This study investigated the influence of digital orientation on the digital transformation of Multi-Purpose Cooperatives in Davao Region, Philippines. Digital transformation, characterized by the integration of new technologies and systems into an organization’s strategic processes, is the focal point of the study which utilizes an explanatory sequential mixed methods design. Quantitative data, sourced from 316 respondents employing stratified random sampling with proportional technique, reveals that MPCs of all sizes exhibit high levels of digital orientation and digital transformation. This showcases a readiness to embrace new technologies and engage in digitalization initiatives among MPCs. Notably, smaller MPCs demonstrate significantly higher digital orientation compared to medium-sized ones, potentially due to their agility and openness to new trends. Intriguingly, having a digital orientation proved to be a significant predictor of successful digital transformation for medium and large MPCs, whereas, this relationship is not significant for smaller cooperatives. Qualitative data reinforced and enriched these findings, emphasizing the challenges faced by smaller MPCs in terms of resources and technology access. Furthermore, diverse perspectives on the relationship between digital orientation and transformation for smaller cooperatives, highlight the need for further investigation into unique factors influencing their digital journeys. Ultimately, this study reveals a detailed examination of MPCs in Davao Region as they navigate the digital world, emphasizing their collective effort to digitalization while highlighting differences in approaches between larger and smaller cooperatives. Understanding these various aspects opens the door to creating tailored support to help all MPCs—big or small—on their digital transformation journeys.