An automated content labeling system is disclosed. An example embodiment is configured to: register a plurality of labelers to which annotation tasks are assigned; populate a labeling queue with content data to be annotated; assign annotation tasks from the labeling queue to the plurality of labelers; and provide a superpixel annotation tool enabling the plurality of labelers to configure a size of a segment cluster in an image of the content data, and select each segment cluster to be included in a segmentation feature with a specified object class, the segment clusters including similarly colored pixels from the image.