Business associativity is consolidated as a decisive strategy to enhance competitiveness, sustainability, and organizational growth in regional contexts. This study analyzed the dynamics of associativity in companies in the city of Ibagué (Colombia), with the purpose of identifying the determining factors that condition its adoption from the perspective of strategic management. A mixed-method methodology was employed, combining qualitative and quantitative techniques supported by descriptive statistics, cross-tabulation, and correlation analysis. The results show that activities related to agricultural production and input marketing exhibit the highest levels of associativity and inter-company cooperation. In contrast, a significant lag was identified in the incorporation of digital technologies, especially in rural areas, where connectivity limitations represent a structural barrier to associative integration. Likewise, it was observed that most respondents (n = 134) do not participate in formal association schemes, although they show a high willingness to join collaborative processes. The findings suggest that associativity in Ibagué faces challenges related to technological gaps and connectivity barriers but offers significant potential to boost regional competitiveness through the strengthening of business networks and the generation of productive synergies. This study provides empirical evidence that contributes to the design of public policies and management strategies aimed at consolidating resilient and innovative business ecosystems.