Abstract: Technologies are provided for generation of points of insertion of directed content into a video asset. In some embodiments, multiple time offsets within an interval spanned by the video asset can be determined using audio data corresponding to the video asset. A time offset defines a boundary between first and second segments of the video asset. Using image data corresponding to the video asset, respective pairs of video clips for the multiple time offsets can be generated. Visual features, aural features, and language features pertaining to the respective pairs of video clips can then be generated. Scores for the multiple time offsets can be generated using the visual features, the aural features, and the language features. A score represents an assessment of suitability to insert directed content into the video asset at a time offset. A file that contains specific time offsets can be generated.