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Looking at this seriously for a moment, the best time to ult with kayo is when you believe People are about to react, such as when it's post plant, or maybe if you want to deal with an annoying Cypher, whom you can usually disable his trips with your ult and run site, etc etc, you need to find a reason to reveal yourself every pulse and find a reason that is worth it for your team
So NOT specifically when you entry, because people can very easily give up for a short while and try again later, this is where game sense really is the best thing for you