Effective up-skilling teachers who are involved in teaching software engineering should take into account the challenges of teaching practice. Despite the long practice of organizing the teaching of software engineering and computer science in educational organizations in Russia, relevant up-skilling courses are not methodologically supported. The paper introduces an active, practice-oriented approach to organizing up-skilling courses for teachers who teach software engineering and development. The authors developed the level model for the advanced up-skilling teachers interested in mastering and delivering modern technologies of Agile software engineering and development. Authors implemented the model for organizing teachers’ up-skilling courses in intensive schools for engineering, development, design and management of software products