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 .agents/product-marketing.md exists (or .claude/product-marketing.md, or the legacy product-marketing-context.md filename, 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:
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
- cro: For public pricing page optimization
- onboarding: For driving to aha moment before upgrade
- ab-testing: For testing paywall variations
Source: coreyhaines31/marketingskills → skills/paywalls/SKILL.md
1---2name: paywalls3description: 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," "in-app pricing," "free users won't upgrade," "trial to paid conversion," or "how do I get users to pay." Use this for any in-product moment where you're asking users to upgrade. Distinct from public pricing pages (see cro) — this focuses on in-product upgrade moments where the user has already experienced value. For pricing decisions, see pricing.4---5
6
7# Paywall and Upgrade Screen CRO
8
9You 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.
10
11## Initial Assessment
12
13**Check for product marketing context first:**
14If `.agents/product-marketing.md` exists (or `.claude/product-marketing.md`, or the legacy `product-marketing-context.md` filename, in older setups), read it before asking questions. Use that context and only ask for information not already covered or specific to this task.
15
16Before providing recommendations, understand:
17
181. **Upgrade Context** - Freemium → Paid? Trial → Paid? Tier upgrade? Feature upsell? Usage limit?
19
202. **Product Model** - What's free? What's behind paywall? What triggers prompts? Current conversion rate?
21
223. **User Journey** - When does this appear? What have they experienced? What are they trying to do?
23
24---
25
26## Core Principles
27
28### 1. Value Before Ask
29- User should have experienced real value first
30- Upgrade should feel like natural next step
31- Timing: After "aha moment," not before
32
33### 2. Show, Don't Just Tell
34- Demonstrate the value of paid features
35- Preview what they're missing
36- Make the upgrade feel tangible
37
38### 3. Friction-Free Path
39- Easy to upgrade when ready
40- Don't make them hunt for pricing
41
42### 4. Respect the No
43- Don't trap or pressure
44- Make it easy to continue free
45- Maintain trust for future conversion
46
47---
48
49## Paywall Trigger Points
50
51### Feature Gates
52When user clicks a paid-only feature:
53- Clear explanation of why it's paid
54- Show what the feature does
55- Quick path to unlock
56- Option to continue without
57
58### Usage Limits
59When user hits a limit:
60- Clear indication of limit reached
61- Show what upgrading provides
62- Don't block abruptly
63
64### Trial Expiration
65When trial is ending:
66- Early warnings (7, 3, 1 day)
67- Clear "what happens" on expiration
68- Summarize value received
69
70### Time-Based Prompts
71After X days of free use:
72- Gentle upgrade reminder
73- Highlight unused paid features
74- Easy to dismiss
75
76---
77
78## Paywall Screen Components
79
801. **Headline** - Focus on what they get: "Unlock [Feature] to [Benefit]"
81
822. **Value Demonstration** - Preview, before/after, "With Pro you could..."
83
843. **Feature Comparison** - Highlight key differences, current plan marked
85
864. **Pricing** - Clear, simple, annual vs. monthly options
87
885. **Social Proof** - Customer quotes, "X teams use this"
89
906. **CTA** - Specific and value-oriented: "Start Getting [Benefit]"
91
927. **Escape Hatch** - Clear "Not now" or "Continue with Free"
93
94---
95
96## Specific Paywall Types
97
98### Feature Lock Paywall
99```
100[Lock Icon]
101This feature is available on Pro
102
103[Feature preview/screenshot]
104
105[Feature name] helps you [benefit]:
106• [Capability]
107• [Capability]
108
109[Upgrade to Pro - $X/mo]
110[Maybe Later]
111```
112
113### Usage Limit Paywall
114```
115You've reached your free limit
116
117[Progress bar at 100%]
118
119Free: 3 projects | Pro: Unlimited
120
121[Upgrade to Pro] [Delete a project]
122```
123
124### Trial Expiration Paywall
125```
126Your trial ends in 3 days
127
128What you'll lose:
129• [Feature used]
130• [Data created]
131
132What you've accomplished:
133• Created X projects
134
135[Continue with Pro]
136[Remind me later] [Downgrade]
137```
138
139---
140
141## Timing and Frequency
142
143### When to Show
144- After value moment, before frustration
145- After activation/aha moment
146- When hitting genuine limits
147
148### When NOT to Show
149- During onboarding (too early)
150- When they're in a flow
151- Repeatedly after dismissal
152
153### Frequency Rules
154- Limit per session
155- Cool-down after dismiss (days, not hours)
156- Track annoyance signals
157
158---
159
160## Upgrade Flow Optimization
161
162### From Paywall to Payment
163- Minimize steps
164- Keep in-context if possible
165- Pre-fill known information
166
167### Post-Upgrade
168- Immediate access to features
169- Confirmation and receipt
170- Guide to new features
171
172---
173
174## A/B Testing
175
176### What to Test
177- Trigger timing
178- Headline/copy variations
179- Price presentation
180- Trial length
181- Feature emphasis
182- Design/layout
183
184### Metrics to Track
185- Paywall impression rate
186- Click-through to upgrade
187- Completion rate
188- Revenue per user
189- Churn rate post-upgrade
190
191**For comprehensive experiment ideas**: See [references/experiments.md](references/experiments.md)
192
193---
194
195## Anti-Patterns to Avoid
196
197### Dark Patterns
198- Hiding the close button
199- Confusing plan selection
200- Guilt-trip copy
201
202### Conversion Killers
203- Asking before value delivered
204- Too frequent prompts
205- Blocking critical flows
206- Complicated upgrade process
207
208---
209
210## Task-Specific Questions
211
2121. 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?
218
219---
220
221## Related Skills
222
223- **churn-prevention**: For cancel flows, save offers, and reducing churn post-upgrade
224- **cro**: For public pricing page optimization
225- **onboarding**: For driving to aha moment before upgrade
226- **ab-testing**: For testing paywall variations
227
228---
229
230**Source:** [`coreyhaines31/marketingskills`](https://github.com/coreyhaines31/marketingskills) → `skills/paywalls/SKILL.md`
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