Techniques described herein implement heading identification and classification for a digital document in a digital medium environment. A document analysis system is leveraged to extract structural features from a digital document, identify heading candidates from among the structural features, validate the headings candidates, and classify validated headings into different headings types. The classified headings are then utilized to generate a sectioned version of the digital document (“sectioned document”) that is divided into different sections based on the headings. Further, a document directory is generated that includes the headings and that enables navigation to different sections of the sectioned document.