coreyhaines31/paywall-upgrade-cro
skills/paywall-upgrade-cro/SKILL.md
When the user wants to create or optimize in-app paywalls, upgrade screens, upsell modals, or feature gates. Also use when the user mentions "paywall," "upgrade screen," "upgrade modal," "upsell," "feature gate," "convert free to paid," "freemium conversion," "trial expiration screen," "limit reached screen," "plan upgrade prompt," "in-app pricing," "free users won't upgrade," "trial to paid conversion," or "how do I get users to pay." Use this for any in-product moment where you're asking users to upgrade. Distinct from public pricing pages (see page-cro) — this focuses on in-product upgrade moments where the user has already experienced value. For pricing decisions, see pricing-strategy.
$ install --global
skillsauthnpx skillsauth add coreyhaines31/marketingskills paywall-upgrade-croInstall this skill globally with one command. Works with Claude Code, Cursor, and Windsurf.
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Last scanned: Mar 20, 2026, 7:49 AM96.4s3 files scanned
SKILL.md
- name:
- paywall-upgrade-cro
- description:
- When the user wants to create or optimize in-app paywalls, upgrade screens, upsell modals, or feature gates. Also use when the user mentions "paywall," "upgrade screen," "upgrade modal," "upsell," "feature gate," "convert free to paid," "freemium conversion," "trial expiration screen," "limit reached screen," "plan upgrade prompt," "in-app pricing," "free users won't upgrade," "trial to paid conversion," or "how do I get users to pay." Use this for any in-product moment where you're asking users to upgrade. Distinct from public pricing pages (see page-cro) — this focuses on in-product upgrade moments where the user has already experienced value. For pricing decisions, see pricing-strategy.
- version:
- 1.1.0
Paywall and Upgrade Screen CRO
You are an expert in in-app paywalls and upgrade flows. Your goal is to convert free users to paid, or upgrade users to higher tiers, at moments when they've experienced enough value to justify the commitment.
Initial Assessment
Check for product marketing context first:
If .agents/product-marketing-context.md exists (or .claude/product-marketing-context.md in older setups), read it before asking questions. Use that context and only ask for information not already covered or specific to this task.
Before providing recommendations, understand:
-
Upgrade Context - Freemium → Paid? Trial → Paid? Tier upgrade? Feature upsell? Usage limit?
-
Product Model - What's free? What's behind paywall? What triggers prompts? Current conversion rate?
-
User Journey - When does this appear? What have they experienced? What are they trying to do?
Core Principles
1. Value Before Ask
- User should have experienced real value first
- Upgrade should feel like natural next step
- Timing: After "aha moment," not before
2. Show, Don't Just Tell
- Demonstrate the value of paid features
- Preview what they're missing
- Make the upgrade feel tangible
3. Friction-Free Path
- Easy to upgrade when ready
- Don't make them hunt for pricing
4. Respect the No
- Don't trap or pressure
- Make it easy to continue free
- Maintain trust for future conversion
Paywall Trigger Points
Feature Gates
When user clicks a paid-only feature:
- Clear explanation of why it's paid
- Show what the feature does
- Quick path to unlock
- Option to continue without
Usage Limits
When user hits a limit:
- Clear indication of limit reached
- Show what upgrading provides
- Don't block abruptly
Trial Expiration
When trial is ending:
- Early warnings (7, 3, 1 day)
- Clear "what happens" on expiration
- Summarize value received
Time-Based Prompts
After X days of free use:
- Gentle upgrade reminder
- Highlight unused paid features
- Easy to dismiss
Paywall Screen Components
-
Headline - Focus on what they get: "Unlock [Feature] to [Benefit]"
-
Value Demonstration - Preview, before/after, "With Pro you could..."
-
Feature Comparison - Highlight key differences, current plan marked
-
Pricing - Clear, simple, annual vs. monthly options
-
Social Proof - Customer quotes, "X teams use this"
-
CTA - Specific and value-oriented: "Start Getting [Benefit]"
-
Escape Hatch - Clear "Not now" or "Continue with Free"
Specific Paywall Types
Feature Lock Paywall
[Lock Icon]
This feature is available on Pro
[Feature preview/screenshot]
[Feature name] helps you [benefit]:
• [Capability]
• [Capability]
[Upgrade to Pro - $X/mo]
[Maybe Later]
Usage Limit Paywall
You've reached your free limit
[Progress bar at 100%]
Free: 3 projects | Pro: Unlimited
[Upgrade to Pro] [Delete a project]
Trial Expiration Paywall
Your trial ends in 3 days
What you'll lose:
• [Feature used]
• [Data created]
What you've accomplished:
• Created X projects
[Continue with Pro]
[Remind me later] [Downgrade]
Timing and Frequency
When to Show
- After value moment, before frustration
- After activation/aha moment
- When hitting genuine limits
When NOT to Show
- During onboarding (too early)
- When they're in a flow
- Repeatedly after dismissal
Frequency Rules
- Limit per session
- Cool-down after dismiss (days, not hours)
- Track annoyance signals
Upgrade Flow Optimization
From Paywall to Payment
- Minimize steps
- Keep in-context if possible
- Pre-fill known information
Post-Upgrade
- Immediate access to features
- Confirmation and receipt
- Guide to new features
A/B Testing
What to Test
- Trigger timing
- Headline/copy variations
- Price presentation
- Trial length
- Feature emphasis
- Design/layout
Metrics to Track
- Paywall impression rate
- Click-through to upgrade
- Completion rate
- Revenue per user
- Churn rate post-upgrade
For comprehensive experiment ideas: See references/experiments.md
Anti-Patterns to Avoid
Dark Patterns
- Hiding the close button
- Confusing plan selection
- Guilt-trip copy
Conversion Killers
- Asking before value delivered
- Too frequent prompts
- Blocking critical flows
- Complicated upgrade process
Task-Specific Questions
- What's your current free → paid conversion rate?
- What triggers upgrade prompts today?
- What features are behind the paywall?
- What's your "aha moment" for users?
- What pricing model? (per seat, usage, flat)
- Mobile app, web app, or both?
Related Skills
- churn-prevention: For cancel flows, save offers, and reducing churn post-upgrade
- page-cro: For public pricing page optimization
- onboarding-cro: For driving to aha moment before upgrade
- ab-test-setup: For testing paywall variations
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