Economies suffering from increasing inflation and unemployment rates may witness attempts of individuals turning to available Incubator/Accelerator programs to raise support for their early stage start-up ideas, of which many are digital-first with high-risk yet relatively low capital requirements. In order to increase chances of being selected among the country’s and sometimes the region’s top start-up ideas, entrepreneurs must present strong and thorough business proposals. Besides the market feasibility and the projected financial returns, these proposals should cover a coherent implementation approach which often outlines the design of the proposed digital platform, including aesthetics and functionality. The purpose of this research is to examine the importance of aesthetic design, functionality of the design of e-commerce websites, as well as m-commerce applications. Based on in-depth literature review, and using the theory of “form and function” (Townsend et al., 2012) and Cebi’s hierarchy of design characteristics (2013) as a theoretical framework underpinning this study, the authors explored the various aspects of design and functionality that may affect performance measures and hence allow e-commerce companies to better recognize what needs improving. In light of this analysis, a model was developed that showed the relationship between aesthetics and functionality of website/mobile app design on one hand, and the customer journey on the other.  Analysis of a website and a mobile app showed that trust and reputation are factors that influence the expectations and impressions of both the aesthetic and functional designs. Moreover, aesthetics act like a façade, that either initiate or annihilate the customer journey, and in the case of passable aesthetics, functionality becomes the key player of the journey. The implications of the study are discussed, and the limitations and recommendations for future research are presented.