coreyhaines31/pricing

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.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.

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?

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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.

Don't anchor on the wrong things:

• Not competitor-based — matching a competitor's price copies their strategy, not their economics. It's a data point, not a target.
• Not cost-based — cost is a floor, never the basis. Value + differentiation set the price.

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Initial Pricing — "Pick a Price You Can Learn From"

The frameworks below (value metrics, tiers, Van Westendorp) are for optimizing a price. On day one you don't have a price to optimize — you have a bet to place. The goal of your first price is learning, not precision. Pick a number, ship it, and let real buyers tell you if it's wrong.

The $10 / $100 / $1,000 rule of thumb

When you have nothing to go on, start with the order of magnitude that matches who you serve:

• ~$10/mo — prosumer / individual, high volume, low touch
• ~$100/mo — SMB / team tool, the SaaS default
• ~$1,000/mo — mid-market / business-critical / sales-assisted

Pick the bucket by who the customer is and how much value you deliver, then start near the round number. You can move within the bucket fast once you have signal.

Avoid the $9 trap

Resist the urge to price ultra-low (e.g. $9/mo) to reduce friction. Ultra-low pricing:

• Creates false traction — signups that look like validation but come from people who'd never pay a real price
• Traps you — it's far harder to raise a price 5–10x later than to have started higher, and your cheapest customers churn most and complain loudest (see references/pricing-models.md on low-price retention)

Round-and-slightly-higher beats clever-and-cheap.

"Just charge $50 and see what happens"

When early Intercom agonized over pricing, Jason Fried's advice was essentially: just charge $50 and see what happens. Stop modeling; get a real signal. If people pay without flinching, raise it. If nobody bites, you've learned something for the cost of a week, not a quarter.

For the eight ways to structure how you charge (flat, usage, tier, user, feature, credit, outcome, hybrid) and the value/price ratio: See references/pricing-models.md.

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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

| Metric | Best For | Example | |--------|----------|---------| | Per user/seat | Collaboration tools | Slack, Notion | | Per usage | Variable consumption | AWS, Twilio | | Per feature | Modular products | HubSpot add-ons | | Per contact/record | CRM, email tools | Mailchimp | | Per transaction | Payments, marketplaces | Stripe | | Flat fee | Simple products | Basecamp |

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

The value metric picks the pricing model. Once you know what scales with value, choose how to charge on it — flat, usage, tier, user, feature, credit, outcome, or a hybrid. See references/pricing-models.md.

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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

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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

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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

Rollout Methodology

A price change is a rollout, not a switch you flip. Sequence it to de-risk:

1. Test on new customers first. Raise the price only for new signups and watch conversion. New customers have no anchor and no relationship at stake, so they give you a clean read on whether the market accepts the number — before you touch a single existing account.
2. Don't reflexively grandfather forever. Grandfathering feels kind, but it can leave enormous money on the table. Run the math: a customer paying $50/mo who should be at $250/mo is a $2,400/yr gap — and $200/mo you're subsidizing indefinitely across your whole base. Grandfather as a transition (a grace period), not a permanent exemption.
3. Roll out small, then gradually. Move 5–10% of existing customers to the new price first. Watch churn and support volume for a cycle, then expand in staggered waves. A staggered rollout contains the blast radius and gives you an off-ramp if churn spikes.
4. Communicate the why, months ahead, with a generous offer. Tell customers why the price is changing (usually: more value shipped) well in advance. Soften it: lock-in-the-old-price-if-you-upgrade-to-annual-now, an extended grace window, or a one-time credit. Advance notice + a generous option converts a resentment moment into a loyalty one.

Expect — and accept — some churn. The customers most likely to leave over a justified increase are usually your least-profitable, highest-support, most price-sensitive accounts.

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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)

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Pricing Page Teardown

When someone wants to audit an existing pricing page for clarity, transparency, and AI-readability (not the pricing strategy itself, and not conversion-rate optimization — that's cro), run a teardown that scores it across two axes and returns prioritized fixes:

• Human buyer experience — value-prop clarity, plan differentiation, cognitive load, trust signals, pricing psychology, and price transparency.
• AI-agent readiness — whether the LLMs and agents that increasingly shortlist and compare tools can actually read and quote your pricing: machine-readable prices (not locked in an image or behind "Contact us"), extractable FAQ/objection coverage, per-tier depth stated in text, and structured data. Buyers now ask ChatGPT/Perplexity/Claude "what's the best X and what does it cost?" before visiting — a pricing page an agent can't parse loses deals you never see.

Fast check — the "paste test": give the pricing URL to a browsing-capable AI (Perplexity, ChatGPT with search, Claude with web) — or paste the rendered page text — and ask "what are the plans and prices?" A clean miss means agents fetching your page will struggle too (a heuristic, not proof every agent fails).

The AI-readiness fixes are usually high-impact, low-effort (put prices in text, add Offer schema). Hand implementation to schema (Product/Offer JSON-LD) and ai-seo (extractability, AI-bot access, llms.txt).

For the full 10-dimension rubric, scoring, and report template: See references/pricing-page-teardown.md. (AI-agent-readiness lens adapted from Kyle Poyar / Growth Unhinged.)

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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

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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?

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Related Skills

• churn-prevention: For cancel flows, save offers, and reducing revenue churn
• cro: For optimizing pricing page conversion
• ai-seo: For making the pricing page extractable/citable by AI (the teardown's AI-agent-readiness axis)
• schema: For Product/Offer structured data so machines can read your tiers and prices
• copywriting: For pricing page copy
• marketing-psychology: For pricing psychology principles
• ab-testing: For testing pricing changes
• revops: For deal desk processes and pipeline pricing
• sales-enablement: For proposal templates and pricing presentations