Through qualitative research, few things can be implied theoretically and managerially. The research finds that digital transformation in hotel revenue management is executed on the different levels of sophistication. Besides the cost of RM-specific software, there are other key barriers such as divergent perspectives among RM managers, senior management, and market size. Also, the research analysis confirms that the sophistication of RM Software could create several benefits easing RM managers’ responsibilities while the human aspects of RM will still win the technical innovation and software support system. Based on the interview result with the revenue managers in upscale hotels, it seems like RM in hotels has become more complicated and highly technology-driven. Therefore, it is required for academic sides to implant this contemporary progress on the technology to the RM program. Also, due to the relatively high cost of RM software, it is recommended for the software companies to offer varied products for targeting different hotels with a variety of options. For developers, it is recommended to consider extending the range of their RM software to F&B and functions area to pursue extra revenue.