The advent of the World Wide Web (WWW) and the emergence of Internet commerce have given rise to the web as a medium of information exchange. In recent years, the phenomenon has affected the realm of transaction processing systems, as organizations are moving from designing web pages for marketing purposes, to web-based applications that support business-to-business (WEB) and business-to-consumer (B2C) interactions, integrated with databases and other back-end systems (Isakowitz, Bieber et al., 1998). Furthermore, web-enabled applications are increasingly being used to facilitate transactions even between various business units within a single enterprise. Examples of some of the more popular web-enabled applications in use today include airline reservation systems, internet banking, student enrollment systems in universities, and Human Resource (HR) and payroll systems. The prime motive behind the adoption of web-enabled applications are productivity gains due to reduced processing time, decrease in the usage of paper-based documentation and conventional modes of communication (such as letters, fax, or telephone), and improved quality of services to clients. Indeed, web-based solutions are commonly referred to as customer-centric (Li, 2000), which means that they provide user interfaces that do not necessitate high level of computer proficiency. Thus, organizations implement such systems to streamline routine transactions and gain strategic benefits in the process (Nambisan & Wang, 1999), though the latter are to be expected in the long-term. Notwithstanding the benefits of web technology adoption, the web has ample share of challenges for initiators and developers. Many of these challenges are associated with the unique nature of web-enabled applications. Research in the area of web-enabled information systems has revealed several differences with traditional applications. These differences exist with regards to system development methodology, stakeholder involvement, tasks, and technology (Nazareth, 1998). According to Fraternali (1999), web applications are commonly developed using an evolutionary prototyping approach, whereby the simplified version of the application is deployed as a pilot first, in order to gather user feedback. Thus, web-enabled applications typically undergo continuous refinement and evolution (Ginige, 1998; Nazareth, 1998; Siau, 1998; Standing, 2001). Prototype-based development also leads web-enabled information systems to have much shorter development life cycles, but which, unlike traditional applications, are regrettably developed in a rather adhoc fashion (Carstensen & Vogelsang, 2001). However, the principal difference between the two kinds of applications lies in the broad and diverse group of stakeholders associated with web-based information systems (Gordijn, Akkermans, et al., 2000; Russo, 2000; Earl & Khan, 2001; Carter, 2002; Hasselbring, 2002; Standing, 2002; Stevens & Timbrell, 2002). Stakeholders, or organizational members participating in a common business process (Freeman, 1984), vary in their computer competency, business knowledge, language and culture. This diversity is capable of causing conflict between different stakeholder groups with regards to the establishment of system requirements (Pouloudi & Whitley, 1997; Stevens & Timbrell, 2002). Since, web-based systems transcend organizational, departmental, and even national boundaries, the issue of culture poses a significant challenge to the web systems’ initiators and developers (Miles & Snow, 1992; Kumar & van Dissel, 1996; Pouloudi & Whitley, 1996; Li & Williams, 1999).