What is the best way to set up a Win/Loss Analysis for users that subscribe or don't subscribe after a free trial?

Our company is working to do a win/loss analysis of what types of behaviors/features do users use in our application that end up subscribing vs. what they do for users that end up not subscribing at the end of a trial so that we can drive more users to the features that will hopefully get them to subscribe. I know we have some good metrics we can use in Pendo for this such as looking at user paths, retention by first user, etc. However, we are having trouble creating the best segments to use for these. Since when the user subscribes they are marked as either "is paying =true and in trail = false" OR "is paying = false and in trail = true" we are having trouble drilling down to the currently subscribed users finding what they did within the system when they WEREN'T subscribed/paying. Also customers that didn't subscribe trying to map back to when they were in a trial and drilling down just to those users. If you have any thoughts/advice on segmenting please let me know! Thanks!