Pricing Tier and Packaging Diagnosis
Finds why your pricing tiers underperform and redesigns value metric, fences, price gaps, and upgrade triggers with a migration plan.
Before & after
Same prompt, same agent — the only difference is the skill.
Freemium is a popular model for developer tools because it lets people try before committing. The key decisions are how much free tier you offer, when to paywall features, and how aggressively to upsell without frustrating free users. You'll want to think about unit economics — how much it costs to serve a free user, and what conversion rate you need from free to paid to be sustainable. Different pricing models work for different tools. You might consider per-seat, usage-based, or feature-based paywalls. I'd recommend looking at what similar tools charge and surveying your user base about willingness to pay. What features would be worth paying for in your space?
FREEMIUM PRICING SCENARIOS (Illustrative numbers; not financial advice.) SCENARIO A: Feature-Based Freemium Free tier: 1 project, 5 API calls/day, core features Pro tier: 50 projects, unlimited API calls, advanced features — $29/mo (annual: $290) Expected metrics: 2% free-to-paid conversion, 40% churn Unit economics: Free user costs $0.03/month to serve; Pro revenue covers 150 free users SCENARIO B: Usage-Based Model Free tier: first 1,000 API calls/month Paid: $0.05 per API call above 1,000 (capped at $99/mo tier for budget caps) Expected metrics: 5% free-to-paid conversion, 20% churn (users get value before paywall) Unit economics: Higher ceiling for power users; no seat limits SCENARIO C: Hybrid (Feature + Usage) Free: core features, 1,000 calls/month Starter: $19/mo, 10,000 calls, email support Pro: $79/mo, 100k calls, priority support, SSO Expected metrics: 3% free-to-paid, 25% churn, higher average revenue per user (ARPU) COMPARISON TABLE: A captures pricing-sensitive users; low revenue per user B scales with customer success; no feature gatekeeping frustration C balances expansion revenue with simplicity RECOMMENDATION: Start Scenario A; track free-to-paid conversion at month 3. If below 1.5%, migrate to Scenario B.
About this skill
"Nobody buys the middle tier." "Everyone sits on the free plan forever." "Sales discounts every deal by 30%." These are usually packaging defects rather than price-level problems, and changing the number on the page won't fix them. This skill works out which defect you have and redesigns the tiers around it.
What it does
- Tests your value metric: does the bill grow when the customer gets more value, and is it predictable for the buyer?
- Audits each tier for a nameable buyer, a fence that matches willingness to pay, and an upgrade trigger successful customers actually hit
- Checks the price gaps between adjacent tiers for cannibalization (too close) and cliffs (too far)
- Reads the signals you have, like tier mix, discount rates, limit-hit rates, and downgrade flows, and says what each one implies
- Floor-checks prices against variable costs, which matters for AI and usage-heavy features
- Produces a migration plan for existing customers: grandfathering, notice, and the order of changes
What you get
A diagnosis naming the specific packaging problem, a revised tier table (buyer, price, fence, limit, upgrade trigger), a migration plan, and the cheapest way to validate the change before you commit.
Best for
SaaS and digital-product founders, PMs, and growth leads whose tiers convert badly, whose customers bunch in the wrong plan, or who are launching tiers and want the packaging right the first time.
SKILL.md preview
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name: pricing-tier-packaging-diagnosis
description: Diagnoses and redesigns pricing tiers and packaging. It tests the value metric, each tier's buyer, fences, price gaps, upgrade triggers, and cost floors, then delivers a revised tier table and a migration plan. Use when the user says "nobody buys our middle tier", "review our pricing page", "what should go in Pro vs Business", "everyone stays on the free plan", "we discount every deal", "should we charge per seat or per usage", "help me design tiers for launch", or "our pricing feels wrong but I can't say why".
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# Pricing Tier and Packaging Diagnosis
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