Upgrade prompts feel random and annoying

The problem: Pop-up says "Upgrade to Pro!" User thinks: "Why? I don't need Pro." They close it. You've trained them to ignore upgrade prompts.

The fix: Show upgrade prompts at the moment of constraint. When they try to
add a 6th team member on a 5-user plan. When they hit the storage limit. When they try to use a gated feature.

Why context matters:

• The pain is real and immediate
• Value proposition is obvious
• User is already doing the thing that needs upgrade
• Not interruptive, it's informative
• "Oh, that's why I'd upgrade" vs "stop showing me this"

Good timing:

• Attempting to exceed user/storage/usage limits
• Clicking a premium feature
• After completing onboarding (they know the product now)
• When usage patterns suggest they'd benefit

Bad timing:

• Random pop-ups
• During first session
• Middle of a workflow
• Right after signup

How to do it:

1. Map all free tier limits
2. Build upgrade prompts for each limit point
3. Explain what they get, not just "upgrade now"
4. A/B test contextual vs non-contextual prompts
5. Track which contexts convert best