Why CISOs Fail 2e and The Security Hippie Set

Released in 2017, the first edition of Why CISOs Fail reimagined the role of the Chief Information Security Officer in a new and powerful way. Written to be easily consumable by both security pros as well as everyone who must deal with them, the book explores the different realms in which security leaders fail to deliver meaningful impact to their organizations, and why this happens. Its central thesis—that security is primarily a human behavioral discipline rather than a technology one—has been gaining increased attention as a core tenet of the field, and the book was ultimately inducted into the cybersecurity canon as a leading book on security management. In this freshly updated edition, Barak Engel adds new sections that correspond with the chapters of the original book: security as a discipline; as a business enabler; in sales; in legal; in compliance; in technology; and as an executive function. He explores new ideas in each operational area, providing essential insights into emerging aspects of the discipline. He then proposes two critical concepts for security management—the concept of "digital shrinkage" and the transition from CISO to CI/SO—that together offer a new paradigm for any organization that wants to become truly successful in its security journey. Why CISOs (Still) Fail is delivered in Barak's conversational, humoristic style, that has attracted a global audience to this and his other book, The Security Hippie. As he notes, the book's goal is to entertain as much as to inform, and he dearly hopes that you have fun reading it.

The Security Hippie is Barak Engel’s second book. As the originator of the “Virtual CISO” (fractional security chief) concept, he has served as security leader in dozens of notable organizations, such as Mulesoft, Stubhub, Amplitude Analytics, and many others. The Security Hippie follows his previous book, Why CISOs Fail, which became a sleeper hit, earning a spot in the Cybercannon project as a leading text on the topic of information security management. In this new book, Barak looks at security purely through the lens of story-telling, sharing many and varied experiences from his long and accomplished career as organizational and thought leader, and visionary in the information security field. Instead of instructing, this book teaches by example, sharing many real situations in the field and actual events from real companies, as well as Barak’s related takes and thought processes. An out-of-the-mainstream, counterculture thinker – Hippie – in the world of information security, Barak’s rich background and unusual approach to the field come forth in this book in vivid color and detail, allowing the reader to sit back and enjoy these experiences, and perhaps gain insights when faced with similar issues themselves or within their organizations. The author works hard to avoid technical terms as much as possible, and instead focus on the human and behavioral side of security, finding the humor inherent in every anecdote and using it to demystify the field and connect with the reader. Importantly, these are not the stories that made the news; yet they are the ones that happen all the time. If you’ve ever wondered about the field of information security, but have been intimidated by it, or simply wished for more shared experiences, then The Security Hippie is the perfect way to open that window by accompanying Barak on some of his many travels into the land of security.