The on-premise point of sale (POS) system has been using by retailers for years. However, this system causes some user pains and problems, i.e. high capital investment, setup and maintenance hassle, lack of flexibility and reliability, and data security and privacy concern. Cloud computing as an emerging technology is used for developing a cloud-based POS software named RetailNow. A cloud service provider is in charge of delivering and maintenances of the software to retailers based on their environments. The provider is also responsible for security and privacy of data on its servers. Due to the pay-per-use subscription model of the cloud, retailers also save in their finance. The retailers only require a basic computer and an internet connection in order to connect to RetailNow. RetailNow is targeted for all scales and environments of retail outlets. The purpose of the study is to understand the influential factors that impact on intention to use RetailNow among retailers in Malaysia. The proposed model is the combination of the TOE and the TAM to obtain applicability and predictive power. In order to test the proposed model, a quantitative study using a self-administrated survey will be directed. A research method which is based on the multi-analytical approach of Partial Least Squares Structural Equation Modeling (PLS-SEM) and Artificial Neural Networks (ANNs) is applied which enables extra verification of the results provided by the PLS-SEM for direct relationships in the model. We only apply PLS-SEM for testing the mediation effect.