Determining how notions of digital books influence digital divide and decision-making for organisations is problematic, not least because it is an evolving concept, rooted in consumer and organisational awareness in relation to levels of technological adoption. The concept represents a phenomenon that is elusive and prone to misconception. This paper examines how individual choices about IT products impact on social conceptualisations concerning rapid diffusion of information and utilisation of technological innovations. A two-stage research design solicited perspectives regarding online marketing challenges to marketing in the bookstore industry. Themes emerged that were developed into a conceptual model. It is suggested that firms must manage different customer segments through different value propositions, based on a multidimensional segmentation scheme that recognises the dynamic nature of value and value propositions to help managers classify customer portfolios and create effective value propositions.