The process of globalization and the changeability of environment nowadays demand that society ensure sustainability for itself and its lifewide environment. Therefore nowadays the paradigm of personality's and specialist's competitiveness is changing. The old paradigm is substituted by a set of new viewpoints and concepts. The issue of ensuring the environment fostering the development of specialists competitiveness in the modern enterprise becomes even more important. Research in this sphere had three stages: 1) development of theoretically-methodological base for specialists' competitiveness research; 2) diagnostics and evaluation of the specialists' competitiveness in modern insurance enterprise (experimental approbation of the competitiveness research methodology); 3) development, evaluation, improvement of "The Model for Evaluation, Support and Promotion of the Staff's Competitiveness Development in Modern Enterprise as Learning Organization" and its offer for implementation into research base-insurance enterprise. The objectives of research: 1) to investigate the specialists' "competitiveness" in the modern insurance enterprise; 2) to develop and evaluate "The Model for Evaluation, Support and Promotion of the Specialists's Competitiveness Development in Modern Enterprise as Learning Organization" in the contexts of information and knowledge society and sustainable development.