Information systems (IS) have been introduced in enterprises for decades to generate business value. Historically systems that are deeply integrated into business processes and not replaced remain vital assets, and thus become legacy IS (LISs). To secure the future success, enterprises invest in innovative technologies such as artificial intelligence-based services (AIBSs), enriching LISs and assisting employees in the execution of work-related tasks. This study develops design requirements from a managerial perspective by following a mixed-method approach. First, we conducted ten interviews to formulate requirements to design AIBSs. Second, we evaluated their business value using an online survey (N = 101). The results indicate that executives consider design requirements as relevant that create strategic advancements in the short term. With the help of our findings, researchers can better understand where further in-depth studies are needed to refine the requirements. Practitioners can learn how AIBSs generate business value when enriching LISs.