This open access book constitutes the refereed proceedings of the 16th International Conference on Software Business, ICSOB 2025, which took place in Stuttgart, Germany, during November 24-26, 2025. The special theme of ICSOB 2025 was Software Business in Digital Societies. The 18 full papers and 11 short papers included in the proceedings were carefully reviewed and selected from 65 submissions. They were organized in topical sections as follows: Data Economy: Data Practices, Spaces, and Architectures; Security, Trust, and Ethical Practices in Software Business; AI Adoption and Governance in Software Organizations; Sustainable and Responsible Software and Reporting; GenAI for Software Engineering and Education; Digital Strategy, Enterprise Architecture, and Value Networks; Sartups, SaaS, and Innovation Ecosystems; and Human-Centered and Socially Responsible Software Business.