The study illustrates the significance of the characteristics of the individual SME entrepreneurs and enterprises in the digital transformation of SMEs. Adopting a mixed-method approach, we conducted 18 qualitative interviews and collected empirical data from 369 Indian SME entrepreneurs. The findings evidence that the digital self-efficacy of SME entrepreneurs significantly influences the digital transformation journey of the firms, and that SMEs managed by a professional leader will score better in the digital transformation journey. The study observed a significant moderating influence of the entrepreneur's age and the firm's age between digital self-efficacy and digital transformation. Finally, we found a significant association between digital transformation and firm performance. The findings of our study offer essential insights to the technology providers engaged in designing customized solutions for SMEs, keeping in mind their individual characteristics. The results will also help policymakers in promoting digitalization in the SME sector.