Over 25 million Small and Medium Enterprises (SMEs) in Europe face multiple challenges related to personal data protection (PDP), ranging from awareness of EU’s General Data Protection Regulation (GDPR) to a clear and practical roadmap to compliance. Many also cannot afford access to enterprise-grade cybersecurity technology. This paper presents the main objectives and innovations of the EU-funded SENTINEL project, which introduces the concept of Intelligence for Compliance; it integrates tried-and-tested modular cybersecurity and privacy technologies with fresh, ambitious ones, such as a novel Identity Management System (IdMS) for human-centric data portability, and an end-to-end PDP compliance self-assessment framework. Combined with machine learning powered recommendations, policy drafting and enforcement for compliance, and a set of plugins that contains cybersecurity, data privacy and simulations/training software tools, SENTINEL aims to help small enterprises feel considerably more secure by safeguarding their and their customers’ assets.