HoloTracker enables schools to show evidence of deep skills and character growth by capturing, analysing and communicating observational data. Today, there is a growing impetus to support holistic learning. Worldwide, schools are experiencing a monumental turn to embrace non-academic success as a norm, and to nurture students who take ownership over their role in society beyond individual success. Yet limited progress has been made in learning institutions. A central reason is that educators lack the means to assess and track students’ whole-person learning progress. HoloTracker supports learning institutions in augmenting their assessment processes to effectively articulate whole-person development. This holistic approach is achieved through a simple and multi-dimensional formative assessment process. Through an easy and intuitive webapp, teachers and students are empowered to collect powerful observational data about day-to-day learning. Leveraging AI, these observational trends are translated into impactful visualisations and natural language draft reports depicting individual or group ¬¬learning patterns in real-time. HoloTracker currently supports 20+ schools in Singapore, with further pilots across Asia and Latin America.