Monetization Design

Monetization Design

Purpose

Design the monetization architecture for a product, including pricing tier structure, paywall placement strategy, subscription infrastructure, and upgrade flow design.

Scope Constraints

Analyzes product feature sets, competitive pricing, and billing architecture patterns. Does not implement payment integrations, modify production billing systems, or access financial data directly.

Inputs

• Product feature set (what exists, what's being built)
• Target user segments and willingness-to-pay estimates
• Competitive pricing landscape
• Existing billing infrastructure (Stripe, RevenueCat, etc.)
• App Store / Play Store requirements for in-app purchases

Input Sanitization

No user-provided values are used in commands or file paths. All inputs are treated as read-only analysis targets.

Procedure

Progress Checklist

• [ ] Step 1: Value metrics defined
• [ ] Step 2: Tier structure designed
• [ ] Step 3: Paywall placement designed
• [ ] Step 4: Upgrade flow designed
• [ ] Step 5: Subscription infrastructure designed
• [ ] Step 6: Retention mechanics designed

Step 1: Define Value Metrics

Identify what users pay for:

• Usage-based: API calls, storage, messages, seats
• Feature-based: Advanced features, integrations, priority support
• Outcome-based: Projects, exports, reports generated
• Choose the metric that scales with the value the user receives

Step 2: Design Tier Structure

Create a pricing ladder:

• Free tier: Generous enough to create habit and demonstrate value
• Pro tier: For power users and small teams — the "sweet spot"
• Enterprise tier: For organizations — custom pricing, SSO, audit logs
• Apply anchoring: the Pro tier should look like a great deal compared to Enterprise
• Apply decoy effect if appropriate: a tier that makes the target tier look better

Step 3: Design Paywall Placement

Determine where paywalls appear:

• Feature gating: Advanced features locked behind upgrade
• Usage limits: Free tier gets N units/month, Pro gets unlimited
• Soft paywalls: Show the feature, let them try it, then gate on save/export
• Hard paywalls: Block access entirely until upgrade
• Rule: Paywalls should appear when users want more, not when they want basic

Step 4: Design Upgrade Flow

Create the conversion experience:

• Trigger moment: User hits a limit or discovers a locked feature
• Value presentation: Show what they'll get (not just what they're paying)
• Pricing page: Clear comparison table, recommended tier highlighted
• Checkout flow: Minimize steps — ideally 1-2 clicks from trigger to purchase
• Trial option: 7-14 day free trial with full access, credit card optional vs required

Step 5: Design Subscription Infrastructure

Technical architecture:

• Payment provider: Stripe, RevenueCat, Paddle, or platform-native (App Store, Play Store)
• Entitlement system: How the app checks what the user has access to
• Webhook handling: Subscription created, renewed, cancelled, payment failed
• Grace period: What happens when payment fails (dunning flow)
• Platform compliance: App Store requirements for subscription management

Step 6: Design Retention Mechanics

Reduce subscription churn:

• Cancellation flow: Ask why, offer alternatives (pause, downgrade, discount)
• Win-back offers: Discount email after cancellation
• Annual discount: Incentivize annual plans (typically 20% discount)
• Usage reinforcement: Show users the value they've received ("You saved 10 hours this month")

> Compaction resilience: If context was lost during a long session, re-read the Inputs section to reconstruct what product is being analyzed, check the Progress Checklist for completed steps, then resume from the earliest incomplete step.

Output Format

# Monetization Architecture

## Value Metric
**Primary metric:** [What users pay for]
**Scaling:** [How it grows with usage]

## Tier Structure
| | Free | Pro ($X/mo) | Enterprise |
|---|------|------------|------------|
| [Feature 1] | Limited | Unlimited | Unlimited |
| [Feature 2] | No | Yes | Yes |
| [Feature 3] | No | No | Yes |
| Support | Community | Email | Dedicated |

## Paywall Map
| Feature/Limit | Type | Trigger | User Experience |
|--------------|------|---------|-----------------|
| [Feature] | Soft | Usage limit hit | Show result, gate export |
| [Feature] | Hard | Feature tap | Upgrade modal with trial |

## Upgrade Flow
1. User hits [trigger]
2. [Inline upgrade prompt / modal / pricing page]
3. [Plan selection with trial option]
4. [Checkout — X steps]
5. [Success confirmation + unlock]

## Subscription Infrastructure
**Provider:** [Stripe / RevenueCat / etc.]
**Entitlement check:** [How the app verifies access]
**Dunning flow:** [What happens on payment failure]

## Retention Strategy
| Churn Signal | Intervention | Timing |
|-------------|-------------|--------|
| Cancellation initiated | Exit survey + discount offer | Immediate |
| Payment failed | Dunning email sequence | Day 1, 3, 7 |

Handoff

• Hand off to growth-engineering if onboarding funnel optimization or A/B test instrumentation needs arise during monetization analysis.
• Hand off to messaging-strategy if upgrade prompt copy, paywall messaging, or cancellation flow language needs refinement.

Quality Checks

• [ ] Free tier is generous enough to demonstrate value and create habit
• [ ] Paywall placement occurs at "want more" moments, not "need basic" moments
• [ ] Upgrade flow is 2 clicks or fewer from trigger to checkout
• [ ] Subscription infrastructure handles renewal, cancellation, and payment failure
• [ ] App Store / Play Store subscription requirements are met (if applicable)
• [ ] Retention mechanics include cancellation flow and win-back strategy

Evolution Notes

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: dtsong
• Source: dtsong/my-claude-setup
• License: MIT

Install and usage instructions live in the source repository linked above.