What is 'Rolling Retention'? Fundraisers Using AI and Better Metrics

Donor retention is not just a feel good metric it is one of the most powerful levers in the business model of a nonprofit. We sit down with Kirsten Wantland, Principal Industry Strategist at Bloomerang, to explore how organizations can move beyond fear and confusion and actually use retention data to protect revenue and grow lifetime value.

Kirsten begins by explaining her new role at Bloomerang, serving as a bridge between fundraisers in the field and the engineering and product teams. She brings frontline development experience directly into the CRM design process and is now helping shape Penny, Bloomerang’s new AI strategic fundraising partner. Penny will guide staff on which segments to work, what messages to send, and where to focus limited time so small teams can function like much larger shops.

From there, the conversation turns to why traditional retention tracking leaves so many nonprofits stuck. Measuring retention once a year on a calendar basis keeps leaders in a reactive posture, staring at last year’s results instead of managing today’s risks. Kirsten introduces the concept of ‘rolling retention’ a metric that constantly surfaces donors who are about to lapse based on their actual giving patterns. That simple shift creates a proactive pipeline of people to thank, call, invite, and re-engage before they disappear.

At the heart of her approach is a deeper philosophy about donor relationships. As Kirsten puts it, “Ultimately, our donors want a place to belong. They want to be part of a mission. They want to be part of a solution.” Rolling retention, better benchmarking, and even AI tools like Penny are there to serve that goal helping fundraisers step away from purely transactional requests and toward thoughtful, ongoing engagement.

Kirsten closes by urging organizations to start somewhere, choose a few key metrics, track them consistently, test new strategies each quarter, and adjust when the data shows no movement. In a crowded landscape of 1.8 million nonprofits, the ones who treat retention as a core business function not just an afterthought will be the ones that build resilient revenue and loyal communities.

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