In the manuscript, the issue of detecting and segmenting out pavement defects on highway roads is addressed. Specifically, computer vision (CV) methods are developed and applied to the problem based on deep learning of convolutional neural networks (ConvNets). A novel neural network structure is considered, based on a pipeline of three ConvNets and endowed with the capacity for context awareness, which improves grid-based search for defects on orthoframes by considering the surrounding image content—an approach, which essentially draws inspiration from how humans tend to solve the task of image segmentation. Also, methods for assessing the quality of segmentation are discussed. The contribution also describes the complete procedure of working with pavement defects in an industrial setting, involving the workcycle of defect annotation, ConvNet training and validation. The results of ConvNet evaluation provided in the paper hint at a successful implementation of the proposed technique.