This paper aims to test an artificial model and a calculator the author developed based on deep learning, Neural Networks, and machine learning, Random Forest. The “Diab BITA Model” and the “Diab Calculator” are generated to enable organizations of any size and in any industry, of calculating the value of Strategic Business-IT Alignment (BITA) following a scale of 7 degrees. Principally, the same sample of one of his previous papers is addressed in which top Managers subjectively assessed the BITA maturity; the current paper targets to empirically prove the accuracy of managers’ perceptions using both the model and the calculator. Findings show an 89% accuracy rate in estimating those organizations’ BITA levels using the model and 92% using the calculator.