Deep learning based methods are routinely used to segment various structures of interest in varied medical imaging modalities. Acquiring annotations for a large number of images requires a skilled analyst, and the process is both time consuming and challenging. Our approach to reduce effort is to reduce the number of images needing detailed annotation. For intravascular optical coherence tomography (IVOCT) image pullbacks, we tested 10% to 100% of training images derived from two schemes: equally-spaced image subsampling and deep-learning- based image clustering. The first strategy involves selecting images at equally spaced intervals from the volume, accounting for the high spatial correlation between neighboring images. In clustering, we used an autoencoder to create a deep feature space representation, performed k-medoids clustering, and then used the cluster medians for training. For coronary calcifications, a baseline U-net model was trained on all images from volumes of interest (VOIs) and compared with fewer images from the sub-sampling strategies. For a given sampling ratio, the clustering based method performed better or similar as compared to the equally spaced sampling approach (e.g., with 10% of images, mean F1 score for calcific class increased from 0.52 to 0.63, with equal spacing and with clustering, respectively). Additionally, for a fixed number of training images, sampling images from more VOIs performed better than otherwise. In conclusion, we recommend the clustering based approach to annotate a small fraction of images, creating a baseline model, which potentially can be improved further by annotating images selected using methods described in active learning research.