In times of turbulence in the media industry, media organizations are looking for new business models. Digitalization has led traditional news media organizations to testing new forms of advertisement, such as sponsored content and native advertising, whereas others, such as lifestyle magazines, have a longer history in collaborating with brands. Editors are key players in these developments, since they are journalist–managers and decision makers within those daily practices that shape policies and influence new product innovation and development. In this study, we examine from the editors’ point of view, how they see the process of adopting novel forms of advertisement and what ethical challenges are in the way. Building on interview data of lifestyle magazine editors and news editors in Finland (N=18), we present a study that identifies four editorial dilemmas arising from the intersection of brand collaboration and journalistic work in lifestyle magazines and provide a timely first look into an emerging new category of “hybrid editors” in newsrooms. Our results suggests that, in overall, editors’ attitudes toward new forms of brand collaboration are positive.