pricing-strategy

When the user wants help with pricing decisions, packaging, or monetization strategy. Also use when the user mentions 'pricing,' 'pricing tiers,' 'freemium,' 'free trial,' 'packaging,' 'price increase,' 'value metric,' 'Van Westendorp,' 'willingness to pay,' 'monetization,' 'how much should I charge,' 'my pricing is wrong,' 'pricing page,' 'annual vs monthly,' 'per seat pricing,' or 'should I offer a free plan.' Use this whenever someone is figuring out what to charge or how to structure their plans. For in-app upgrade screens, see paywall-upgrade-cro.

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Install skill "pricing-strategy" with this command: npx skills add coreyhaines31/marketingskills/coreyhaines31-marketingskills-pricing-strategy

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

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pricing-strategy | V50.AI