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Multi-Agent Orchestration

Coordinates multi-agent work with clear owners, work items, evidence, and merge gates.

Agents · Orchestration→
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AI Context Window Audit

Audits Claude Code context overhead and recommends ways to reduce unnecessary loaded content.

Research · Context→
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AI Agent Architecture Audit

Diagnoses agent-system failures across prompts, memory, tools, wrappers, and output delivery.

Research · Agent Architecture→
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AI Skill Discovery

Searches local and external skill sources for existing matches before a new skill is created.

Knowledge Work · Skill Discovery→
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Lead Magnet Strategy

Plans lead magnets around audience needs, buyer stage, capture approach, distribution, and measurement.

Marketing · Lead Generation→
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Ideal Customer Profile

Defines an evidence-based ideal customer profile from research, customer behavior and jobs to be done.

Marketing · Customer Research→
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Go-to-Market Strategy

Builds a launch plan connecting target segments, channels, messaging, milestones and measurable outcomes.

Marketing · Go-to-Market→
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Marketing Campaign Ideas

Generates five campaign concepts with audience messages, channel choices and testable engagement hypotheses.

Marketing · Campaigns→
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Product Growth Loops

Evaluates product-led growth loops and outlines measurable experiments for sharing, collaboration and referrals.

Marketing · Growth→
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Competitor Analysis

Compares competitors using cited evidence and identifies differentiation opportunities and research gaps.

Marketing · Market Research→
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North Star Metric

Defines one customer-value metric and supporting input metrics with clear measurement assumptions.

Marketing · Measurement→
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Product Positioning

Develops differentiated product positioning ideas with audience fit, rationale, and supporting messages.

Marketing · Positioning→
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Product Vision

Draft and compare product vision statements grounded in company values and customer needs.

Business · Product Strategy→
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Go-to-Market Motion Selection

Compare seven acquisition approaches and prioritize a practical go-to-market plan.

Business · Go-to-Market→
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Customer Feedback and JTBD Analysis

Synthesize supplied feedback into evidence-backed themes, jobs to be done and improvement priorities.

Business · Customer Research→
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PESTLE Market Environment Analysis

Map external political, economic, social, technological, legal and environmental factors for a business decision.

Business · Product Strategy→
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Customer Journey Mapping

Map customer touchpoints and friction from awareness through advocacy.

Business · Customer Research→
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Ansoff Growth Options

Compare growth options across existing and new products and markets.

Business · Product Strategy→
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Data Analysis Validation

Review methodology, calculations and conclusions before sharing an analysis.

Data & Analytics · Data Analysis→
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Dataset Profiling

Profile a dataset and identify quality issues and useful follow-up analyses.

Data & Analytics · Data Analysis→
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Statistical Analysis Guidance

Choose descriptive statistics and hypothesis tests while making assumptions and uncertainty explicit.

Data & Analytics · Data Analysis→
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Programmatic SEO Planning

Plan useful SEO pages at scale with a data strategy, templates and twelve complete playbooks.

Marketing · SEO→
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Landing Page and Form Conversion Review

Review marketing pages and forms, prioritize friction fixes and design measurable experiments.

Marketing · Conversion Optimization→
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Paywall and Upgrade Planning

Plan transparent in-product upgrade prompts and experiments after users experience value.

Marketing · Conversion Optimization→
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Signup and Registration Review

Review account creation and trial signup friction while preserving necessary security and consent controls.

Marketing · Conversion Optimization→
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User Onboarding and Activation

Plan the first useful product experience, activation milestones and measurable onboarding experiments.

Marketing · Conversion Optimization→
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Popup and Modal Planning

Design dismissible, accessible conversion overlays with honest offers and measurable frequency rules.

Marketing · Conversion Optimization→
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Lifecycle Email Sequence Planning

Draft a complete lifecycle email sequence with timing, branching, exits and suppression rules.

Marketing · Email Marketing→
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Marketing Campaign Planning

Build a campaign brief with audience, messages, channel choices, calendar, dependencies and measurement.

Marketing · Campaign Planning→
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Marketing Content Drafting

Draft channel-specific marketing content using clear structures, evidence and calls to action.

Marketing · Content Marketing→
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Brand Voice and Content Review

Review drafts against supplied brand guidance and propose specific, prioritized revisions.

Marketing · Brand Strategy→
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Marketing Performance Reporting

Turn supplied campaign or channel metrics into a traceable report with comparisons and testable recommendations.

Marketing · Marketing Analytics→
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Sales Company Research

Research a company or partner and produce a sourced fit hypothesis and draft outreach approach.

Sales · Company Research→
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Company and Contact Enrichment

Resolve company and contact records with field-level evidence, visible coverage limits and explicit match criteria.

Sales · Sales Intelligence→
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Website Information Architecture

Plan page hierarchy, navigation, stable URL patterns and useful internal links for a website.

Marketing · Website Architecture→
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Content Strategy and Editorial Roadmap

Prioritize content pillars, audience questions and distribution plans using evidence and available resources.

Marketing · Content Strategy→
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Product Launch Planning

Plan a scoped product or feature launch across preparation, release and post-launch adoption.

Marketing · Launch Strategy→
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Customer Research and Voice of Customer

Analyze customer evidence and plan interviews or surveys to understand needs, language and buying decisions.

Marketing · Customer Research→
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Community Growth and Member Experience

Plan a community around member value, participation and measurable business goals.

Marketing · Community Marketing→
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Competitor Research Profiles

Build sourced competitor profiles comparing positioning, pricing, product evidence and SEO estimates.

Marketing · Competitive Intelligence→
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Roadmap and Release Communication

Turn approved roadmap and release facts into audience-specific updates, release notes and changelogs.

Product · Roadmaps and Releases→
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Task Packs

Marketing Foundation

Clarify positioning, then turn it into a lead-generation asset.

Marketing Launch

Build an evidence-led marketing plan from ICP and competition through positioning, campaigns, growth and measurement.

Agent Audit Essentials

Diagnose architecture and context, then plan agent-team responsibilities. Memory and cost-runtime reviews are outside this pack.

Conversion and Activation Review

Review the journey from landing page and lead capture through registration, first value and transparent upgrades.

Campaign Content and Brand Review

Plan a campaign, draft its channel content and review the work against actual brand guidance.

Content and Launch Planning

Prioritize an editorial roadmap and plan how to launch and distribute it across suitable channels.

Customer, Market and Community Research

Understand customer needs, compare competitors and plan a community around real member value.

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01 · Category
What the MCP returns at this step
11 · Marketing · Conversion Optimization

Paywall and Upgrade Planning

Plan transparent in-product upgrade prompts and experiments after users experience value.

paywallupgradefreemiumtrialconversion
SaaS Paywall & Upgrade CRO · Original SKILL.md
---
name: paywalls
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," "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.
metadata:
  version: 2.0.0
---

# 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 `.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:

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](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?

---

## 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

When to use

Plan transparent in-product upgrade prompts and experiments after users experience value.

What you get

Upgrade flow recommendations, honest screen copy and a complete experiment guide.

How it works

Identify legitimate triggers, demonstrate actual value, preserve dismissal and compare measurable alternatives.

Requirements

Actual free/paid plan terms, prices, billing periods, trial conditions, usage limits and user journey.
All referenced local guides are included: references/experiments.md. Other named related skills are optional and are not installed by loading this guidance.

M11 review boundaries

Do not apply suggestions to hide or defer material pricing. Disclose billing amount, period, renewal and trial terms before commitment. Countdown timers, loss claims and social proof must be genuine and substantiated. No guilt, trapped dismissal, fake scarcity or unauthorized payment actions.

Starting prompt

Help me with paywall and upgrade planning for [PRODUCT]. First establish Actual free/paid plan terms, prices, billing periods, trial conditions, usage limits and user journey. Do not apply suggestions to hide or defer material pricing. Disclose billing amount, period, renewal and trial terms before commitment. Countdown timers, loss claims and social proof must be genuine and substantiated. No guilt, trapped dismissal, fake scarcity or unauthorized payment actions.

Not for

Pricing-policy approval, payment processing, manipulative checkout or fabricated urgency.

What M11 added

Complete reference packaging, task routing and explicit evidence/transparency boundaries. Do not apply suggestions to hide or defer material pricing. Disclose billing amount, period, renewal and trial terms before commitment. Countdown timers, loss claims and social proof must be genuine and substantiated. No guilt, trapped dismissal, fake scarcity or unauthorized payment actions.

Original authorship remains with coreyhaines31/marketingskills · Original source ↗
Included reference: references/experiments.md

Corey Haines · MIT · SHA-256 5a5760e23c4809ddbc123905e0073ebca2653e7edad29482db810b825d62bd19

# Paywall Experiment Ideas

Comprehensive list of A/B tests and experiments for paywall optimization.

## Contents
- Trigger & Timing Experiments (When to Show, Trigger Type)
- Paywall Design Experiments (Layout & Format, Value Presentation, Visual Elements)
- Pricing Presentation Experiments (Price Display, Plan Options, Discounts & Offers)
- Copy & Messaging Experiments (Headlines, CTAs, Objection Handling)
- Trial & Conversion Experiments (Trial Structure, Trial Expiration, Upgrade Path)
- Personalization Experiments (Usage-Based, Segment-Specific)
- Frequency & UX Experiments (Frequency Capping, Dismiss Behavior)

## 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
MIT License

Copyright (c) 2025 Corey Haines

Permission is hereby granted, free of charge, to any person obtaining a copy
of this software and associated documentation files (the "Software"), to deal
in the Software without restriction, including without limitation the rights
to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
copies of the Software, and to permit persons to whom the Software is
furnished to do so, subject to the following conditions:

The above copyright notice and this permission notice shall be included in all
copies or substantial portions of the Software.

THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
SOFTWARE.
Original license & copyright
MIT License

Copyright (c) 2025 Corey Haines

Permission is hereby granted, free of charge, to any person obtaining a copy
of this software and associated documentation files (the "Software"), to deal
in the Software without restriction, including without limitation the rights
to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
copies of the Software, and to permit persons to whom the Software is
furnished to do so, subject to the following conditions:

The above copyright notice and this permission notice shall be included in all
copies or substantial portions of the Software.

THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
SOFTWARE.
Source SHA-256: d062c03f6b99e76ffaa367a1494ba80098b2033d4d74609b895373a024a8eac1
Snapshot checked: 2026-09-28T11:43:18.366Z
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