Considering the advancing digitalization and the rise of new technologies, the way people interact with one another but also approach companies has fundamentally changed. In this respect, chatbots have experienced a “comeback” recently and many large companies but also small and medium-sized enterprises (SMEs) in the B2C sector search for ways to support the conversation with customers via chatbots. Nevertheless, chatbots must fulfil particular functionalities (e.g., in terms of language processing or quality of communication) to be purposefully applied in an entrepreneurial setting, and particularly, at SMEs. The investigation at hand analyses the solutions of 14 technology providers for realizing a chatbot in terms of (1) quality of the communication, (2) reaction to inappropriate input, (3) personalization, (4) language processing, (5) security, (6) interfaces & mobile device support, (7) training, (8) implementation and (9) costs. Thereby, the peculiarities of human-machine communications and requirements of firms are taken into account. The results were derived on base of an online survey among the solution providers. It turned out that a high percentage of the functionalities, which are decisive for a valuable entrepreneurial chatbot application, are covered by the providers, however, with nuanced differences being observed regarding particular features.