Digitalization is rapidly advancing and becoming a social and business sensation.  Digitalization is stimulating the escalation of 3D printing, artificial intelligence, Internet of things and Big Data, to name a few.  This paper establishes the extent to which a South African (SA) private organization is prepared for, or has adopted the digital era, and the challenges that have been experienced by implementing digitalization, which is now becoming a major component of the business environment. The study is also intended to create awareness and prepare the organization as well as its stakeholders for this new digitalization era. A mixed method research approach was adopted.  The researcher has selected a simple random sample of 50 employees to complete the research questionnaire.  It was established that there were several barriers such as an improper digital strategic plan, stakeholder engagement and lack of communication, which tend to inhibit the digitalization process.  Additional concerns at the SA private organization that inhibited the digitalization process was the flow of information among all stakeholders concerned, regarding digital strategy such as employees, suppliers, customers and the management.  Digitalization delivers a plethora of benefits and improves the way in which organizations engage with its customers.