maximoseo/paywall-upgrade-cro
.agents/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," 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.
testing
Updated Apr 17, 2026
$ install --global
skillsauthnpx skillsauth add maximoseo/html-redesign-vps paywall-upgrade-croInstall this skill globally with one command. Works with Claude Code, Cursor, and Windsurf.
Security Scan Results
3 of 9 scanners reported clean
Some scanners were skipped, did not run, or reported a non-clean status. Review each row below.
3
Scanners Passed
9
Scanners in report
Clean
TrivyContainer and dependency vulnerability scanner
95%
Clean
SemgrepStatic code analysis for vulnerabilities
95%
Clean
mcp-scan (Snyk)Model Context Protocol security validation
95%
Skipped
Snyk (dep)Open source security scanning
50%
Skipped
Socket.devSupply chain security analysis
50%
Skipped
VirusTotalMulti-engine malware detection
50%
Skipped
CrowdStrikeAdvanced threat intelligence
50%
Skipped
OSV-ScannerOpen Source Vulnerability database check
50%
Skipped
OWASP Dep-Check
50%
Last scanned: Mar 29, 2026, 6:48 PM38.5s2 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," 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.
- version:
- 1.0.0
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 .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
- 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
Related Skills
maximoseo/product-marketing-context
development
VerifiedTrustedCommunity
When the user wants to create or update their product marketing context document. Also use when the user mentions 'product context,' 'marketing context,' 'set up context,' 'positioning,' or wants to avoid repeating foundational information across marketing tasks. Creates `.claude/product-marketing-context.md` that other marketing skills reference.
SKILL.mdUpdated Apr 17, 2026
maximoseo/product-hunt-launch
testing
VerifiedTrustedCommunity
Product Hunt launch optimization with specific specs, timing, and gallery strategy. Covers taglines, gallery images, maker comments, and launch day tactics. Use for: product launches, startup launches, side project launches, Product Hunt optimization. Triggers: product hunt, ph launch, product hunt launch, launch strategy, product launch, startup launch, product hunt tips, product hunt gallery, ph optimization, launch day, product hunt maker
SKILL.mdUpdated Apr 17, 2026
maximoseo/product-changelog
development
VerifiedTrustedCommunity
Product changelog and release notes that users actually read. Covers categorization, user-facing language, visuals, and distribution. Use for: release notes, changelogs, product updates, feature announcements, versioning. Triggers: changelog, release notes, product update, version notes, what's new, feature announcement, product changelog, update log, release announcement, version release, product release, ship notes
SKILL.mdUpdated Apr 17, 2026
maximoseo/pricing-strategy
testing
VerifiedTrustedCommunity
When the user wants help with pricing decisions, packaging, or monetization strategy. Also use when the user mentions 'pricing,' 'pricing tiers,' 'freemium,' 'free trial,' 'packaging,' 'price increase,' 'value metric,' 'Van Westendorp,' 'willingness to pay,' or 'monetization.' This skill covers pricing research, tier structure, and packaging strategy.
SKILL.mdUpdated Apr 17, 2026