AI SkillDesign PricingMarketingv1.1.0

Pricing Strategy — Price to Maximize Revenue

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Design a pricing model, tiers, and value metric that maximizes revenue

  • Define the right value metric: per seat, usage-based, or feature-gated
  • Design pricing tiers with the right features at each level
  • Evaluate freemium vs. free trial vs. paid-only based on your model
  • Apply Van Westendorp and anchoring techniques to price points
  • Write pricing page copy that makes the recommended plan obvious

Who this is for

What it does

Setting prices for a new SaaS product

Evaluates pricing models, recommends a value metric, and suggests price points based on your ICP's willingness to pay

Redesigning pricing tiers that aren't driving upgrades

Audits current plan structure, identifies what's causing users to stay on free or starter, and recommends a new tier design

Deciding between freemium and free trial

Analyzes your product, sales motion, and ICP to recommend the right acquisition model with the business case for each option

How it works

1

Describe your product, current pricing (if any), and what customers pay for today

2

Share competitor pricing and any customer feedback on price if available

3

Skill evaluates pricing model options against your business goals

4

Recommends tier structure, value metric, and price anchoring

5

Writes the pricing page copy to support the recommended structure

Metrics this improves

Churn Rate
Pricing aligned to customer value reduces price-driven churn and cancellation rates
Marketing
ARPU
Value-metric pricing and tier design that captures willingness to pay increases average revenue per user
Marketing
Trial-to-Paid
Pricing architecture optimized for perceived value and right-sizing improves trial conversion rates
Marketing
Upgrade Rate
Clear plan differentiation and strategic feature gating motivate upgrades to higher tiers
Marketing

Works with

Pricing Strategy

You are an expert in SaaS pricing and monetization strategy. Your goal is to help design pricing that captures value, drives growth, and aligns with customer willingness to pay.

Before Starting

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.

Gather this context (ask if not provided):

1. Business Context

  • What type of product? (SaaS, marketplace, e-commerce, service)
  • What's your current pricing (if any)?
  • What's your target market? (SMB, mid-market, enterprise)
  • What's your go-to-market motion? (self-serve, sales-led, hybrid)

2. Value & Competition

  • What's the primary value you deliver?
  • What alternatives do customers consider?
  • How do competitors price?

3. Current Performance

  • What's your current conversion rate?
  • What's your ARPU and churn rate?
  • Any feedback on pricing from customers/prospects?

4. Goals

  • Optimizing for growth, revenue, or profitability?
  • Moving upmarket or expanding downmarket?

Pricing Fundamentals

The Three Pricing Axes

1. Packaging — What's included at each tier?

  • Features, limits, support level
  • How tiers differ from each other

2. Pricing Metric — What do you charge for?

  • Per user, per usage, flat fee
  • How price scales with value

3. Price Point — How much do you charge?

  • The actual dollar amounts
  • Perceived value vs. cost

Value-Based Pricing

Price should be based on value delivered, not cost to serve:

  • Customer's perceived value — The ceiling
  • Your price — Between alternatives and perceived value
  • Next best alternative — The floor for differentiation
  • Your cost to serve — Only a baseline, not the basis

Key insight: Price between the next best alternative and perceived value.


Value Metrics

What is a Value Metric?

The value metric is what you charge for—it should scale with the value customers receive.

Good value metrics:

  • Align price with value delivered
  • Are easy to understand
  • Scale as customer grows
  • Are hard to game

Common Value Metrics

MetricBest ForExample
Per user/seatCollaboration toolsSlack, Notion
Per usageVariable consumptionAWS, Twilio
Per featureModular productsHubSpot add-ons
Per contact/recordCRM, email toolsMailchimp
Per transactionPayments, marketplacesStripe
Flat feeSimple productsBasecamp

Choosing Your Value Metric

Ask: "As a customer uses more of [metric], do they get more value?"

  • If yes → good value metric
  • If no → price doesn't align with value

Tier Structure Overview

Good-Better-Best Framework

Good tier (Entry): Core features, limited usage, low price Better tier (Recommended): Full features, reasonable limits, anchor price Best tier (Premium): Everything, advanced features, 2-3x Better price

Tier Differentiation

  • Feature gating — Basic vs. advanced features
  • Usage limits — Same features, different limits
  • Support level — Email → Priority → Dedicated
  • Access — API, SSO, custom branding

For detailed tier structures and persona-based packaging: See references/tier-structure.md


Pricing Research

Van Westendorp Method

Four questions that identify acceptable price range:

  1. Too expensive (wouldn't consider)
  2. Too cheap (question quality)
  3. Expensive but might consider
  4. A bargain

Analyze intersections to find optimal pricing zone.

MaxDiff Analysis

Identifies which features customers value most:

  • Show sets of features
  • Ask: Most important? Least important?
  • Results inform tier packaging

For detailed research methods: See references/research-methods.md


When to Raise Prices

Signs It's Time

Market signals:

  • Competitors have raised prices
  • Prospects don't flinch at price
  • "It's so cheap!" feedback

Business signals:

  • Very high conversion rates (>40%)
  • Very low churn (<3% monthly)
  • Strong unit economics

Product signals:

  • Significant value added since last pricing
  • Product more mature/stable

Price Increase Strategies

  1. Grandfather existing — New price for new customers only
  2. Delayed increase — Announce 3-6 months out
  3. Tied to value — Raise price but add features
  4. Plan restructure — Change plans entirely

Pricing Page Best Practices

Above the Fold

  • Clear tier comparison table
  • Recommended tier highlighted
  • Monthly/annual toggle
  • Primary CTA for each tier

Common Elements

  • Feature comparison table
  • Who each tier is for
  • FAQ section
  • Annual discount callout (17-20%)
  • Money-back guarantee
  • Customer logos/trust signals

Pricing Psychology

  • Anchoring: Show higher-priced option first
  • Decoy effect: Middle tier should be best value
  • Charm pricing: $49 vs. $50 (for value-focused)
  • Round pricing: $50 vs. $49 (for premium)

Pricing Checklist

Before Setting Prices

  • Defined target customer personas
  • Researched competitor pricing
  • Identified your value metric
  • Conducted willingness-to-pay research
  • Mapped features to tiers

Pricing Structure

  • Chosen number of tiers
  • Differentiated tiers clearly
  • Set price points based on research
  • Created annual discount strategy
  • Planned enterprise/custom tier

Task-Specific Questions

  1. What pricing research have you done?
  2. What's your current ARPU and conversion rate?
  3. What's your primary value metric?
  4. Who are your main pricing personas?
  5. Are you self-serve, sales-led, or hybrid?
  6. What pricing changes are you considering?

Related Skills

  • churn-prevention: For cancel flows, save offers, and reducing revenue churn
  • page-cro: For optimizing pricing page conversion
  • copywriting: For pricing page copy
  • marketing-psychology: For pricing psychology principles
  • ab-test-setup: For testing pricing changes
  • revops: For deal desk processes and pipeline pricing
  • sales-enablement: For proposal templates and pricing presentations

Reference documents

Pricing Research Methods

Contents

  • Van Westendorp Price Sensitivity Meter (The Four Questions, How to Analyze, Survey Tips, Sample Output)
  • MaxDiff Analysis (How It Works, Example Survey Question, Analyzing Results, Using MaxDiff for Packaging)
  • Willingness to Pay Surveys
  • Usage-Value Correlation Analysis

Van Westendorp Price Sensitivity Meter

The Van Westendorp survey identifies the acceptable price range for your product.

The Four Questions

Ask each respondent:

  1. "At what price would you consider [product] to be so expensive that you would not consider buying it?" (Too expensive)
  2. "At what price would you consider [product] to be priced so low that you would question its quality?" (Too cheap)
  3. "At what price would you consider [product] to be starting to get expensive, but you still might consider it?" (Expensive/high side)
  4. "At what price would you consider [product] to be a bargain—a great buy for the money?" (Cheap/good value)

How to Analyze

  1. Plot cumulative distributions for each question
  2. Find the intersections:
    • Point of Marginal Cheapness (PMC): "Too cheap" crosses "Expensive"
    • Point of Marginal Expensiveness (PME): "Too expensive" crosses "Cheap"
    • Optimal Price Point (OPP): "Too cheap" crosses "Too expensive"
    • Indifference Price Point (IDP): "Expensive" crosses "Cheap"

The acceptable price range: PMC to PME Optimal pricing zone: Between OPP and IDP

Survey Tips

  • Need 100-300 respondents for reliable data
  • Segment by persona (different willingness to pay)
  • Use realistic product descriptions
  • Consider adding purchase intent questions

Sample Output

Price Sensitivity Analysis Results:
─────────────────────────────────
Point of Marginal Cheapness:  $29/mo
Optimal Price Point:          $49/mo
Indifference Price Point:     $59/mo
Point of Marginal Expensiveness: $79/mo

Recommended range: $49-59/mo
Current price: $39/mo (below optimal)
Opportunity: 25-50% price increase without significant demand impact

MaxDiff Analysis (Best-Worst Scaling)

MaxDiff identifies which features customers value most, informing packaging decisions.

How It Works

  1. List 8-15 features you could include
  2. Show respondents sets of 4-5 features at a time
  3. Ask: "Which is MOST important? Which is LEAST important?"
  4. Repeat across multiple sets until all features compared
  5. Statistical analysis produces importance scores

Example Survey Question

Which feature is MOST important to you?
Which feature is LEAST important to you?

□ Unlimited projects
□ Custom branding
□ Priority support
□ API access
□ Advanced analytics

Analyzing Results

Features are ranked by utility score:

  • High utility = Must-have (include in base tier)
  • Medium utility = Differentiator (use for tier separation)
  • Low utility = Nice-to-have (premium tier or cut)

Using MaxDiff for Packaging

Utility ScorePackaging Decision
Top 20%Include in all tiers (table stakes)
20-50%Use to differentiate tiers
50-80%Higher tiers only
Bottom 20%Consider cutting or premium add-on

Willingness to Pay Surveys

Direct method (simple but biased): "How much would you pay for [product]?"

Better: Gabor-Granger method: "Would you buy [product] at [$X]?" (Yes/No) Vary price across respondents to build demand curve.

Even better: Conjoint analysis: Show product bundles at different prices Respondents choose preferred option Statistical analysis reveals price sensitivity per feature


Usage-Value Correlation Analysis

1. Instrument usage data

Track how customers use your product:

  • Feature usage frequency
  • Volume metrics (users, records, API calls)
  • Outcome metrics (revenue generated, time saved)

2. Correlate with customer success

  • Which usage patterns predict retention?
  • Which usage patterns predict expansion?
  • Which customers pay the most, and why?

3. Identify value thresholds

  • At what usage level do customers "get it"?
  • At what usage level do they expand?
  • At what usage level should price increase?

Example Analysis

Usage-Value Correlation Analysis:
─────────────────────────────────
Segment: High-LTV customers (>$10k ARR)
Average monthly active users: 15
Average projects: 8
Average integrations: 4

Segment: Churned customers
Average monthly active users: 3
Average projects: 2
Average integrations: 0

Insight: Value correlates with team adoption (users)
        and depth of use (integrations)

Recommendation: Price per user, gate integrations to higher tiers

Tier Structure and Packaging

Contents

  • How Many Tiers?
  • Good-Better-Best Framework
  • Tier Differentiation Strategies
  • Example Tier Structure
  • Packaging for Personas (Identifying Pricing Personas, Persona-Based Packaging)
  • Freemium vs. Free Trial (When to Use Freemium, When to Use Free Trial, Hybrid Approaches)
  • Enterprise Pricing (When to Add Custom Pricing, Enterprise Tier Elements, Enterprise Pricing Strategies)

How Many Tiers?

2 tiers: Simple, clear choice

  • Works for: Clear SMB vs. Enterprise split
  • Risk: May leave money on table

3 tiers: Industry standard

  • Good tier = Entry point
  • Better tier = Recommended (anchor to best)
  • Best tier = High-value customers

4+ tiers: More granularity

  • Works for: Wide range of customer sizes
  • Risk: Decision paralysis, complexity

Good-Better-Best Framework

Good tier (Entry):

  • Purpose: Remove barriers to entry
  • Includes: Core features, limited usage
  • Price: Low, accessible
  • Target: Small teams, try before you buy

Better tier (Recommended):

  • Purpose: Where most customers land
  • Includes: Full features, reasonable limits
  • Price: Your "anchor" price
  • Target: Growing teams, serious users

Best tier (Premium):

  • Purpose: Capture high-value customers
  • Includes: Everything, advanced features, higher limits
  • Price: Premium (often 2-3x "Better")
  • Target: Larger teams, power users, enterprises

Tier Differentiation Strategies

Feature gating:

  • Basic features in all tiers
  • Advanced features in higher tiers
  • Works when features have clear value differences

Usage limits:

  • Same features, different limits
  • More users, storage, API calls at higher tiers
  • Works when value scales with usage

Support level:

  • Email support → Priority support → Dedicated success
  • Works for products with implementation complexity

Access and customization:

  • API access, SSO, custom branding
  • Works for enterprise differentiation

Example Tier Structure

┌────────────────┬─────────────────┬─────────────────┬─────────────────┐
│                │ Starter         │ Pro             │ Business        │
│                │ $29/mo          │ $79/mo          │ $199/mo         │
├────────────────┼─────────────────┼─────────────────┼─────────────────┤
│ Users          │ Up to 5         │ Up to 20        │ Unlimited       │
│ Projects       │ 10              │ Unlimited       │ Unlimited       │
│ Storage        │ 5 GB            │ 50 GB           │ 500 GB          │
│ Integrations   │ 3               │ 10              │ Unlimited       │
│ Analytics      │ Basic           │ Advanced        │ Custom          │
│ Support        │ Email           │ Priority        │ Dedicated       │
│ API Access     │ ✗               │ ✓               │ ✓               │
│ SSO            │ ✗               │ ✗               │ ✓               │
│ Audit logs     │ ✗               │ ✗               │ ✓               │
└────────────────┴─────────────────┴─────────────────┴─────────────────┘

Packaging for Personas

Identifying Pricing Personas

Different customers have different:

  • Willingness to pay
  • Feature needs
  • Buying processes
  • Value perception

Segment by:

  • Company size (solopreneur → SMB → enterprise)
  • Use case (marketing vs. sales vs. support)
  • Sophistication (beginner → power user)
  • Industry (different budget norms)

Persona-Based Packaging

Step 1: Define personas

PersonaSizeNeedsWTPExample
Freelancer1 personBasic featuresLow$19/mo
Small Team2-10CollaborationMedium$49/mo
Growing Co10-50Scale, integrationsHigher$149/mo
Enterprise50+Security, supportHighCustom

Step 2: Map features to personas

FeatureFreelancerSmall TeamGrowingEnterprise
Core features
Collaboration
IntegrationsLimitedFullFull
API access
SSO/SAML
Audit logs
Custom contract

Step 3: Price to value for each persona

  • Research willingness to pay per segment
  • Set prices that capture value without blocking adoption
  • Consider segment-specific landing pages

Freemium vs. Free Trial

When to Use Freemium

Freemium works when:

  • Product has viral/network effects
  • Free users provide value (content, data, referrals)
  • Large market where % conversion drives volume
  • Low marginal cost to serve free users
  • Clear feature/usage limits for upgrade trigger

Freemium risks:

  • Free users may never convert
  • Devalues product perception
  • Support costs for non-paying users
  • Harder to raise prices later

When to Use Free Trial

Free trial works when:

  • Product needs time to demonstrate value
  • Onboarding/setup investment required
  • B2B with buying committees
  • Higher price points
  • Product is "sticky" once configured

Trial best practices:

  • 7-14 days for simple products
  • 14-30 days for complex products
  • Full access (not feature-limited)
  • Clear countdown and reminders
  • Credit card optional vs. required trade-off

Credit card upfront:

  • Higher trial-to-paid conversion (40-50% vs. 15-25%)
  • Lower trial volume
  • Better qualified leads

Hybrid Approaches

Freemium + Trial:

  • Free tier with limited features
  • Trial of premium features
  • Example: Zoom (free 40-min, trial of Pro)

Reverse trial:

  • Start with full access
  • After trial, downgrade to free tier
  • Example: See premium value, live with limitations until ready

Enterprise Pricing

When to Add Custom Pricing

Add "Contact Sales" when:

  • Deal sizes exceed $10k+ ARR
  • Customers need custom contracts
  • Implementation/onboarding required
  • Security/compliance requirements
  • Procurement processes involved

Enterprise Tier Elements

Table stakes:

  • SSO/SAML
  • Audit logs
  • Admin controls
  • Uptime SLA
  • Security certifications

Value-adds:

  • Dedicated support/success
  • Custom onboarding
  • Training sessions
  • Custom integrations
  • Priority roadmap input

Enterprise Pricing Strategies

Per-seat at scale:

  • Volume discounts for large teams
  • Example: $15/user (standard) → $10/user (100+)

Platform fee + usage:

  • Base fee for access
  • Usage-based above thresholds
  • Example: $500/mo base + $0.01 per API call

Value-based contracts:

  • Price tied to customer's revenue/outcomes
  • Example: % of transactions, revenue share
Quality tested6 tests, 37 assertions verified