Return on investment doesn't always arrive in a spreadsheet. Sometimes it walks up to you at dinner. Sometimes it shows up as a percentage drop in call volume. Sometimes it's the moment a vendor finally understands what you've been asking for all along.
Association boards want proof that AI investments pay off, and they're right to ask. But the proof comes in different shapes.
At digitalNow 2025 in Chicago, hundreds of association leaders gathered to compare notes between sessions, over lunch, in hallway conversations that stretched past scheduled breaks. What became clear: associations aren't talking about AI plans anymore. They're comparing outcomes. The question shifted from "should we do this?" to "here's what happened when we did."
These are real conversations with association leaders sharing what actually happened when they implemented AI tools, trained their staff, and measured the results that mattered to their organizations.
David Dellin arrived at digitalNow with data. As the leader of the American Paint Horse Association, he oversees an organization with 40,000 members worldwide and 42 employees. Sixteen of those employees work in member care, answering questions while simultaneously processing registrations, memberships, and paperwork.
The challenge Dave faced was geography and time. When a member in Fort Worth needs an answer at 2 AM, nobody's in the office. The association's website contains extensive information, including detailed rule books, but navigating it requires knowing where to look. Members were calling with questions that staff had answered hundreds of times before.
In November 2023, the Paint Horse Association implemented an AI knowledge assistant (powered by Betty). The tool can answer rule questions that previously only member care staff could handle, drawing from the association's extensive documentation.
The result? A 30% reduction in phone calls.
That number represents more than efficiency:
Dave has been running this tool for over a year. This isn't a flash-in-the-pan result from an enthusiastic first month. The data holds. When you give members 24/7 access to answers, they use it. When you track the impact over twelve months, the pattern becomes clear.
Bruce Moe accepted an innovation award at digitalNow 2025 for the work his team has done at the Missouri State Teachers Association. When asked about ROI, Bruce was honest: "I don't know that we've measured it that way."
What he does have are stories. The kind that matter.
A few months ago, Bruce attended a dinner with members. One teacher approached him specifically to share feedback about Tilly, Missouri State Teachers Association's AI knowledge assistant.
"I just want you to know," she told him, "that I am infatuated with Tilly."
She was redoing her entire curriculum using Tilly to generate ideas. Not replacing her expertise, not automating her judgment, but partnering with a tool that could help her think through possibilities faster than working alone.
This member sought Bruce out at dinner. Nobody sent her a survey. She wasn't responding to a feedback request. She wanted to tell him how much value she was getting from something his association built.
The ripple effect extends beyond Missouri. The Association of Texas Professional Educators launched their own version of an AI knowledge assistant this spring, seeing similarly positive results. Teachers across state lines are finding value in tools that help them do their work better.
How do you measure member satisfaction when it shows up at dinner instead of in surveys? How do you quantify "infatuated"?
Bruce's answer: you listen. You notice when members volunteer enthusiasm. You track adoption patterns and watch what happens when people choose to use something because it genuinely helps them.
Missouri State Teachers Association has been running Tilly for over a year. The tool has staying power because teachers keep coming back to it.
George Boyle walked into digitalNow 2025 with a clear challenge: the Illinois CPA Society serves members across a wide age range with varying comfort levels around AI. Some staff members were already experimenting with tools. Others worried openly about what AI meant for their jobs.
The organization made a strategic decision: invest in foundational training for everyone.
The Illinois CPA Society required all staff to complete three introductory courses through Sidecar's AI Learning Hub. The specific provider matters less than the principle: everyone needed to start from the same baseline before exploring individual applications.
The goal wasn't making everyone an AI expert overnight. The goal was building shared vocabulary and understanding. When staff members hear "AI can augment what they do rather than replace what they do," they need context to believe it.
This connects directly to a point John Huisman made during his digitalNow keynote session: 70% of successful technology implementation is about people and processes, not the technology itself.
You can't measure ROI on tools your team doesn't understand or trust.
The Illinois CPA Society's approach acknowledges that staff adoption rates matter as much as member adoption rates:
Illinois CPA Society is still in the foundation-building phase. George isn't reporting dramatic efficiency gains yet. What he's building is readiness. When the organization identifies the right AI applications for their specific needs, the staff will be prepared to implement them effectively.
Whether you build training internally, use external resources, or combine both approaches, you need a strategy for bringing people along. The Illinois CPA Society chose systematic education as the first step toward future ROI.
Matt Appenzeller came to digitalNow 2025 at a crossroads. As CEO of the Southern Ohio Chamber Alliance, he's developing products for chambers of commerce. He knew AI agents could maximize engagement with those products, but he kept running into the same wall: asking vendors "who can do this for me?" and getting vague answers.
Then Amith Nagarajan showed a single slide during his presentation. The slide demonstrated how a hospital association had aggregated data across its network.
Matt's immediate reaction: "That one slide was worth the price of admission."
He suddenly saw a pathway. Not a complete solution, not a vendor recommendation, but a clear picture of what was possible. The Southern Ohio Chamber Alliance could become the organization that does this kind of data aggregation for chambers across the United States.
Within hours of seeing that slide, Matt already had leads from vendors who could help execute the vision. The slide didn't solve his problem, but it gave him the language and framework to articulate what he needed.
This represents a different kind of ROI: strategic clarity. Matt didn't implement anything. He didn't measure efficiency gains. He got the answer to "is this even possible?" and shifted immediately to "here's how we'll do it."
Conference ROI doesn't always show up in immediate implementation. Sometimes it shows up in the shift from confused exploration to focused execution.
Matt's advice to other association leaders echoes this: "Just keep taking the next step. You're not going to digest it all at once."
The journey from "we need to do something with AI" to "we have a specific plan" often requires that one moment of clarity. For Matt, it was a single slide showing what another association had already accomplished.
>> If you want to see the slide Matt's referring, we will be adding the digitalNow 2025 keynote sessions to our AI Learning Hub within the next few weeks!
Look at the timeline across these stories:
None of them rushed. None of them expected overnight transformation. They all committed to a process and gave it time to show results.
These stories reveal a pattern. Associations are finding success by measuring what matters to their specific stakeholders, not chasing a universal ROI formula. The returns show up in three distinct ways, each valuable depending on what your organization needs to prove.
Operational efficiency: Paint Horse Association's 30% reduction in phone calls freed up staff to focus on work that requires human expertise. The numbers are clear, trackable, and sustained over twelve months.
Member value: Missouri State Teachers Association's teacher using Tilly to redo her curriculum represents ROI that doesn't fit neatly in a dashboard. Member enthusiasm, unprompted feedback, and voluntary adoption signal value in ways that matter deeply to association leadership.
Strategic clarity: Southern Ohio Chamber Alliance's shift from confused exploration to focused planning shows how understanding what's possible creates its own return. Knowing what to build is the first step toward building it effectively.
Your board will ask what matters to them. Your members will demonstrate what matters to them. Your staff will reveal what matters to them through adoption patterns and feedback.
The measurement question isn't "what's the ROI of AI?"
The measurement question is "what matters to our organization, and how will we know if we're succeeding?"
Not all ROI shows up in dashboards. Sometimes it shows up at dinner. Sometimes it shows up in phone logs. Sometimes it shows up in the clarity that finally lets you move forward with confidence.
Build the foundation first. Invest in training. Give implementations time to prove themselves. Track what matters to your stakeholders. The associations at digitalNow 2025 proved that when you do these things consistently, the proof arrives in multiple forms.
What you measure depends on what you need to prove. Some boards need hard numbers. Some members show value through voluntary adoption. Some strategic decisions require clarity before implementation.
Pick the metric that matches your stakeholders, then build your approach around proving that specific return.