Software is usually considered enabler for innovation in education. Thus, it is necessary to investigate: What leads to innovation in education and which, therefore, should be considered in the development of educational software? How to support decision-making for choosing software to be used in teaching and learning? How to evaluate software that enables, transforms, or supports innovation in education? In order to answer these questions, a research work was conducted that resulted in an approach called DEISE, which is concerned with drivers that lead to innovation in education and indicators that measure the fostering of software to skills need to students for 21st century learning. Through a web system developed for technological support to the DEISE approach, a set of educational software was evaluated by educators and the results show the index of innovation in education for each evaluated software and a comparison between educational software of similar purpose.