A system and method for automatically parsing an unstructured conversation to determine target entities for an engagement activity are provided. The method includes (i) obtaining the unstructured conversation associated with an asset using a dialogue manager, (ii) parsing the unstructured conversation using a natural language processing (NLP) model to obtain a target information associated with the asset, (iii) extracting attributes of one or more target entities from the target information using a Natural Language Understanding (NLU) model of domain of the unstructured conversation, (iv) generating, using the attributes of the one or more target entities, a definition of the cohort and at least one criteria for cohort curation for the asset by converting the unstructured conversation to a structured target information, and (v) determining a size of the one or more target entities based on the definition and the criteria for cohort curation for the asset for an engagement activity.