Digital transformation has become a critical driver of competitiveness for small and medium-sized enterprises (SMEs), yet its strategic application in resource-constrained contexts remains underexplored. This study examined the effect of mobile money transfer and cloud computing on strategic decision-making among small and medium business start-ups (SMBSUs) in Kisumu County, Kenya. A sequential explanatory mixedmethods design was adopted, combining a quantitative survey of 199 founders and senior managers across sectors such as retail, agribusiness, services, and manufacturing with qualitative interviews involving 12–15 purposively selected respondents. Quantitative data were analyzed using descriptive statistics, chi-square tests, correlation, and multiple regression in SPSS, while qualitative data were subjected to thematic analysis using NVivo. Findings revealed that mobile money was the most widely adopted tool though it primarily served operational purposes with negligible strategic impact. Conversely, cloud computing showed limited strategic contribution due to infrastructural and skill-related barriers. The study highlights the uneven integration of digital tools into strategic processes and identifies leadership capacity, infrastructure, and cost as key determinants of adoption. These insights inform policy and practice by emphasizing the need for targeted interventions to strengthen digital literacy, improve access to affordable technologies, and foster inclusive digital ecosystems in devolved regions.