Does business success in uncertain times depend on company’s ability to achieve a “twin transformation,” through discovery of new values at the crossroads of digital technology and sustainability to bolster competitiveness? The objective of this chapter is to examine value generation at the intersection of digital transformation and sustainable strategies, particularly through decision-support tools enabling unified data access across organisational boundaries. Theoretical underpinning/Methodology: Grounded in resource-based view, socio-technical theory, and dynamic capability perspective, this qualitative study collects data from enterprises of varying sizes, including 300 cluster organization members. Findings: Companies adept at integrating digital and sustainable strategies—“Twin Transformers”—are more likely to succeed. Despite Sweden’s strong focus on sustainability, few companies actively pursue this transformative path. Conclusions/Implications: Companies need to broaden their perspective to fully embrace twin transformation. Originality: This study highlights the integration of digital and sustainable practices as essential for future competitiveness, addressing a gap in the current literature.