Through the microfoundation lens, this article explores how dynamic capabilities (DCs) of Chief Digital Officers (CDOs) trigger digitalization and organizational creativity of 2124 small to medium enterprises (SMEs) across 39 different European countries. As a result, the significant DCs are substantive and adaptive capabilities, which are offering new solutions, seizing new opportunities, and coping with changes. Besides, those two DCs also assume a mediator role in triggering organizational creativity within SMEs. In terms of theoretical and managerial implications, threefold contributions are provided: the first one offers a fresh study on the digital transformation context of SMEs through a microfoundation perspective; the second emphasizes the crucial role of CDOs as supported and remarked upon previous studies; and, then, the third one stresses out the importance of the individual leverage to generate creativity by the moderating role of DCs. By highlighting the originality of the research, since CDOs are seen to be the spark of unique ideas and innovations in the organization, further insights are proposed to position the need for conceptualizing new paths for developing technologies toward organizational creativity and humanity.