Upgrade Conversion

Use the company SSOT when present: follow ../_shared/ssot-consumption.md and the project manifest to load only relevant approved context. Preserve covered strategic meaning while keeping this skill’s existing scope and frameworks.

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.

PMM upgrade responsibility

Own upgrade eligibility, timing, value communication and trial/free-to-paid conversion briefs. Consume accepted go-to-market-strategy and approved pricing-strategy; pricing retains price, packaging, entitlements and commercial policy. Do not invent discounts or repackage plans. Product/Design own in-product implementation; billing/access operations remain external. Measure retained value and conversion quality alongside immediate upgrades.

Initial Assessment

Load the evidence labels: read ../_shared/evidence-gaps.md (relative to this skill's folder) and follow it. Label every claim, benchmark, and number Sourced, Assumed, or Gap. Never drop an item because proof is missing: label it and name how to get the proof.

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:

1. Upgrade Context - Freemium → Paid? Trial → Paid? Tier upgrade? Feature upsell? Usage limit?
2. Product Model - What's free? What's behind paywall? What triggers prompts? Current conversion rate?
3. 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

1. Headline - Focus on what they get: "Unlock [Feature] to [Benefit]"
2. Value Demonstration - Preview, before/after, "With Pro you could..."
3. Feature Comparison - Highlight key differences, current plan marked
4. Pricing - Clear, simple, annual vs. monthly options
5. Social Proof - Customer quotes, "X teams use this"
6. CTA - Specific and value-oriented: "Start Getting [Benefit]"
7. 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

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?

Output Rules

• No em dashes in output.
• Open with the "Inputs and assumptions" note from ../_shared/evidence-gaps.md.
• Label every claim, benchmark, and number Sourced, Assumed, or Gap.
• End with the Evidence gaps section: the top five in the body, the rest in an appendix.
• Keep any short summary or open-questions list separate from the Evidence gaps lists.

Related Skills

• customer-marketing: For cancel flows, save offers, and reducing churn post-upgrade
• acquisition-conversion: For public pricing page optimization
• product-activation: For driving to aha moment before upgrade
• marketing-experimentation: For testing paywall variations