This chapter looks at those actors and forms of journalism that are already oriented toward the future: “pioneer journalists” and “pioneer journalism”. We first introduce pioneer journalism as a concept and unfold its theoretical foundations. Then characteristic elements of pioneer journalism as a figuration are discussed. In doing so, the actor constellations and the trans-organizational dynamics of pioneer journalism come into focus. On this basis, we reflect on different areas of experimentation as well as the role of technology and its relation to products, work practices, funding, and audience relationships. The chapter concludes by addressing the question of what we can learn from research into pioneer journalism and “innovation”. In summary, the chapter contextualizes “innovation” and the associated change in journalistic organizations within the transformation of journalism as a whole, a context through which we can grasp the conditionality of these perspectives on the field.