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Less than truckload is an important type of road-based transportation. Based on real data and on a collaboration with industry, we show that a collaborative approach between companies offers important benefits. We propose to develop partnerships between shipping companies and to synchronize their shipments. Four operational collaborative schemes with different objectives are developed. The first one focuses on minimizing shipping costs for shippers. The second and third ones minimize the carrier’s costs and the environmental cost, respectively. The fourth one is a combination of all three. The results of our computational experiments demonstrate that collaboration lead to significant cost reductions.