This chapter attempts to assess the impact of various factors and characteristics on B2B advertising effectiveness. The main focus of the authors is print ad effectiveness given the lack of adequate relevant research and the concurrent need for economical and efficient use of the traditional tools that are reported to be losing ground against digital ones. While there is no doubt that advertising is becoming increasingly important in B2B, managers are becoming more skeptical about the use of print media, partly because of the absence of immediate results and apparent merits deriving from B2B print advertising. As such, the authors aim to contribute to the extant literature by offering some empirical data and some suggestions on how to increase print advertising effectiveness in B2B.