“Another really critical part of this strategy is like the who and when — so who are the cohorts that you're targeting and being really thoughtful around the specific cohorts... and then the when and the context — did they recently interact with a particular feature, how long have they been with the product.”

Target Upsells by 'Who and When' — Cohort Plus Context Together Drive Conversion

Effective upsells require two inputs working together: the right audience cohort (who has shown signals of value, engagement, or need) and the right contextual moment (recently touched a gated feature, approaching a usage limit). Either alone produces mediocre results; combining them creates upsells that feel helpful rather than intrusive.