The advent of the Internet and the World Wide Web has been instrumental in bringing about the growth in the implementation of web-based information systems (WBIS). Such systems are designed with the aim of improving productivity, data accuracy, and the reduction of paperwork and administrative overheads. Moreover, unlike their conventional non-web-based predecessors, the WBIS are commonly aimed at users who are casual and untrained, geographically distributed and non-homogenous. The dissemination of WBIS necessitates additional infrastructure support in the form of a security system, workflow and transaction management, and web administration. WBIS are commonly developed using an evolutionary approach, whereby the version of the application, acquired from the vendor, is first deployed as a pilot, in order to gather feedback from the target users before the evolutionary cycles commence. While a number of web development methodologies have been proposed by existing research, there is a dearth of empirical evidence that elucidates the experiences of project initiators in pursuing the evolution of web services, a process that undoubtedly involves dealing with stakeholder issues. This research project presents a phenomenological investigation of the experiences of project managers with the implementation of web-based employee service systems (ESS), a domain that has witnessed a sharp growth in Australia in recent times. However, the project managers’ rich, multidimensional account of their experiences with the implementation of ESS revealed the social obstacles and fragility of intra-organizational relationships that demanded a cautious and tactful approach. Thus, the study provides a socio-organizational perspective to web projects in contrast to the functionalist paradigm of current web development methodologies. The research also confirms that consideration of the concerns of stakeholders by project managers is crucial to the successive cycles of ESS evolution. Project managers address stakeholder concerns by pursuing actions that are aimed at encouraging ESS usage, but at the same time, such actions can have consequences necessitating subsequent iterations of system enhancement and improvement. Finally, the research also discovered that despite the different socio-political climate prevalent in various organizations, in which ESS are being implemented, the experiences of project managers in dealing with stakeholder concerns can be captured and independently confirmed in terms of their perceived relevance and usefulness in problem-solving within the application domain.