Find the moments that precede a good upgrade
Look at accounts that did upgrade and ask what they had just done. Candidate moments include a sent proposal, a repeat use, or a teammate joining. Treat these as hypotheses; confirm them in interviews before building a trigger around them.
Separate “limit reached” from “value received”
Segment people who hit the limit after completing something useful from those who hit it while still trying to finish their first result. They likely need different messages, and only the first group may be ready to hear about pricing.
Be careful with small groups. A handful of accounts cannot support a confident conclusion.
Offer the ask where it can be answered
A calm comparison of plans after a completed result gives the customer something to weigh. Include what stays free, so the choice does not feel like a threat, and make it easy to dismiss without penalty.
What remains unknown
No real upgrade data, baseline, or conversion change has been measured here. The proposed prompt is a hypothesis to test.
