Forecasting and decision-making are generally modeled as two sequential steps with no feedback, following an open-loop approach. In this paper, we present application-driven learning, a new closed-loop framework in which the processes of forecasting and decision-making are merged and co-optimized through a bilevel optimization problem. We present our methodology in a general format and prove that the solution converges to the best estimator in terms of the expected cost of the selected application. Then, we propose two solution methods: an exact method based on the KKT conditions of the second-level problem and a scalable heuristic approach suitable for decomposition methods. The proposed methodology is applied to the relevant problem of defining dynamic reserve requirements and conditional load forecasts, offering an alternative approach to current \emph{ad hoc} procedures implemented in industry practices. We benchmark our methodology with the standard sequential least-squares forecast and dispatch planning process. We apply the proposed methodology to an illustrative system and to a wide range of instances, from dozens of buses to large-scale realistic systems with thousands of buses. Our results show that the proposed methodology is scalable and yields consistently better performance than the standard open-loop approach.