Web Science is an interdisciplinary field dedicated to understanding the complex and multiple impacts of the Web on society and vice versa. The discipline is well situated to address pressing issues of our time by incorporating various scientific approachs, including the interplay between the Web, AI and society. New advances in AI are revolutionizing the way in which people use the Web and interact through it. As these technologies develop, it is crucial to examine their effect on society and the socio-technical environment in which we find ourselves. We are nearing the crossroads wherein content on the Web will increasingly be automatically generated, blended with that created by humans. This creates new potential yet brings new challenges and exacerbates existing ones in relation to data quality and misinformation. Additionally, we need to consider the role of the Web as a source of data for AI, including privacy and copyright concerns, as well as bias and representativity of resulting systems. The potential impact of new AI tools on the nature of work may bring a transformation of some careers while creating whole new ones.