The research study was designed to examine the degree of perceived skill level of utilizing Web 2.0 technology applications among certified education professionals. In addition, this research study was designed to examine differences among various groups as well as reasons for these differences. Furthermore, the Web 2.0 applications presented in the survey were linked to the International Society for Technology in Education’s National Educational Technology Standards and presented to participants to increase knowledge of Web 2.0 technology applications. The population included all certified education personnel at 34 schools. The perceived skill level of business educators as compared to all educators was significant and the overall sum score mean was one of the highest reported in this study. All educators reported a higher skill level for events and social networks. Business educators perceived a higher skill level for cloud computing; whereas cloud computing was a reported lower skill level for overall certified participants.