KASSANDRA, Education Guide and Career Suggestion; is the application for SIT students to get the overview of student’s skills both hard skills and soft skills to know their strengths and weaknesses to improve career skills. KASSANDRA contains Education Guide for each SIT courses and Suggestion for 12 common IT career paths, also the overview of SIT student’s career trend to know what’s going on in IT labor markets. Moreover, we apply machine learning to predict student’s grade for the current semester by using item-based collaborative filtering techniques to develop predictive model. Let’s decide your future with our application, the best education guide for SIT students.