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How aggressive should our upgrade prompts be for users approaching free plan limits?

Based on Price to Scale’s approach, upgrade prompts for free plan users nearing usage limits should be handled with a balanced, segmented, and context-sensitive strategy. Here are some key takeaways from our book:

• Maintain balance and subtlety: Rather than overwhelming users with aggressive upgrade prompts, aim for targeted messages that emphasize additional value. This helps avoid the risk of alienating customers or creating a negative user experience.

• Segment your user base: Recognize that free users nearing their limits may represent different types of customers. For example, some might be heavy users who realize the benefits of upgrading, while others might only need a temporary lift. Tailoring your prompt based on usage behavior and customer attributes ensures the messaging feels relevant and considerate.

• Provide creative alternatives: Instead of a blunt call-to-upgrade, consider offering alternatives such as a better option for the same price, a special discount, or an add-on that meets their specific needs. This proactive approach can make the upgrade feel like a natural, beneficial transition rather than an enforced escalation.

• Avoid cannibalization: Price to Scale warns against being overly pushy as aggressive prompts could convert into cancellations or deter existing upgrades. The goal is to foster trust and long-term engagement by clearly communicating the benefits without pressuring the user unduly.

In summary, when users approach free plan limits, upgrade prompts should be mindful and tailored—providing clear, attractive value propositions without being overly aggressive. This approach not only respects the customer journey but also optimizes the chances of a smooth, successful upgrade path.

Get Started with Pricing Strategy Consulting

Join companies like Zoom, DocuSign, and Twilio using our systematic pricing approach to increase revenue by 12-40% year-over-year.

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