Although Deep Learning is the new gold standard in medical image segmentation, the annotation burden limits its expansion to clinical practice. We also observe a mismatch between annotations required by deep learning methods designed with pixel-wise optimization in mind and clinically relevant annotations designed for biomarkers extraction (diameters, counts, etc.). Our study proposes a first step toward bridging this gap, optimizing vessel segmentation based on its diameter annotations. To do so we propose to extract boundary points from a star-shaped segmentation in a differentiable manner. This differentiable extraction allows reducing annotation burden as instead of the pixel-wise segmentation only the two annotated points required for diameter measurement are used for training the model. Our experiments show that training based on diameter is efficient; produces state-of-the-art weakly supervised segmentation; and performs reasonably compared to full supervision.