Little is known about how digital work shapes the exchange of performance feedback, even though today’s digital and global world demands for more continuous feedback than annual reviews. This research investigates a feedback app in a naturalistic context within a globally leading financial service corporation (InsurCorp). Drawing on malleability and voluntary participation, the app offers possibilities to send and request feedback between employees. Rich contextual insights from a multinational pilot study with 568 users are gained by triangulating qualitative data from 21 semi-structured interviews and 69 feedback app user reviews with usage data. Anchored in the theory of affordances, we provide insights on use practices and find that the app affords operational-level feedback exchange on specific subjects, while general feedback on sensitive topics is preferably exchanged in person. To understand actualization facilitators and barriers, we take a social-technical systems perspective to elaborate contextual factors that influence the individual’s actualization decision.