Digitalization has penetrated and transformed entire business models irrespective of industry belonging. Thus, digital transformation launches both possibilities and challenges for firms and their managers in how to execute (intra) organizational operations and strategies. This paper provides findings derived from an explorative interview study targeting required skillsets for future Engineer-to-Order (ETO) operations within the maritime industry. It has an introspective perspective, focusing on managerial perception of current and future needs to enhance efforts to digitalize ETO work further. Hence, as ETO firms tends to be conservative in their underlying dynamics of work it is important to gain insights on important skills and mindsets for successful leadership of digital transformation. The study heightens the effects of previous and future implications of digital transformation, while accentuating that new required skills are not only restricted to operators and engineers, instead it is equally relevant for managers to embrace such changing needs, as digitalization has resulted in blurred mechanisms for how to conduct management.