If a user’s free trial expires without converting, should we reach out with a special offer (like extending their trial or giving a one-time discount) to try to win them as a paying customer?

Based on our saas pricing book, Price to Scale, the answer is: Yes, you can reach out with a special offer—but it should be done thoughtfully and tailored to the customer segment.

Key points from Price to Scale:

• Tailor Your Outreach: Rather than offering a blanket extension or discount to every expired trial user, our book recommends segmenting your user base. This means targeting users who show potential for conversion with tailored offers that have clear value propositions.

• Be Strategic with Concessions: When making offers such as an extended trial or a one-time discount, ensure there’s a framework to justify the concession—such as asking for a longer contract commitment or bundling the offer with an upgrade or add-on. This avoids devaluing your product and helps you maintain a threshold for price positioning.

• Communication and Testing: The book emphasizes the importance of clear communication so that customers understand the continued value your product provides. Moreover, testing different offers in controlled segments (as discussed in our book) helps determine which incentives drive better conversion rates without undermining your overall pricing strategy.

In summary, while reaching out with a special offer post-trial expiration can be effective, it’s crucial to design these offers with segmentation and strategic terms in mind. This approach aligns with the methodologies in Price to Scale, ensuring your pricing strategy is both proactive and sustainable.