Thanks @karstenkoehler and @danmoyle - really great solutions both of them. However, I don’t think our data at this point is ready to support them entirely. But, I will dig in to both to see how far I can get!
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On a sidenote: It’s one of the blockers for what I consider Hubspot being fully ready for the Customer Success use case. I have worked with 6 different Customer Success tools, and all can do this in 2-3 clicks. (Planhat for example has a simple trigger: if this property value has increased with 10% over the past 7 days, then send notification)