Upgrade Prompt

This drill builds a system that identifies users approaching plan limits or demonstrating power-user behavior, then delivers contextual upgrade prompts that feel helpful rather than pushy.

Prerequisites

• PostHog tracking usage metrics per user and per account
• Clear plan differentiation (what features or limits differ between tiers)
• Intercom configured for in-app messaging
• Loops configured for triggered emails

Steps

1. Define upgrade triggers

Using the posthog-custom-events fundamental, identify the usage patterns that correlate with upgrade readiness:

• Limit proximity: User is at 80%+ of a plan limit (seats, storage, API calls, projects)
• Feature discovery: User tried a premium feature during a trial or repeatedly hit a feature gate
• Growth signals: Added 3+ team members in a month, usage volume doubled
• Power user behavior: Using advanced features, API access, or integrations that indicate sophistication
• Time-based: On free plan for 30+ days with consistent active usage

Each trigger should be validated against historical data: do users who hit this trigger actually upgrade at a higher rate?

2. Build the trigger detection

Using posthog-cohorts, create cohorts for each upgrade trigger. Set up a daily check (via n8n or PostHog actions) that identifies users entering these cohorts. Score urgency: limit proximity is urgent (they will hit the wall soon), while growth signals are opportunity-based (upgrade would help them do more).

3. Design contextual prompts

The upgrade message should be tied to the trigger, not generic. Using intercom-in-app-messages:

• Limit proximity: "You've used 45 of 50 projects. Upgrade to Pro for unlimited projects." Show when they are in the product, near the limit.
• Feature gate: "This feature is available on the Pro plan. Here's what you'll get." Show immediately when they hit the gate.
• Growth signal: "Your team is growing — Pro includes advanced permissions and team analytics." Show in a banner, not a blocking modal.

Always include: what they get, the price difference, and a one-click upgrade path.

4. Set up email nudges

Using loops-transactional, send upgrade emails for non-urgent triggers. Time them 24-48 hours after the trigger event (not immediately — give users time to experience the need). Include a personalized usage summary: "You've created 47 projects this month and invited 5 teammates — sounds like your team is getting value."

5. Route high-value accounts to sales

For accounts above a revenue threshold or with enterprise signals (large team, heavy API usage), do not self-serve the upgrade. Using attio-deals, create an expansion deal in Attio and assign it to the account owner. Include the usage data and trigger reason so sales can have an informed conversation.

6. Measure upgrade funnel

Track the full funnel: trigger fired, prompt shown, prompt clicked, upgrade started, upgrade completed. Calculate conversion rate by trigger type. A/B test prompt copy and placement. Aim for in-app upgrade prompts to convert at 5-10% for limit-proximity triggers.