A new type of worker, the gig worker, is acknowledge and problematized as to what challenges mediators can face with managing them as previous research points out their differences from other workers. The purpose of this study was to identify and analyze challenges that a mediator can face when managing gig workers and also elevate the knowledge regarding gig workers on how to work with them. A semi-structured interview was conducted with four participants, three mediators of established gig firms in Sweden and one management consultant and expert in the field of gig economy. The finding indicated that there exist two challenges that mediators can face when managing gig workers: 1) The expectations of the matchmaking 2) Allowing gig workers to be independent