Convert free users to paid (or upgrade users to higher tiers) at moments when they've experienced enough value to justify the commitment.
Step 0: Context Check
Read .agents/product-marketing-context.md (or .claude/product-marketing-context.md
on older setups) first. Only ask for what isn't there.
Identify before recommending:
- Upgrade context — freemium → paid? Trial → paid? Tier upgrade? Feature upsell? Usage limit?
- Product model — what's free? What's behind the 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
- Value before ask. The user should have experienced real value first. Upgrade should feel like a natural next step. Timing: after the aha moment, not before.
- Show, don't just tell. Demonstrate the value of paid features. Preview what they're missing. Make the upgrade feel tangible.
- Friction-free path. Easy to upgrade when ready. Don't make them hunt for pricing.
- Respect the no. Don't trap or pressure. Make it easy to continue free. Keep trust for future conversion.
Trigger Points
Feature Gates
When the 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 the user hits a limit:
- Clear indication of limit reached
- Show what upgrading provides
- Don't block abruptly
Trial Expiration
When the 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 a value moment, before frustration
- After activation / aha moment
- When hitting genuine limits
When NOT to Show
- During onboarding (too early)
- Mid-flow
- Repeatedly after dismissal
Frequency Rules
- Cap per session
- Cool-down after dismiss (days, not hours)
- Track annoyance signals
Upgrade Flow Optimization
From Paywall to Payment
- Minimize steps
- Keep in-context where 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
Comprehensive experiments: references/experiments.md.
Anti-Patterns
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
- Current free → paid conversion rate?
- What triggers upgrade prompts today?
- What features sit behind the paywall?
- What's the user's aha moment?
- Pricing model? (Per seat, usage, flat.)
- Mobile app, web app, or both?
Related Skills
- iblai-marketing-churn-prevention: Cancel flows, save offers, post-upgrade churn
- iblai-marketing-page-cro: Public pricing page optimization
- iblai-marketing-onboarding-cro: Driving to aha moment before upgrade
- iblai-marketing-ab-test-setup: Testing paywall variations