The objective of this study is to gain a clearer understanding of the role Persuasive Experience (PX) may play in wellness-oriented Web Based Learning (WBL) platforms in forming abilities to incite healthier lifestyle (or promoting health behavior) in technology-based systems use. Specifically, individual users’ interactions with a particular corporate wellness WBL platform was examined in relation to their State of Mind and Behavior. The results of this study may assist in better predicting behavior change and sustainable adherence to increased physical activity routines that could reduce risk of behavior sensitive conditions such as cardiovascular disease and its sequelae in U.S. workplaces. The findings of this case study also offer further validation of PX Theory and insight into its potential to aid in developing and implementing more effective persuasive technologies. The hope is that PX might contribute to technological systems design that can measurably and meaningfully assist employees in changing to healthier behaviors to improve their individual health outcomes. The results of this case study also suggest the potential PX driven design for wellness oriented WBL systems may have in improving overall organizational wellbeing and outcomes related to unplanned health insurance expenditures.