ClickUp’s upsell emails are triggered by usage limits and framed around immediate value. They highlight what features the user is missing out on, show real examples of the limitation (like Activity View cutoffs), and present a clear, benefit-driven upgrade offer. The messaging stays positive and opportunity-focused, with strong CTAs to upgrade and easy access to compare plans. The tone is helpful, not pushy — designed to feel like an invitation to unlock more potential rather than a hard sell.
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