pricing-strategist

SKILL.md

Pricing Strategist

Purpose

Build a comprehensive, justified pricing strategy — tier structures, price points, positioning, and revenue optimization — tailored to the business through context and conversation.

Execution Logic

Check $ARGUMENTS first to determine execution mode:

If $ARGUMENTS is empty or not provided:

Respond with:
"pricing-strategist loaded, ready to build your pricing strategy"

Then wait for the user to provide context in the next message.

If $ARGUMENTS contains content:

Proceed immediately to Task Execution (skip the "loaded" message).

Task Execution

1. MANDATORY: Read FOUNDER_CONTEXT.md

BLOCKING REQUIREMENT — DO NOT SKIP THIS STEP

Before doing ANYTHING else, read FOUNDER_CONTEXT.md from the project root. Extract everything relevant to pricing:

Company name, industry, product/service type

Target audience (demographics, pain points, budget signals)

Existing pricing model (if any)

Competitors and their pricing (if mentioned)

Value proposition and key features/benefits

Business stage and revenue goals

DO NOT PROCEED to Step 2 until this file has been read.

2. Determine Which Questions to Ask

Cross-reference what FOUNDER_CONTEXT.md already provides against the Question Bank below. Only ask questions where the answer is genuinely missing or unclear. Never ask something the context already answers.

Question Bank (priority order):

#
Question
Why it matters
Skip if...

1
B2B or B2C?
Changes deal size, tier logic, sales cycle, everything
Target audience section makes it obvious

2
What pricing model do you prefer or want to avoid? (subscription, one-time, usage-based, freemium, hybrid)
Determines the entire structure
Pricing model already stated in context

3
What's the primary value metric that scales with usage? (seats, API calls, storage, projects, transactions, etc.)
Drives tier differentiation and upgrade logic
Product type + features make it obvious

4
Target gross margin range? (60-70%, 70-80%, 80%+, not sure)
Sets the floor for every price point
A number or range is already given

5
How price-sensitive is your target customer? (very sensitive, moderate, willing to pay premium)
Calibrates price positioning and tier gaps
Audience detail + industry norms make it clear

6
Who are your closest competitors and how do they price?
Market anchoring — prevents under or over pricing
Competitors section is filled

7
What's your current stage or revenue target? (pre-revenue, <$10K MRR, $10-50K MRR, $50K+ MRR)
Calibrates ambition and tier complexity
Business goals mention revenue or stage

Use AskUserQuestion to ask up to 4 questions per batch. Ask the highest-priority unanswered questions first. If the first batch gives you enough to build a confident strategy, stop. Maximum 7 questions total, but fewer is better — stop as soon as you can build a strong strategy with what you have.

3. Determine Strategy Type

Based on all collected inputs, decide the structure. Make this decision yourself — do not ask the user. Explain why in the output.

Condition
Strategy Type

Subscription + B2B
SaaS Tiered — Starter / Pro / Business / Enterprise

Subscription + B2C
Consumer Tiered — Free / Basic / Premium

Usage-based primary
Usage Tiers — base fee + usage bands with overage pricing

One-time purchase
Package Pricing — Good / Better / Best bundles

Freemium preferred
Freemium — generous free tier + 2-3 paid tiers

Mixed signals
Hybrid — combine structures as the inputs warrant

4. Build the Pricing Strategy

For each tier, define:

Plan name — descriptive, not generic. "Starter" beats "Plan A". "Growth" beats "Mid".

Price point — monthly AND annual (annual ≈ 20% off monthly). Use specific numbers.

Price justification — why this number. Anchor to: competitor benchmarks, value delivered, margin targets, or customer willingness to pay. Never leave a price unjustified.

Feature set — what's in, and critically, what's deliberately left out to drive upgrades.

Target segment — the specific customer who buys this tier and why.

5. Add the Strategic Layer

Beyond the tiers:

Positioning — where this sits vs. competitors (premium, mid-market, value leader, underdog)

Psychological tactics used — name them and explain why each one was chosen (charm pricing, anchoring, decoy effect, loss aversion in annual vs. monthly, etc.)

Upgrade triggers — what specifically moves a customer from tier N to tier N+1

Revenue optimization — annual discount incentives, add-ons, usage overages, upsell moments

Biggest pricing risk — one specific risk for this business and how to mitigate it

6. Format and Verify

Structure output per Output Format below

Run through Quality Checklist before presenting

Pricing Principles

Hard constraints. These exist because bad pricing destroys margins or kills growth.

Price on value delivered. Never on cost to build.

Every tier must have a clear reason to exist. If no real customer would buy it, cut it.

The middle tier is the hero. Design the strategy so most customers land there.

Annual pricing should feel like a no-brainer — 20-25% off. Monthly is the convenience premium.

Never show more than 4 tiers. Paradox of choice kills conversion at the pricing page.

Enterprise = "contact sales" unless the business is pre-revenue. Pre-revenue can skip Enterprise or price it transparently.

Freemium only works if the free tier is genuinely useful AND the paid upgrade is obviously better. A crippled free tier is worse than no free tier.

Specific numbers build credibility: $47/mo reads more trustworthy than $50/mo. Use this deliberately — not on every price point, but on the hero tier.

B2B + deal size above $200/mo → seat-based pricing is almost always correct.

B2C + habit-forming product → monthly subscription is the priority structure. Annual is secondary.

Price anchoring matters. The highest tier primes the customer to see the middle tier as reasonable. Design for that.

Output Format

## Pricing Strategy for [Company Name]

**Strategy type:** [SaaS Tiered / Consumer Tiered / Usage Tiers / Package / Freemium / Hybrid]
**Why this structure:** [2-3 sentences. Why this model, not another.]

---

### [Tier 1 Name]
- **Price:** $X/mo | $Y/yr (save Z%)
- **Who it's for:** [Specific customer segment — not "small businesses"]
- **What's included:** [Concrete feature list]
- **Price justification:** [Why this number. Anchored to what.]

### [Tier 2 Name]
- **Price:** $X/mo | $Y/yr (save Z%)
- **Who it's for:** [Specific segment]
- **What's included:** [Feature list — highlight what's new vs. Tier 1]
- **Price justification:** [Why this number]

### [Tier 3 Name]
[same structure]

---

### Positioning & Psychology
- **Market position:** [Where you sit vs. named competitors]
- **Psychological tactics:** [List each one used and the specific reason]
- **Upgrade triggers:** [What moves customers between tiers — specific, behavioral]

### Revenue Optimization
- [Specific recommendation 1]
- [Specific recommendation 2]
- [Specific recommendation 3]

### Biggest Pricing Risk
[One specific risk for this business. Not generic. How to see it coming and what to do.]

Quality Checklist (Self-Verification)

Pre-Execution Check

 I read FOUNDER_CONTEXT.md before asking any questions

 I only asked questions the context didn't already answer

 Total questions asked: 7 or fewer

Strategy Check

 Strategy type is justified (not a generic default)

 Each tier has a clear reason to exist

 Middle tier is the obvious "best value" — the hero

 Price points are anchored to competitors, value, or willingness to pay — not guessed

 Annual pricing is 20-25% below monthly

 4 tiers or fewer

Pricing Principles Compliance

 All prices are value-based

 Freemium tier (if present) is genuinely useful, not crippled

 B2B high-value products use seat-based logic where appropriate

 Psychological tactics are named and justified

Output Check

 Every tier has a price justification — none are bare numbers

 Positioning is specific to this business and its competitors

 Revenue optimization is actionable, not generic

 The "biggest risk" is specific to this business — not boilerplate

If ANY check fails → revise before presenting.

Defaults & Assumptions

Use these unless the user overrides:

Pricing model: Subscription (most common for modern products)

Tiers: 3 for most businesses. 4 only if B2B with a clear Enterprise segment.

Annual discount: 20%

Target gross margin: 75-80% (SaaS baseline; adjust for non-software)

Price sensitivity: Moderate (mid-market default)

Currency: USD

Billing cycle: Monthly with annual option

Document any assumptions made in the output.