Imported from lxyeternal/MalSkillBench (Dataset/Skills/benign/paywall-upgrade-cro/SKILL.md). Install upstream with npx skills add lxyeternal/MalSkillBench --skill paywall-upgrade-cro. Copyright stays with the author.

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

Before providing recommendations, understand:

1. Upgrade Context

   • Freemium → Paid conversion
   • Trial → Paid conversion
   • Tier upgrade (Basic → Pro)
   • Feature-specific upsell
   • Usage limit upsell

2. Product Model

   • What's free forever?
   • What's behind the paywall?
   • What triggers upgrade prompts?
   • What's the current conversion rate?

3. User Journey

   • At what point does this appear?
   • What have they experienced already?
   • What are they trying to do when blocked?

Core Principles

1. Value Before Ask

• User should have experienced real value first
• The upgrade should feel like a 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
• Remove barriers to conversion

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 what limit was reached
• Show what upgrading provides
• Option to buy more without full upgrade
• Don't block abruptly

Trial Expiration

When trial is ending:

• Early warnings (7 days, 3 days, 1 day)
• Clear "what happens" on expiration
• Easy re-activation if expired
• Summarize value received

Time-Based Prompts

After X days/sessions of free use:

• Gentle upgrade reminder
• Highlight unused paid features
• Not intrusive—banner or subtle modal
• Easy to dismiss

Context-Triggered

When behavior indicates upgrade fit:

• Power users who'd benefit
• Teams using solo features
• Heavy usage approaching limits
• Inviting teammates

Paywall Screen Components

1. Headline

Focus on what they get, not what they pay:

• "Unlock [Feature] to [Benefit]"
• "Get more [value] with [Plan]"
• Not: "Upgrade to Pro for $X/month"

2. Value Demonstration

Show what they're missing:

• Preview of the feature in action
• Before/after comparison
• "With Pro, you could..." examples
• Specific to their use case if possible

3. Feature Comparison

If showing tiers:

• Highlight key differences
• Current plan clearly marked
• Recommended plan emphasized
• Focus on outcomes, not feature lists

4. Pricing

• Clear, simple pricing
• Annual vs. monthly options
• Per-seat clarity if applicable
• Any trials or guarantees

5. Social Proof (Optional)

• Customer quotes about the upgrade
• "X teams use this feature"
• Success metrics from upgraded users

6. CTA

• Specific: "Upgrade to Pro" not "Upgrade"
• Value-oriented: "Start Getting [Benefit]"
• If trial: "Start Free Trial"

7. Escape Hatch

• Clear "Not now" or "Continue with Free"
• Don't make them feel bad
• "Maybe later" vs. "No, I'll stay limited"

Specific Paywall Types

Feature Lock Paywall

When clicking a paid feature:

[Lock Icon]
This feature is available on Pro

[Feature preview/screenshot]

[Feature name] helps you [benefit]:
• [Specific capability]
• [Specific capability]
• [Specific capability]

[Upgrade to Pro - $X/mo]
[Maybe Later]

Usage Limit Paywall

When hitting a limit:

You've reached your free limit

[Visual: Progress bar at 100%]

Free plan: 3 projects
Pro plan: Unlimited projects

You're active! Upgrade to keep building.

[Upgrade to Pro]    [Delete a project]

Trial Expiration Paywall

When trial is ending:

Your trial ends in 3 days

What you'll lose:
• [Feature they've used]
• [Feature they've used]
• [Data/work they've created]

What you've accomplished:
• Created X projects
• [Specific value metric]

[Continue with Pro - $X/mo]
[Remind me later]    [Downgrade to Free]

Soft Upgrade Prompt

Non-blocking suggestion:

[Banner or subtle modal]

You've been using [Product] for 2 weeks!
Teams like yours get X% more [value] with Pro.

[See Pro Features]    [Dismiss]

Team/Seat Upgrade

When adding users:

Invite your team

Your plan: Solo (1 user)
Team plans start at $X/user

• Shared projects
• Collaboration features
• Admin controls

[Upgrade to Team]    [Continue Solo]

Mobile Paywall Patterns

iOS/Android Conventions

• System-like styling builds trust
• Standard paywall patterns users recognize
• Free trial emphasis common
• Subscription terminology they expect

Mobile-Specific UX

• Full-screen often acceptable
• Swipe to dismiss
• Large tap targets
• Plan selection with clear visual state

App Store Considerations

• Clear pricing display
• Subscription terms visible
• Restore purchases option
• Meet review guidelines

Timing and Frequency

When to Show

• Best: After value moment, before frustration
• After activation/aha moment
• When hitting genuine limits
• When using adjacent-to-paid features

When NOT to Show

• During onboarding (too early)
• When they're in a flow
• Repeatedly after dismissal
• Before they understand the product

Frequency Rules

• Limit to X per session
• Cool-down after dismiss (days, not hours)
• Escalate urgency appropriately (trial end)
• Track annoyance signals (rage clicks, churn)

Upgrade Flow Optimization

From Paywall to Payment

• Minimize steps
• Keep them in-context if possible
• Pre-fill known information
• Show security signals

Plan Selection

• Default to recommended plan
• Annual vs. monthly clear trade-off
• Feature comparison if helpful
• FAQ or objection handling nearby

Checkout

• Minimal fields
• Multiple payment methods
• Trial terms clear
• Easy cancellation visible (builds trust)

Post-Upgrade

• Immediate access to features
• Confirmation and receipt
• Guide to new features
• Celebrate the upgrade

A/B Testing Paywalls

What to Test

• Trigger timing (earlier vs. later)
• Trigger type (feature gate vs. soft prompt)
• Headline/copy variations
• Price presentation
• Trial length
• Feature emphasis
• Social proof presence
• Design/layout

Metrics to Track

• Paywall impression rate
• Click-through to upgrade
• Upgrade completion rate
• Revenue per user
• Churn rate post-upgrade
• Time to upgrade

Output Format

Paywall Design

For each paywall:

• Trigger: When it appears
• Context: What user was doing
• Type: Feature gate, limit, trial, etc.
• Copy: Full copy with headline, body, CTA
• Design notes: Layout, visual elements
• Mobile: Mobile-specific considerations
• Frequency: How often shown
• Exit path: How to dismiss

Upgrade Flow

• Step-by-step screens
• Copy for each step
• Decision points
• Success state

Metrics Plan

What to measure and expected benchmarks

Common Patterns by Business Model

Freemium SaaS

• Generous free tier to build habit
• Feature gates for power features
• Usage limits for volume
• Soft prompts for heavy free users

Free Trial

• Trial countdown prominent
• Value summary at expiration
• Grace period or easy restart
• Win-back for expired trials

Usage-Based

• Clear usage tracking
• Alerts at thresholds (75%, 100%)
• Easy to add more without plan change
• Volume discounts visible

Per-Seat

• Friction at invitation
• Team feature highlights
• Volume pricing clear
• Admin value proposition

Anti-Patterns to Avoid

Dark Patterns

• Hiding the close button
• Confusing plan selection
• Buried downgrade option
• Misleading urgency
• Guilt-trip copy

Conversion Killers

• Asking before value delivered
• Too frequent prompts
• Blocking critical flows
• Unclear pricing
• Complicated upgrade process

Trust Destroyers

• Surprise charges
• Hard-to-cancel subscriptions
• Bait and switch
• Data hostage tactics

Experiment Ideas

Trigger & Timing Experiments

When to Show

• Test trigger timing: after aha moment vs. at feature attempt
• Early trial reminder (7 days) vs. late reminder (1 day before)
• Show after X actions completed vs. after X days
• Test soft prompts at different engagement thresholds
• Trigger based on usage patterns vs. time-based only

Trigger Type

• Hard gate (can't proceed) vs. soft gate (preview + prompt)
• Feature lock vs. usage limit as primary trigger
• In-context modal vs. dedicated upgrade page
• Banner reminder vs. modal prompt
• Exit-intent on free plan pages

Paywall Design Experiments

Layout & Format

• Full-screen paywall vs. modal overlay
• Minimal paywall (CTA-focused) vs. feature-rich paywall
• Single plan display vs. plan comparison
• Image/preview included vs. text-only
• Vertical layout vs. horizontal layout on desktop

Value Presentation

• Feature list vs. benefit statements
• Show what they'll lose (loss aversion) vs. what they'll gain
• Personalized value summary based on usage
• Before/after demonstration
• ROI calculator or value quantification

Visual Elements

• Add product screenshots or previews
• Include short demo video or GIF
• Test illustration vs. product imagery
• Animated vs. static paywall
• Progress visualization (what they've accomplished)

Pricing Presentation Experiments

Price Display

• Show monthly vs. annual vs. both with toggle
• Highlight savings for annual ($ amount vs. % off)
• Price per day framing ("Less than a coffee")
• Show price after trial vs. emphasize "Start Free"
• Display price prominently vs. de-emphasize until click

Plan Options

• Single recommended plan vs. multiple tiers
• Add "Most Popular" badge to target plan
• Test number of visible plans (2 vs. 3)
• Show enterprise/custom tier vs. hide it
• Include one-time purchase option alongside subscription

Discounts & Offers

• First month/year discount for conversion
• Limited-time upgrade offer with countdown
• Loyalty discount based on free usage duration
• Bundle discount for annual commitment
• Referral discount for social proof

Copy & Messaging Experiments

Headlines

• Benefit-focused ("Unlock unlimited projects") vs. feature-focused ("Get Pro features")
• Question format ("Ready to do more?") vs. statement format
• Urgency-based ("Don't lose your work") vs. value-based
• Personalized headline with user's name or usage data
• Social proof headline ("Join 10,000+ Pro users")

CTAs

• "Start Free Trial" vs. "Upgrade Now" vs. "Continue with Pro"
• First person ("Start My Trial") vs. second person ("Start Your Trial")
• Value-specific ("Unlock Unlimited") vs. generic ("Upgrade")
• Add urgency ("Upgrade Today") vs. no pressure
• Include price in CTA vs. separate price display

Objection Handling

• Add money-back guarantee messaging
• Show "Cancel anytime" prominently
• Include FAQ on paywall
• Address specific objections based on feature gated
• Add chat/support option on paywall

Trial & Conversion Experiments

Trial Structure

• 7-day vs. 14-day vs. 30-day trial length
• Credit card required vs. not required for trial
• Full-access trial vs. limited feature trial
• Trial extension offer for engaged users
• Second trial offer for expired/churned users

Trial Expiration

• Countdown timer visibility (always vs. near end)
• Email reminders: frequency and timing
• Grace period after expiration vs. immediate downgrade
• "Last chance" offer with discount
• Pause option vs. immediate cancellation

Upgrade Path

• One-click upgrade from paywall vs. separate checkout
• Pre-filled payment info for returning users
• Multiple payment methods offered
• Quarterly plan option alongside monthly/annual
• Team invite flow for solo-to-team conversion

Personalization Experiments

Usage-Based

• Personalize paywall copy based on features used
• Highlight most-used premium features
• Show usage stats ("You've created 50 projects")
• Recommend plan based on behavior patterns
• Dynamic feature emphasis based on user segment

Segment-Specific

• Different paywall for power users vs. casual users
• B2B vs. B2C messaging variations
• Industry-specific value propositions
• Role-based feature highlighting
• Traffic source-based messaging

Frequency & UX Experiments

Frequency Capping

• Test number of prompts per session
• Cool-down period after dismiss (hours vs. days)
• Escalating urgency over time vs. consistent messaging
• Once per feature vs. consolidated prompts
• Re-show rules after major engagement

Dismiss Behavior

• "Maybe later" vs. "No thanks" vs. "Remind me tomorrow"
• Ask reason for declining
• Offer alternative (lower tier, annual discount)
• Exit survey on dismiss
• Friendly vs. neutral decline copy

Questions to Ask

If you need more context:

1. What's your current free → paid conversion rate?
2. What triggers upgrade prompts today?
3. What features are behind the paywall?
4. What's your "aha moment" for users?
5. What pricing model? (per seat, usage, flat)
6. 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
• analytics-tracking: For measuring upgrade funnel