Users don't upgrade even though they love the product
Don't put upgrade buttons in the sidebar. Show them the exact moment users try to do something they can't on their current plan.
When to use
You have a freemium product with clear feature differences between plans.
Hypothesis template
If we show upgrade prompts at the moment users hit fill in: feature limit, conversion will increase by fill in: target% because motivation is highest when they need the feature.
Method
The problem: Your upgrade button sits in the settings page. Users who'd benefit from Pro never see it at the right time.
What works: Show the upgrade prompt at the exact moment users try to do something beyond their plan. Not a generic banner — a contextual message at the point of friction.
The result: Contextual upgrade prompts convert 3-5x higher than settings-page upgrade buttons because the user is motivated right now.
How to do it:
- List every feature or limit that differs between plans
- For each one, design a prompt that appears when free users try to use it
- Show what they'd get: "Upgrade to Pro to create unlimited experiments"
- Include a one-click upgrade or free trial start
- Let them dismiss without friction — don't block them
- Track which upgrade prompts convert best and optimize those
Key insight: The best time to sell is when the user is trying to do the thing you're selling. Not before, not after.
Success metrics
- •Contextual prompt conversion rate
- •Upgrade rate by trigger point
- •Revenue from contextual upsells
- •Dismiss rate (should be reasonable)
Prerequisites
- Feature-level analytics to know when users hit limits
- A way to show inline upgrade prompts
- A fast upgrade flow (ideally one-click)
Common pitfalls
- •Showing prompts too aggressively (every action)
- •Blocking users instead of suggesting
- •Not making it easy to dismiss
- •Having a slow checkout flow after the prompt
Source: Canva, Notion, Figma. Contextual upgrade prompts convert 3-5x higher than settings-page buttons.
Suggested ICE scores
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