The arrival of social and collaborative software applications (e.g. Facebook, Hyves, and LinkedIn), known as Web 2.0 applications, has provided an opportunity for customers to express their opinions and share their knowledge and thoughts with others. While customers use Web 2.0 applications on daily basis, companies are struggling to embrace fully functioning Web 2.0 applications for their business. An organization that is able to successfully select, facilitate, and utilize appropriate Web 2.0 technologies and applications is called Enterprise 2.0. There is an enormous social pressure on organizations to adopt Web 2.0 technologies and become Enterprise 2.0 as quickly as possible if not now. Based on six cases, the paper as an exploratory research will provide immediate actions organizations can take to move toward Enterprise 2.0 by recommending Web 2.0 tools they can adopt and some aspects they should consider in changing organizational internal conditions to support Web 2.0 activities.