PLG Upgrade Prompts

Put the paywall where a user has already got value and wants more, say plainly what upgrading gives them, and measure every prompt as its own funnel so you fix the one that is actually losing upgrades.

When to use

The user runs a freemium or free-trial product and wants more free users to pay: setting plan limits, placing upgrade prompts, writing prompt copy, or working out why free-to-paid is low. If users never reach first value, the problem is earlier: use onboarding-activation. If the tiers and price points themselves are in question, use pricing-and-packaging.

Before you start

1. Read the brand/product context first. Pull plans, pricing, ICP and buyer roles from .agents/product-marketing.md. If none exists, ask.
2. Get the activation moment (from onboarding-activation). Without it, you cannot tell a value moment from an annoyance.
3. List every limit, gate and prompt in the product today: what triggers it, who sees it, and where the click goes.
4. Get the counts per prompt for one period, as unique users: hit the limit, saw the prompt, clicked upgrade, and paid through that click. If they are not tracked, the first deliverable is the event plan below.

Method

Diagnose with the funnel behind each prompt. A prompt can fail at three stages: delivery (users hit the limit but never see the prompt), click (they see it and do not act), and checkout (they click and do not pay). Each stage has a different fix: a bug or frequency cap, the moment or the message, and the pricing or checkout flow. Compare prompts only against each other, with intervals, and rank them only where a significance test says they differ.