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In the wake of the changing perception of corporate social responsibility and of the blurring of responsibilities between state, businesses and nonprofits a shift in sector roles seems to be taking place. Cross-sector partnerships are innovative solutions for fostering economic and social development and play a seminal role in the quest for sustainable development, since societal challenges are getting too complex and too interdependent to be solved via single sector solutions. On the path towards sustainability there are still many challenges for businesses and nonprofits. Even if corporate philanthropy has evolved in the last decades it still lacks a strategic focus and Corporate Social Responsibility (CSR) initiatives are not embedded in the existing company processes and strategy yet. Both sectors need to develop more professional approaches for the definition, management and implementation of their cross-sector alliances. Furthermore the Third Sector is getting under pressure to increase the transparency of its activities and enhance staff and resources efficiency. The paper is offering some viable solutions to meet these challenges: a set of guidelines for businesses and nonprofits in order to succeed in their strategic alliances; the analysis of Venture Philanthropy as an innovative collaboration approach that applies venture capital methods to cross-sector partnerships in order to maximize the social impact of nonprofits’ resources; the ‘Trust Capital Model’ as a tool to manage businesses’ CSR programs and to define the bundle of initiatives which contribute most to sustainability and to the company’s bottom-line. Moreover, through the attempt to categorize partnerships into a typology the paper offers a framework for identifying alliances that can have a greater impact in solving social and environmental issues and which have the potential to create high social and market value.