Leadership is undoubtedly a complex topic mainly because this is about human behaviors, attitudes, motivations, historical moments, preferences, and particular reasons to lead in one or another way. The subject of cybersecurity is problematic by itself because of all the ramifications, inclusions, obscurity, lack of knowledge to truly understand the possible consequences of insecure actions when working with information systems, frustrated employees, "bad" actors around the world motivated by multiple reasons from financial gain to a particular kind of ideology; the tremendous and growing amount of misinformation in social media about information security, dogmas, unbiased repetition of what others said, and a mounting number of different technologies used at the workplace. For all these reasons and many others, cybersecurity leadership in the 21 century is even more complicated and a very poorly developed topic. It was the primary motivation for this book. This volume is the very first in approaching the specific topic of leadership in cybersecurity. It proves that those individuals that believe they can make informed decisions based on social media and/or internet findings are putting their organizations at risk, unintentionally or not. An old saying says, "I don't need to know how each instrument is played to be the director of the band," is obsolete and in complete opposition to what is required today to minimize the possibilities of security breaches at your place of work. Cybersecurity leaders need to master the topic or relies on those than do, but the opposite position is well rooted, even taught at many levels and educational institutions. 2020 will be remembered for years to come as the "pandemic year." The world was not prepared for, neither the workforce. The COVID-19 crisis dramatically increased telework, and the majority of the organizations worldwide were required to rapidly adapt to the new reality; work from remote locations. The traditional office rapidly and unexpectedly becomes virtual, and people historically custom to work physically close, found their-self working as part of virtual teams, geographically segregated, and with that, with those "simple" ups and downs, cybersecurity becomes one of the biggest challenges on the 21 Century related to survival and competitiveness at the corporate level. Previous to the crisis, the topic of leadership in cybersecurity was already under exploration because of the prominent role of informatio