Persuasive information developed by smartphone applications is a potential tool that can be utilized in order to increase the effectiveness of the impact of pricing strategies on triggering sustainable travel mode choice behavior. In order to address the joint impacts of pricing strategies and persuasive information on habitual automobile commuters’ travel mode shift responses, a stated-preference survey was conducted in Beijing’s inner district, from which over 1000 responses were collected. Four separate multivariable multilevel logistic regression models were estimated for more and less habitual automobile commuters when subjected to congestion pricing and reward strategies. The model estimation results showed that the influence of persuasive information was more effective in promoting travel mode shifts among more habitual automobile commuters with regard to reward strategies compared to congestion pricing. The results also showed that the impact of sociodemographic characteristics, commuter travel characteristics, the amount of congestion pricing or monetary award, and types of persuasive information on travel mode shift decisions under these strategies were deemed to be significantly different between more and less habitual automobile commuters. These findings suggest that more effective reward strategies can be explored by providing personalized and differentiated travel feedback information (e.g., pollution emission information and physical activity information), particularly for less habitual automobile commuters. This study also provides some degree of insight regarding the question as to how to design future congestion pricing, i.e., with respect to formulating differentiated charge rates according to the travel characteristics of habitual automobile commuters, as well as in developing complementary persuasive information that focuses on addressing public acceptability and fairness rather than travel feedback information.