This paper identifies challenges and proposes enablers for simultaneous exploration and exploitation in Operations (the production part of a manufacturing company). It also contributes with an empirical example of organizing dual operating systems through behavioral ambidexterity during the digital transformation journey. The main challenges related to achieving simultaneous exploration and exploitation are communication, involved resources, innovation process, collaboration, and implementation. One of the proposed enablers is to develop a more supportive culture through awareness and competence development of managers about the competing cultures of exploration and exploitation. Further on, the diagnostic of opportunities model (the readiness and maturity evaluation model) is an overall enabler and can be used as a supportive dialogue tool to address several of the challenges identified. In addition to this, there also needs to be a strong focus on overall continuous communication and follow-up, especially of the proposed enablers, to support the overall change approach to reach strategic legitimacy in the organization.