Impact measurement is crucial for sustainable ventures to assess the extent to which they bring about sustainable development. Moving beyond impact measurement as a static activity, we develop a prospective multiple case process study to explore how impact measuring unfolds over time. From our analysis emerges that sustainable ventures move along three trajectories?reactive, proactive, and agentic impact measuring?which produce distinct positions of impact in the sustainable venture’s value proposition as a result. Thus, we propose a novel process perspective on impact measuring, unveiling the role of agency along different impact measuring trajectories and uncover the relationship between impact measurement and the value proposition in sustainable business models.