In an example embodiment, machine learning is utilized to automatically identify pain points of an entity. More particularly, a random forest search algorithm receives inputs from a number of different outside-in data engines. These inputs are segregated in terms of key performance indexes (KPIs), which is then fed to a random forest decision tree. The random forest search algorithm calculates a p-value for each KPI. This p-value may then be used to identify the most relevant KPIs (such as by ranking the KPIs by their respective p-values). Rules are utilized not to identify the pain points themselves, but instead to define sorting preferences (refine the ranking). Based on a combination of the p-values and the evaluation of the rules, the top-N pain points may be identified.