This study explores schools' digital maturity self-evaluation reports' data from Estonia. Based on quantitative data (N = 499) the schools that attempt digital transformation were clustered into three successive digital improvement types. The paper describes 3 main patterns of school improvement in different phases of innovative change: classroom innovation practices' driven schools, participatory led structural change driven schools; and inclusive and evidence based change management type of schools. The defining variables for digital transformation towards new levels of digital maturity were teachers' role, digital competences, learning organization culture, participatory management, inclusive leadership, structural changes and network, and IT-manager involvement to structural changes.