In this paper, we explore user reactions to prototypes that integrate population fitness data with personal practice to bolster motivation and help decrease pragmatic barriers to incorporating exercise in daily life. We conducted a study in a major United States based company that makes wearable devices available to their employees through its wellness program. We interviewed each of 26 employees to understand their exercise and tracking habits. Each expressed an interest in improving or maintaining his or her fitness level but was frustrated by not getting appropriate support from the current Fitbit application. Based on the interview findings, we designed four use cases and two prototypes to address the main problems revealed through analyses of the participants' interviews and their Fitbit data. In a second interview probing reactions to they prototype, the same group of users reported a desire for Fitbit to support their daily, dynamic routines and to help them make adaptive, weekly plans. In addition, the participants perceived benefits to leveraging at least one of three different types of personalized reference groups (self, friends, or a population of similar individuals) to increase their motivation and to help incorporate activities into their daily or weekly plans. We discuss design consideration for researchers and designers of personal informatics tools and organizational wellness plans.