Twenty-five years ago, the idea that a typical charitable gift annuity donor, perhaps a retired schoolteacher in her mid-seventies, would research CGA payout rates on a charity’s website before ever speaking to a gift officer would have seemed far-fetched. Yet today, it is not only common; it is expected. Donors arrive at conversations already informed, already partially educated, already knowing that ACGA rates are standardized across organizations. The internet did not replace the gift officer. It made the gift planning officer’s job more meaningful. Artificial intelligence is about to do the same thing, only faster, and at a moment when the opportunity to write more CGA contracts has never been greater in the history of planned giving.

A note before we begin: this article will not describe the general landscape of AI tools available today. I am going to assume that you, as a reader, have already developed some baseline familiarity with generative AI. If you have not, I would encourage you to seek out a reliable introductory resource, such as YouTube, and other platforms that offer excellent free training to walk you through the fundamentals and help you choose a platform for everyday personal use. I would also encourage you to review your organization’s AI policy before using any AI tool for work-related discussions or tasks.

History as Proof

When planned giving websites first emerged in the early 2000s, some gift officers worried they would be made redundant. If a donor could read about a charitable gift annuity online, why would they need to call? What actually happened was the opposite. Websites democratized access to basic planned giving education and filtered out early, exploratory questions, freeing gift officers to do what only they could do: build relationships, understand a donor’s values, determine which assets to fund the CGA with, and guide them through a deeply personal financial and philanthropic decision.

A planned giving job description today may look similar to one from twenty-five years ago. But how you spend your day is fundamentally different because of all the technological advancements driven by the internet over the past 25 years. Your productivity is higher. Your donor conversations are richer. The planned giving website did not diminish the gift officer. It elevated the work. 

AI will follow the same arc, only at a pace that will feel much faster.

The Next Evolution: From Static Web Pages to Intelligent Conversations

The website era gave donors static information: a page explaining what a CGA is, a basic calculator, and a PDF brochure to download. The AI era will give donors something far more powerful: a dynamic, personalized conversation available at any hour of the day or night.

Imagine a donor visiting your organization’s website at 10 PM on a Tuesday. Rather than reading a generic fact sheet, she interacts with an AI agent that asks a few simple questions about her age, the asset she is considering, and responds with an initial illustration far more personalized than what has been available. The agent then asks her if she’s ready to speak with one of the Gift Planning representatives at the organization, and there’s an email in your inbox the next morning from her, not as a prospect, but as a donor ready to discuss a CGA.

This is not science fiction. Donors in every other area of their financial lives, banking, investing, and insurance, are already interacting with AI tools that give them instant, personalized information. They will expect the same from the organizations they love. The AI agent takes the website a full generation further: from reading to conversation, from general to personal, from informative to actionable.

Building these tools responsibly requires careful attention to donor privacy and data security. Any AI application that engages donors in personalized conversations would likely involve PII, Personally Identifiable Information, and that demands rigorous information security standards from the ground up. But this is not a reason to hesitate. It is simply the cost of building something worthy of our donors' trust. The organizations that make that investment will be rewarded with tools that educate donors more effectively, create a better giving experience, and ultimately drive greater CGA volume, all while honoring the privacy of the people who make this work possible.

The Gift Planner’s Workstation: Democratizing Expertise

A second shift is underway, and it may be just as consequential as what is happening on the donor side of the table.

Through Planned Giving Interactive, we have built the Gift Planner’s Workstation: an AI-powered platform designed specifically for working gift planning practitioners. At its center is Frank™, an AI research copilot trained on a deep body of planned-giving knowledge compiled by some of the most experienced voices in the field. That expertise is now accessible in real time, on demand, for any member of your team.

What this enables is something the field has long needed: a genuine democratization of planned giving expertise. A newer member of your team, someone two or three years into the industry, can now get a well-grounded answer to a complex technical question in minutes rather than waiting for a senior colleague to be available (and many reading this in solo planned giving shops don’t have a senior colleague to learn from) to be available.  Frank™ delivers answers grounded in solid expertise, giving that practitioner the confidence to have a more substantive conversation with a donor right away.

This is not a replacement for experience or judgment. I always encourage practitioners to verify technical answers with a supervisor. But the objective of the Workstation is to raise the floor for the entire team. It gives everyone, regardless of where they are in their careers, the tools to be more responsive and agile, which is good for donors and the field.

The Relationship Remains the Differentiator

None of this changes the most important thing about planned giving: the relationship. Because ACGA rates are standardized, donors choose one organization over another not because of the rate but because of the trust they have built with someone on your team. That connection is something no AI tool can replace.

The gift officer who uses AI well will simply have more time for the one thing that actually drives CGA volume: being present with donors, earning their trust, and being there when they are ready to act.

The Greatest Opportunity in the History of Planned Giving

In 2026, the oldest Baby Boomers will be turning 80. The youngest is turning 62. That means the entire Boomer generation, nearly 80 million Americans, is now within the prime window for charitable gift annuity conversations. They are a generous generation. They have accumulated significant wealth. Many hold highly appreciated assets, stock, real estate, and business interests, that make CGAs extraordinarily attractive from a tax efficiency standpoint. And many are actively seeking ways to supplement their retirement income while honoring the causes they have supported throughout their lives.

We are not at the peak of the CGA market. We are at the very beginning of it.

AI tools are arriving at precisely the right moment, just as the largest demographic wave in American history enters the years when CGAs make the most sense. The Organizations who learns to adopt these tools now will be positioned to serve more donors, educate more prospects, and close more gifts than at any previous point in the history of planned giving.

A Final Thought

The gift officers who worried about planned giving websites in 2003 were not wrong to notice that change was coming. They were only wrong about what that change would mean for them. It did not diminish their role. It deepened it.

The same is true today. AI is not coming for your job. It is arriving in two forms at once: one that helps your donors become better educated and take action, and one that helps your team research and respond to donors and advisors faster. 

About the Author

Paul Caspersen, CFP®, MS, CAP®, AEP®, is an Assistant Professor at The American College of Financial Services and the Founder and President of Planned Giving Interactive, LLC (PGI), an A.I. planned giving software and advisory firm. Paul is also Vice President and advisor at Charitable Solutions, LLC, a national consulting firm that supports charities in accepting complex charitable gifts and developing charitable trusts.