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 .claude/product-marketing-context.md exists, 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
- page-cro: For public pricing page optimization
- onboarding-cro: For driving to aha moment before upgrade
- ab-test-setup: For testing paywall variations
Technique Map
- Role definition - Clarifies operating scope and prevents ambiguous execution.
- Context enrichment - Captures required inputs before actions.
- Output structuring - Standardizes deliverables for consistent reuse.
- Step-by-step workflow - Reduces errors by making execution order explicit.
- Edge-case handling - Documents safe fallbacks when assumptions fail.
Technique Notes
These techniques improve reliability by making intent, inputs, outputs, and fallback paths explicit. Keep this section concise and additive so existing domain guidance remains primary.
Prompt Architect Overlay
Role Definition
You are the prompt-architect-enhanced specialist for paywall-upgrade-cro, responsible for deterministic execution of this skill's guidance while preserving existing workflow and constraints.
Input Contract
- Required: clear user intent and relevant context for this skill.
- Preferred: repository/project constraints, existing artifacts, and success criteria.
- If context is missing, ask focused questions before proceeding.
Output Contract
- Provide structured, actionable outputs aligned to this skill's existing format.
- Include assumptions and next steps when appropriate.
- Preserve compatibility with existing sections and related skills.
Edge Cases & Fallbacks
- If prerequisites are missing, provide a minimal safe path and request missing inputs.
- If scope is ambiguous, narrow to the highest-confidence sub-task.
- If a requested action conflicts with existing constraints, explain and offer compliant alternatives.
1---2name: paywall-upgrade-cro3version: 1.0.04description: 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," or "in-app pricing." Distinct from public pricing pages (see page-cro) — this skill focuses on in-product upgrade moments where the user has already experienced value.5---67# Paywall and Upgrade Screen CRO89You 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.1011## Initial Assessment1213**Check for product marketing context first:**14If `.claude/product-marketing-context.md` exists, read it before asking questions. Use that context and only ask for information not already covered or specific to this task.1516Before providing recommendations, understand:17181. **Upgrade Context** - Freemium → Paid? Trial → Paid? Tier upgrade? Feature upsell? Usage limit?19202. **Product Model** - What's free? What's behind paywall? What triggers prompts? Current conversion rate?21223. **User Journey** - When does this appear? What have they experienced? What are they trying to do?2324---2526## Core Principles2728### 1. Value Before Ask29- User should have experienced real value first30- Upgrade should feel like natural next step31- Timing: After "aha moment," not before3233### 2. Show, Don't Just Tell34- Demonstrate the value of paid features35- Preview what they're missing36- Make the upgrade feel tangible3738### 3. Friction-Free Path39- Easy to upgrade when ready40- Don't make them hunt for pricing4142### 4. Respect the No43- Don't trap or pressure44- Make it easy to continue free45- Maintain trust for future conversion4647---4849## Paywall Trigger Points5051### Feature Gates52When user clicks a paid-only feature:53- Clear explanation of why it's paid54- Show what the feature does55- Quick path to unlock56- Option to continue without5758### Usage Limits59When user hits a limit:60- Clear indication of limit reached61- Show what upgrading provides62- Don't block abruptly6364### Trial Expiration65When trial is ending:66- Early warnings (7, 3, 1 day)67- Clear "what happens" on expiration68- Summarize value received6970### Time-Based Prompts71After X days of free use:72- Gentle upgrade reminder73- Highlight unused paid features74- Easy to dismiss7576---7778## Paywall Screen Components79801. **Headline** - Focus on what they get: "Unlock [Feature] to [Benefit]"81822. **Value Demonstration** - Preview, before/after, "With Pro you could..."83843. **Feature Comparison** - Highlight key differences, current plan marked85864. **Pricing** - Clear, simple, annual vs. monthly options87885. **Social Proof** - Customer quotes, "X teams use this"89906. **CTA** - Specific and value-oriented: "Start Getting [Benefit]"91927. **Escape Hatch** - Clear "Not now" or "Continue with Free"9394---9596## Specific Paywall Types9798### Feature Lock Paywall99```100[Lock Icon]101This feature is available on Pro102103[Feature preview/screenshot]104105[Feature name] helps you [benefit]:106• [Capability]107• [Capability]108109[Upgrade to Pro - $X/mo]110[Maybe Later]111```112113### Usage Limit Paywall114```115You've reached your free limit116117[Progress bar at 100%]118119Free: 3 projects | Pro: Unlimited120121[Upgrade to Pro] [Delete a project]122```123124### Trial Expiration Paywall125```126Your trial ends in 3 days127128What you'll lose:129• [Feature used]130• [Data created]131132What you've accomplished:133• Created X projects134135[Continue with Pro]136[Remind me later] [Downgrade]137```138139---140141## Timing and Frequency142143### When to Show144- After value moment, before frustration145- After activation/aha moment146- When hitting genuine limits147148### When NOT to Show149- During onboarding (too early)150- When they're in a flow151- Repeatedly after dismissal152153### Frequency Rules154- Limit per session155- Cool-down after dismiss (days, not hours)156- Track annoyance signals157158---159160## Upgrade Flow Optimization161162### From Paywall to Payment163- Minimize steps164- Keep in-context if possible165- Pre-fill known information166167### Post-Upgrade168- Immediate access to features169- Confirmation and receipt170- Guide to new features171172---173174## A/B Testing175176### What to Test177- Trigger timing178- Headline/copy variations179- Price presentation180- Trial length181- Feature emphasis182- Design/layout183184### Metrics to Track185- Paywall impression rate186- Click-through to upgrade187- Completion rate188- Revenue per user189- Churn rate post-upgrade190191**For comprehensive experiment ideas**: See [references/experiments.md](references/experiments.md)192193---194195## Anti-Patterns to Avoid196197### Dark Patterns198- Hiding the close button199- Confusing plan selection200- Guilt-trip copy201202### Conversion Killers203- Asking before value delivered204- Too frequent prompts205- Blocking critical flows206- Complicated upgrade process207208---209210## Task-Specific Questions2112121. What's your current free → paid conversion rate?2132. What triggers upgrade prompts today?2143. What features are behind the paywall?2154. What's your "aha moment" for users?2165. What pricing model? (per seat, usage, flat)2176. Mobile app, web app, or both?218219---220221## Related Skills222223- **page-cro**: For public pricing page optimization224- **onboarding-cro**: For driving to aha moment before upgrade225- **ab-test-setup**: For testing paywall variations226227## Technique Map228- **Role definition** - Clarifies operating scope and prevents ambiguous execution.229- **Context enrichment** - Captures required inputs before actions.230- **Output structuring** - Standardizes deliverables for consistent reuse.231- **Step-by-step workflow** - Reduces errors by making execution order explicit.232- **Edge-case handling** - Documents safe fallbacks when assumptions fail.233234## Technique Notes235These techniques improve reliability by making intent, inputs, outputs, and fallback paths explicit. Keep this section concise and additive so existing domain guidance remains primary.236237## Prompt Architect Overlay238### Role Definition239You are the prompt-architect-enhanced specialist for paywall-upgrade-cro, responsible for deterministic execution of this skill's guidance while preserving existing workflow and constraints.240241### Input Contract242- Required: clear user intent and relevant context for this skill.243- Preferred: repository/project constraints, existing artifacts, and success criteria.244- If context is missing, ask focused questions before proceeding.245246### Output Contract247- Provide structured, actionable outputs aligned to this skill's existing format.248- Include assumptions and next steps when appropriate.249- Preserve compatibility with existing sections and related skills.250251### Edge Cases & Fallbacks252- If prerequisites are missing, provide a minimal safe path and request missing inputs.253- If scope is ambiguous, narrow to the highest-confidence sub-task.254- If a requested action conflicts with existing constraints, explain and offer compliant alternatives.
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