How do small and medium-sized enterprises (SMEs) perceive the prerequisites and critical factors of digitalization? The objective of this article is to map SMEs' digital maturity and their views on how to manage the opportunities and challenges brought about by digitalization in order to foster competitiveness in local, regional, national, and international contexts. The study draws on a resource-based perspective, which views the firm as a unique bundle of assets and resources that, if utilized in distinctive ways, can create competitive advantage. The study builds on triadic relations as an interactive learning process that occurs in the interaction between actors as the concept of open innovation postulates. This study was conducted as an interpretative phenomenological analysis (IPA) study of SMEs and actors in innovation system in Gävleborg County in Sweden. It uses a qualitative approach featuring in-depth interviews, workshops, and focus-group interviews. The findings suggest a digital divide between SMEs, with a discrepancy in opportunities to benefit from the digitalization potential among the population studied. The divide manifests itself through economics, usability, and empowerment. Digitalization should not be viewed as merely a technology issue, but as a better way to run a business, as a platform for development and dissemination of knowledge about the critical factors for increased competitiveness that creates competitive values in production with digitalization as a starting point and creates an understanding of the how and what creates competitiveness in each critical factor.