A clustering model is used to partition a set of historical opportunity profiles representing historical opportunities into a plurality of opportunity profile clusters. A target opportunity profile that includes a plurality of target-opportunity parameters is obtained, and an opportunity profile cluster is identified that meets a matching criterion with the target opportunity profile. The plurality of historical opportunity profiles of the identified opportunity profile cluster are partitioned based on an outcome indicator associated respectively with each of the plurality of historical opportunity profiles, providing a first subset of historical opportunity profiles and a second subset of historical opportunity profiles. An insight generation model is applied to the target opportunity profile along with the first subset and/or the second subset to generate one or more insights for the target opportunity profile.