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Technology acceptance is increasingly gaining attention in research considering the continuous exploits of innovation and various derived advantages. Cloud computing (CC) has shown to be the ideal solution for aligning information technology with business strategies. However, small to medium-sized enterprises (SMEs) in the payment card industry are reluctantly adopting this technology despite the benefits. This correlational study aims at investigating whether security, cost effectiveness, or regulatory compliance influence CC adoption by U.S. SMEs in the payment card sector. The study builds on the technology-organization-environment (TOE) framework and uses a previously validated instrument to assess CC adoption by decision-makers in U.S. SMEs handling payment data. A multiple linear regression analysis of survey data from 140 participants indicated that the model could predict CC acceptance. Cost effectiveness and regulatory compliance significantly predicted the decision to adopt CC with a strong and positive effect. Pearson’s coefficients indicated a significant correlation between each independent variable and the outcome variable. Leaders in small payment markets may gain the latest insights on cloud services in their technology decisions. Cloud service providers may be well informed on consumers’ demands for the effective delivery of products and services. Implications for positive social change include enhanced cloud security to reduce compliance defects, cybersecurity attacks, and small business failures. This study may increase consumers’ confidence and comfort while using their credit or debit cards in various sales outlets, thus boosting business performance and employment with a better quality of life.