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In this paper, we investigate the use of deep learning for solving a classical NP-Hard single machine scheduling problem where the criterion is to minimize the total tardiness. Instead of designing an end-to-end machine learning model, we utilize well known decomposition of the problem and we enhance it with a data-driven approach. We have designed a regressor containing a deep neural network that learns and predicts the criterion of a given set of jobs. The network acts as a polynomial-time estimator of the criterion that is used in a single-pass scheduling algorithm based on Lawler's decomposition theorem. Essentially, the regressor guides the algorithm to select the best position for each job. The experimental results show that our data-driven approach can efficiently generalize information from the training phase to significantly larger instances (up to 350 jobs) where it achieves an optimality gap of about 0.5%, which is four times less than the gap of the state-of-the-art NBR heuristic.