A number of applications and algorithms have emerged over the past few years claiming to calculate the personal influence of a user across different social network sites, namely the capacity to engage with other users in online conversations and actions. The most established of these applications is Klout (https://klout.com), a privately owned online service that browses and scrapes the activity of individual profiles across the most important social media platforms to create an individual “influence score.” Sites like Klout market their supposed ability to assess the user’s capacity to influence the online behavior of others, especially in terms of sharing content and generating interactions. The rapid diffusion of such services has helped popularize the term influencer as a status indicating the online reputation of a user on a certain topic across a network of personal contacts, in a way that recalls the notion of opinion leadership. The present contribution discusses Klout’s effectiveness at measuring influence and reputation across creative environments and networks. Does Klout really measure influence and, as a consequence, the reputation of a user across a network of contacts? Is the online influence on Klout a potential proxy for the “general” reputation of a creative professional in a network? This study will use data coming from research on freelance creatives and their professional networks in Milan and London, focusing on the extent of personal reputations within the networks. The research shows that reputation is a determinant element for the professional success of freelance creatives in these networks, as it appears to be more relevant than other factors, such as trust, skills, and the educational titles.