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Advances in innovation and technology have become a main point of interest for researchers in the field. Previous researches show high dependence of the tertiary sector upon strategy, together with lagging digitalization in European economies. This to gain insight into digital innovation strategy and actual technological implementation within companies in South-Eastern European economies. The study employs a mixed-method approach, combining both qualitative/quantitative methods. It was carried out through structured interviews. These interviews involved the use of a straightforward assessment tool to collect quantitative responses along with qualitative justifications for those responses. In total, we collected 102 validated interviews from various company managers, ensuring that no more than one assessment per company was included in our analysis. Results show deficiencies in some managers' understanding of digital strategies cascading down to insufficient or improper usage of technological tools to implement digital innovation. Initiatives in combating lagging digitalization should thus contain a significant educational component for managers and decision makers. [ABSTRACT FROM AUTHOR]