As the Indian retail sector undergoes rapid digital transformation, the role of frontline employees in adapting to emerging technologies has become increasingly critical. This study examines the readiness of retail employees in Jodhpur, Rajasthan, toward digital transformation by analysing key influencing factors: digital competency, organizational support, training and development, and attitude toward change. Drawing on data from 200 respondents across various organized retail outlets, the research adopts a quantitative methodology using PLS-SEM to evaluate hypothesized relationships among these constructs. The results indicate that digital competency is the most significant predictor of readiness, followed by attitude toward change, training initiatives, and organizational support. The model explains 63.8% of the variance in employee readiness, suggesting that both individual capabilities and organizational interventions are vital for successful digital adoption. Measurement and structural model assessments demonstrate strong reliability, validity, and model fit indices (SRMR = 0.054; NFI > 0.90). This study bridges a notable research gap by offering region-specific insights from a semi-urban Indian context, where digital integration is on the rise but unevenly distributed. The findings have both theoretical and managerial implications, emphasizing the need for holistic transformation strategies that combine technical upskilling, cultural adaptation, and leadership engagement. The study offers practical guidance for retail managers seeking to develop a workforce that is well-prepared to adapt and thrive in a rapidly changing digital environment.