Social media constitute an important arena for public debates and steady interchange of issues relevant to society. To boost their reputation, commercial organizations also engage in political, social, or environmental debates on social media. To engage in this type of digital activism, organizations increasingly utilize the social media profiles of executive employees and other brand ambassadors. However, the relationship between brand ambassadors’ digital activism and corporate reputation is only vaguely understood. The results of a qualitative inquiry suggest that digital activism via brand ambassadors can be risky (e.g., creating additional surface for firestorms, financial loss) and rewarding (e.g., emitting authenticity, employing ‘megaphones’ for industry change) at the same time. The paper informs both scholarship and practitioners about strategic trade-offs that need to be considered when employing brand ambassadors for digital activism.