine influence, credibility, and charisma into a global and local “human touch” will win the challenge. For this reason, CEOs must know how to transform themselves from seducers to pioneers: companies, and no longer just NGOs or parties, are seen as the engine of sustainable change. This work combines a theoretical framework for successful reputation management models with extensive pragmatic research. Insights from 15 Italian CEOs and 14 international CEOs illustrate how they have addressed reputation challenges with strategic and adaptive approaches. In addition, two field studies show that small and medium-sized enterprises and talent acquisition are critical focal points for developing response strategies to market demands and stakeholder expectations. An essential and complete guide for executives, C-level and senior managers aspiring to the role of CEO, those supporting them in brand building, and those studying market entry strategies.