AI-personalized upsell copy

Personalizing the pre-donation upsell message with AI did not increase recurring giving.

What we tested

The pre-donation upsell screen is one of the most important moments in Checkout. Before completing a one-time gift, donors are given the opportunity to turn their contribution into ongoing support.

Until now, this screen has used the same messaging across all organizations. We wanted to understand whether more tailored messaging could make the experience feel more relevant to donors and encourage more supporters to choose monthly giving.

To test this, we implement AI that carefully uses information about each participating nonprofit's mission, programs, and brand to generate personalized upsell messages. The donation flow, design, and calls-to-action remained unchanged — only the copy varied.

Two AI-generated approaches were tested:

Brand-focused copy: focused on the organization's brand and the value of ongoing support
Cause-focused copy: emphasized specific programs and projects supported by donations

The goal was to determine whether more relevant messaging could encourage more donors to choose monthly giving.

Hypothesis

If we personalize the pre-donation upsell copy by organization and cause, conversion to monthly support will increase by at least 5% without meaningfully reducing donation conversion, because more relevant messaging should feel more compelling and less generic to donors.

Test setup

Duration	36 days
Timing	January–March 2026
Audience	~108,000 visitors who reached the pre-donation upsell screen
Group split	• 33% control (existing upsell copy) • 33% AI personalized copy (brand-focused) • 33% AI personalized copy (cause-focused)
Key metrics	• Donation conversion rate • Conversion to monthly support • Upsell-to-donor conversion

Key results

The personalized messaging did not improve recurring giving and negatively impacted donation completion.

−4.15% decrease in conversion to monthly support for the brand-focused copy
−10.5% decrease in upsell-to-donor conversion for the brand-focused copy
−8.61% decrease in upsell-to-donor conversion for the cause-focused copy
−0.85% decrease in overall donation conversion for the cause-focused copy

Neither personalized variant produced a statistically significant improvement in recurring giving.

Conclusion

The hypothesis was not confirmed.

Personalizing the upsell message with AI did not increase recurring giving and reduced the number of donors who completed their donation after seeing the upsell.

While personalized messaging is often viewed as a best practice, this test demonstrates that more tailored copy does not automatically lead to better fundraising outcomes. In this case, the existing message continued to perform better.

What this means for you

AI is a powerful tool, but every application needs to prove its value with real donor behavior.

This test is a good example. While personalized messaging seemed promising in theory, the data showed that it failed to increase recurring giving. Rather than rolling it out, we kept the experience that performs best for donors.

More importantly, this reinforces our approach to optimization. We don't introduce new technology simply because it's innovative. We test every change against real fundraising outcomes and only ship what demonstrably helps nonprofits raise more.

Your Checkout continues to use the upsell experience that delivers the strongest results today, while we keep exploring new ways to grow recurring giving.

→ Explore how AI actually optimizes donor experience and brings in more revenue