Winckler studied film at the HfG Offenbach and the HfBK Hamburg. He has taught at various film schools, including the DFFB, Film University Babelsberg, and MetFilm School Berlin. Before directing his own feature films, he worked as a camera assistant, screenwriter, and script consultant, and made several short films.
His feature-length films Klassenfahrt and Lucy were screened at festivals such as the Berlinale, the London Film Festival, and Karlovy Vary, where they received multiple awards. Together with Ulrich Köhler, he co-wrote and co-directed Das freiwillige Jahr, which was shown in the international competition at the Locarno Film Festival and also received the German Film Critics’ Award for Best Screenplay.