Along the path of 4th industrial revolution, industries are expanding and increasing reliance on technology solutions. The security profession is one of those industries which has been on a global quest to increase reliance on technology while obtaining higher resilience, maintaining efficiency and financial prudence. This has demanded security leaders to seek creative ways of transforming and scaling operations through unprecedented endeavors in the technology domain, as well as major investments into technology and cyber assets. In recent years, Digital Transformation (DT) became vital for the business. However, this drastic change emerged with new type of risks, mainly in change risk. The newly rising risks introduce a new set of vulnerabilities and complications that may go unnoticed by business leaders. This speech will shed light on digitalization change risks and challenges that must be considered, analyzed and mitigated early on during initiation and planning of digital transformation journey. The purpose is to assure a higher caliber of success by security professionals and leaders as well as to avoid obstacles and issues during implementation and operation. The speech will also discuss a set of mitigations and strategies proven successful in handling and overcoming the risks during transformation while capturing valuable lessons-learned.