Digitalization is incrementally transforming business practices, particularly in sales and digital marketing, although the factors motivating entrepreneurs to adopt digital technologies in sales strategies remain underexplored. Consequently, the aim of our research is to identify the factors that influence the use of digital technologies in sales. This research elucidates the interplay between demographics and entrepreneurial motivations, utilizing data from the Global Entrepreneurship Monitor, involving 464 entrepreneurs in Slovenia and Croatia, analyzed through logistic regression. Notably, demographic factors, including gender, age, and education, do not significantly influence digitalization adoption in sales strategies. Among entrepreneurial motives, only the aspiration “to make a difference in the world” propels entrepreneurs towards considering digital sales approaches, while other motivations do not have a significant influence. Despite extensive studies on demographic factors influencing digital technology adoption, a consistent trend is conspicuously absent, necessitating an intricate examination of various dimensions of digital business transformation. Furthermore, our findings underscore that, while digitalization is acclaimed for enhancing companies’ profitability, entrepreneurs motivated by altruistic goals demonstrate a pronounced proclivity to integrate digitalization into sales, signifying that digitalization’s pragmatic utility extends beyond merely amplifying profitability and growth, insinuating a more integrative role in sculpting sustainable entrepreneurial practices and business models.