As smart technology proliferates, enterprises must engage not only in the transformation of intelligence but contend with pressure do so as soon as possible. Smart transformation is critical for manufacturing enterprises in the development of smart manufacturing. This study addressed the gap between maturity models and project management by designing an effective assessment framework for smart transformation. It adopts the Smart Industry Readiness Index, created by the Singapore Economic Development Board, as a maturity assessment model to analyze enterprises’ smart transformation and formulate project management strategies. Enterprises can use this model to examine the maturity level of their transformation and assess scope for improvement in their project strategies and implementation barriers. This study focuses on Taiwanese enterprises using data collected from 165 valid questionnaires and subjected to a cluster analysis. Enterprises were divided into three categories. The results reveal that, first, most enterprises’ smart transformation is at an immature or medium-maturity level, and is therefore amenable to further improvement. Second, inconsistent with research findings, many enterprises invest in transformation projects but fail to advance these projects to maturity. Third, most enterprises’ project management plans fail to meet actual transformation needs. Using the thematically oriented maturity model proposed in this study, Taiwanese enterprises can effectively evaluate the maturity of their transformation projects. In conclusion, the study highlights that Taiwanese enterprises must identify more effective external resources to strengthen their competitiveness.