PushTotalk was a novel idea that groomed under the visionaries of eFusion, to address the eCommerce communication hurdles and to enhance the web experience. PushToTalk was envisioned as a VoIP(voice over internet protocol) tool and was built upon existing hardware infrastructure that eFusion had developed to service the telecom market, this technology had extensive capabilities and functionality. The functionality was overwhelming and the Internet market had not taken the turn for the worse yet. There was in house technology that was capable of addressing the VoIP need and also team of enthusiastic people who had the expertise to build this tool to provide seamless customer service experience in a web based transaction. As PushToTalk came in to fruition, there were many challenges and hurdles that both the development teams and management had to experience. There was paradigm shift in terms of project management which was difficult for the teams. Management had to solve funding issues to just exist in the market. PushToTalk got acquired twice and there were challenges for everyone who was involved directly or indirectly as the management changed. This paper analyses the project management challenges faced by the organization while introducing a novel idea to a market that was itself emerging. All these issues regarding product, project, process, organization, lessons learnt and recommendations are presented in the paper.