Stiff competition in the Airline sector mandates airlines to innovate ways to gain a competitive advantage over their rivals; however, without a strong IT the mission to attain this would be arduous. Large airlines do their best to maximise the use of enterprise systems to stream their business processes. Nonetheless, some airlines are not up to date with technology and are left with few choices when attempting to secure their existence in today’s harsh market. One option is to implement bleeding edge systems concurrently (which is our focus in this paper) due to the fact that very scant research exists regarding this phenomenon, let alone the airline sector itself. The aim of this study is explore and investigate the phenomenon of deploying multi enterprise systems concurrently due to its uniqueness and owing to the fact that this approach is not the common practice most airline undertake. We argue here that having multi Airline Solution Providers (ASP) working together concurrently to constitute a homogeneous solution generates many aspects that necessitate a deep understanding in such matters as competitor ASPs and technology leakage. In addition, the study explored various themes that unleash the phenomenon of the concurrent Multi- collaborative Enterprise Systems (MES). The role of cohesion factors that groups the rivals to work under the umbrella of an organisation was also embarked upon in this study. Various aspects contributing to the success of the MES phenomenon have been exposed with regarding ASP’s interplay, organisation, and other contextual surrounding MES. Finally, this study drew a strategic frame work for airlines that unleash the MES phenomenon. A large airline and its collaborative airline solutions provider were taken as the scope of study; the airline had over twenty six thousand employees. Five reputable world class ASPs in the airline industry in various fields were also included. The twenty five participants in this study were professionals in IT and the airline business besides being involved heavily in the phenomenon of deploying concurrent multi enterprise systems. Grounded Theory techniques were used to analyse the large volume of data gathered underpinning this by using state of art software package such as nVivo. This research has explored the phenomenon under study using grounded theory methodology to build a theoretical model that best presents the MES initiative. In addition, it has offered a well-founded framework that explains the MES phenomenon in details, which is relevant to both practitioners and researchers. This research has clearly explored and demonstrated the inhibitors and enablers in the undertaking of MES. In particular, it has focused on enablers of the organisation that received the MES. Furthermore, it has explored the interrelationship between ASPs and exposed some of the aspects that need more focus between rivals working on the same project.