Although information technology has become advanced in profiling users, we often offer this knowledge to marketing and forget that profiling is needed for information technology implementation itself. If digitalization is introduced in a firm, it may encounter internal resistance. Top managers, middle managers, and front-line employees may have different expectations with regard to digitalization initiatives in their firms. Having different visions of what digitalization is about may result in conflicts with regard to digital solutions selection and implementation and, consequently, lead to digitalization failure. In this paper, we look at differences in digitalization cost perception using a Discrete Choice Experiment. Based on our findings, we propose to approach firms by profiling top managers, middle managers, and front-line employees.