The nature of the enterprise and working is rapidly changing. Recognizing the enabling competitive advantage of new social and participative technologies will transform the enterprise. Web 2.0 is the foundation of the new Enterprise 2.0. By accessing the right information at the right time, Enterprise 2.0, through a web of interconnected applications, services, and devices, provides capabilities for employees to be more competitive and productive and for customers to be more engaged and loyal. Enterprise 2.0 CIO management issues include unauthorized use of enterprise services and technologies, the integration of a myriad of technologies, and potential compliance and security implications. This paper describes an ongoing case study evaluating a conceptual framework exploring relationships among three Enterprise 2.0 dimensions: technology tools and capabilities, employee and customer applications, and how user-generated content leads to business value. It is expected that this qualitative study will also identify new IT culture and policies.