The fast development of technologies shapes the way companies address and understand their customers’ needs, including the more and more pressing call for sustainability. If, by now, many organizations use the advantages of social media in their marketing strategies, newer technologies, such as Internet of things (IoT) wearables, are not fully used to their whole potential. Thus, we conducted two research studies—a qualitative one in the form of a focus group where eight different companies’ representatives took part, followed by a quantitative one in the form of an online questionnaire, where 84 (Small and Medium Sized Enterprises) SMEs and Large Enterprises answered. The main purpose of our research was to investigate companies’ attitudes and practices about using social media and IoT wearable technologies in developing organizational marketing strategies. The results indicate that, though there are some differences in the perception and use of social media and IoT wearables for developing marketing strategies, these differences are not marked between SMEs and Large Enterprises, but rather between micro enterprises and other companies with higher numbers of employees. Additionally, there are some differences noticed between companies operating in regional, national, or international markets.