Pricing Architecture

Pricing is positioning. Every decision on your pricing page — the tier names, the price gaps, the feature gates, the presence or absence of a free tier — communicates something to a buyer who has not yet decided to trust you. "Starter / Professional / Enterprise" tells the buyer you started building for enterprises and added a cut-down tier for everyone else. "Monthly / Annual" with a 40% annual discount tells the buyer you're not confident they'll stay. Three tiers that all include your core feature tell the buyer you don't know what your core feature is worth. Paste this prompt into Claude or ChatGPT. Share your current pricing and deal/churn data. The AI names what each pricing decision is currently signaling, identifies the tier that's leaking, and prescribes a specific new architecture with tier names, price points, feature gates, and a free trial recommendation.

1. Click "Copy prompt" above and paste it into Claude or ChatGPT to start the session.
2. Share: current tier names and price points, what's included in each, who's buying each tier, where deals stall, which tier churns fastest, and your most successful customer profile.
3. The AI diagnoses what your current pricing communicates to a first-time buyer, identifies which tier is capturing wrong buyers or blocking right ones, and names the biggest pricing friction point.
4. You'll receive a recommended new tier structure with a table showing tier names, prices, who each is for, core features, and the feature gate that drives upgrade.
5. The AI makes one recommendation on free trial vs. freemium vs. demo-only — with a specific reason.
6. Use "fix my conversion" mode if you want to focus specifically on trial-to-paid conversion without redesigning the full architecture.

From a pricing diagnosis for a B2B project management tool ($49 / $149 / custom):

WHAT YOUR CURRENT PRICING SIGNALS:
"Starter at $49 is for people who can't afford Professional." The price gap signals scarcity, not segmentation. A buyer comparing Starter and Professional is being asked to pay 3x more for features they can't evaluate without a trial.

THE TIER THAT'S LEAKING:
Starter captures individual contributors who churn at 2.4x the rate of team leads. The ICP is a team lead, but the feature gate that would filter individuals (team members above 5) is in Professional. Remove it from the gate or add a team-size minimum to Starter.

RECOMMENDED TIER STRUCTURE:
| Tier | Price | Who It's For | The Gate |
|------|-------|-------------|---------|
| Team | $89/mo | Teams of 3–15 | Unlimited guests |
| Studio | $199/mo | Agencies, 15–50 seats | Client portals + white-label |
| Scale | Contact | Enterprise | SSO + audit log |

Tier naming rationale: "Team" and "Studio" communicate situation, not value hierarchy. Buyers self-select rather than defaulting to cheapest.
Free trial recommendation: 14-day full-feature trial, no credit card. Current demo-only approach delays the aha moment by 4–7 days.