Steps

Identify premium value moments

Map the moments in your product where users encounter premium features or hit free-tier limits. These are your conversion triggers — the points where users naturally think 'I wish I could do more.' Common triggers: usage limits, advanced features, team collaboration, and export capabilities.

Build contextual upgrade prompts

At each conversion trigger, show an in-app message explaining what the premium feature does and how it would benefit the user specifically. Use Escourtly to create targeted tooltips that appear when users hover over or click locked features.

Create a 'premium preview' tour

Build a product tour that showcases 3 premium features in context. Trigger this tour mid-trial (day 5 of a 14-day trial) when engagement is high. Show each feature actually working — not just a description, but a visual demo within the tour tooltip.

Design the trial-ending experience

3 days before trial end, trigger a summary tour: 'Here is what you have accomplished during your trial: [stats]. To keep access, upgrade now.' Personalize with their actual usage data if possible — number of tours created, users guided, etc.

Set up post-trial re-engagement

For users who do not convert, set up a degraded experience (read-only) rather than full lockout. Include an ever-present upgrade banner showing what they are missing. This keeps the door open for later conversion.

Variations

Usage-Based Conversion

Instead of a time-limited trial, trigger conversion prompts when users hit usage limits (e.g., 3 tours created, 100 users guided). This ties upgrade to value received.

Team-Expansion Conversion

Trigger upgrade flow when a user tries to invite teammates. Team features are natural conversion points — 'Invite your team? Upgrade to Team plan.'

Implementation Guide

Start by mapping your conversion triggers (Step 1). Most products have 3-5 natural moments where free users hit limits. Use Escourtly to create contextual tour steps at each trigger point. The mid-trial premium preview (Step 3) is the highest-impact intervention. Time it for when engagement data shows users are most active — typically day 4-7 of a 14-day trial. For the trial-ending experience (Step 4), personalization is key. 'You created 5 guides that have onboarded 47 users' is 10x more compelling than 'Your trial is ending.' Pull real usage data into the tour messaging. Measure free-to-paid conversion rate before and after implementing this flow. Also track which specific conversion trigger has the highest upgrade rate.

Frequently Asked Questions

When should I prompt users to upgrade?

At natural value moments, not arbitrary times. When a user hits a feature limit, tries an advanced feature, or achieves a milestone — these are moments where upgrade value is self-evident. Avoid prompting in the first 24 hours when users are still learning.

Should I lock features or show them grayed out?

Show premium features visibly but locked. Graying out with a 'Premium' badge lets users see what they are missing. Completely hiding features means users never know they exist, which removes a powerful conversion motivator.

What is a good trial-to-paid conversion rate?

Industry average is 2-5% for opt-in free trials and 15-25% for opt-out trials (credit card required). Well-optimized conversion flows push these higher. Focus on improving your own baseline rather than hitting benchmarks.

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