Digital disruptions are changing the healthcare ecosystem, requiring organizations to rethink IT strategies and develop new IT competencies. This study focuses on the exploitation and exploration tension that managers face within an IT organization of a global pharmaceutical company, and their response to the related environmental exigencies in healthcare. Dynamic capability theory (DC) provides the overall framing, while ambidexterity provides an understanding of top management’s response to the exploit–explore tensions that arise. This engaged scholarship longitudinal case study takes a shifting stories methodological approach to elicit participants’ reflections and interpretations of significant events, including their own role in evolving the ambidextrous posture of the IT organization. Through rich description stories, process related decisions have been revealed, and have provided an understanding into organizational reconfiguration of IT resources. Subsequently, this resulted in a situated grounded model for understanding DC and OA for this case. Practical insights are offered on how dynamic capability theory could be applied for IT management to be smarter at becoming more ambidextrous.