In the ongoing discussion of how companies make a difference to society, various corporate–community transactions have been observed and advocated. This chapter explores the multiple forms of philanthropic transactions including gifts, strategic philanthropy, sponsorship, shared value and social entrepreneurship. We categorize these as either gifts, expenditures or more operational investments. We then examine the reach of their impact, considering responsible global leadership, as well as the macro (organization’s interaction with society), meso (organization itself) and micro (individual manager) levels. We find that this analysis leads to four themes which elaborate on these transactions, including a range of give and take, various levels of purposeful involvement, emphasis on outcomes and vulnerable compassion being present at the individual leader level. Our research suggests leaders must question their own motivations and expectations as diligently as they typically do those of their counterparty. We propose that responsible global leaders, with their ability to manage complexity, respond to diversity and hold compassion are likely to be able to navigate this terrain, to engage in projects and programs that contribute to business needs, while at the same time making a positive difference to the communities in which they operate. We conclude with implications of findings for corporate leaders, practitioners and academics.