Here's something you need to understand about AI: it's really good at answers. It can generate content, summarize transcripts, and produce data on demand. What it can't do is make someone feel something.
That gap between information and emotion is where sales professionals win or lose deals in 2026.
We brought together three people who understand this at a fundamental level: Sterrin Bird, Nonprofit Executive in Residence at Attain Partners, who's raised $5.5 billion through storytelling in the nonprofit world. Billy Draper, a distinguished strategic solution engineer at Salesforce, has spent two decades using stories to break through the noise across 30+ industries. And Alison Macalik, director of pre-sales at Ontic, empowers others to find their voice and share their authentic stories through her work with WISE, the Presales Collective, and her Imposter Talks podcast.
Their conversation revealed something critical: the same skills that close nonprofit gifts and enterprise deals are the ones AI will never replicate. Here's what matters.
Before diving in, we asked the audience what they struggle with most in sales. The options: getting attention, creating trust, getting buy-in, or being remembered.
Buy-in won by a significant margin.
Think about that. In a world drowning in data, features, and AI-generated content, the thing sales professionals struggle with most isn't capturing attention it's converting it into action. That's a storytelling problem, not an information problem.
Billy Draper can tell you the exact moment he understood the power of story in sales.
Fresh out of college, he had dreams of becoming a copywriter on Madison Avenue. Instead, he found himself in Birmingham, Alabama, working as a graphic designer at a utility company with a vision: make social media a legitimate business tool. This was when most organizations saw social media as frivolous—something for posting selfies, not managing risk.
Vendors came in to pitch solutions. Billy was vetting them, running through feature checklists like everyone does. Then he watched a guy named Justin McCauley sit at the end of the table and do something different.
"He told the story of the platform," Billy said. "Not the platform itself, but he made the solution the hero to our business. I was like, I want to be that guy."
When Billy got hired at Sprinklr, he went into his certification ready to prove he knew the technology. He click-mapped the entire platform, every screen, every feature. His manager stopped him cold.
"We didn't hire you to be the robot that knows every click," they said. "We hired you because of your passion for storytelling in your interview. You did what one of our best SEs already does, so do that."
That moment crystallized something Billy carries everywhere: always be a storyteller first and a technologist second.
Sterrin Bird had a different challenge. She was speaking to 75 bank executives about United Way at a downtown San Francisco luncheon. Picture it: executives filing in, grabbing burritos, mentally checking the box on their corporate engagement obligation. Knuckles dragging, as Sterrin put it.
She knew the data. She knew the stats about housing insecurity and poverty in the Bay Area. But data wasn't going to cut through the noise of people who didn't want to be there.
So she opened with this: "I am standing before you today as a 30-something-year-old single mom of two, and I am housing insecure."
The room shut up.
She was standing in front of them in a suit, well-dressed, clearly employed as a vice president of development. She didn't look housing insecure. But 62% of her take-home income was going to rent, which by definition made her exactly that.
"The reality of the Bay Area," she continued, "is that there are more people who look like me that are actually housing insecure than are not."
Then she showed the slide with the statistic.
Notice what happened there. She grounded the abstract concept in a personal story... the story of me. Then she connected it to the broader context... the story of us. Then she gave them the reason it mattered right now... the story of now.
This is the public narrative framework from Marshall Ganz at Harvard Kennedy School, and it works because it moves people from passive observers to active participants.
"Once I grounded it in that," Sterrin said, "they got it. I dropped that bomb saying, guess what? It's hard for me to pay my rent. And I'm standing in front of you advocating that we're asking all of you to help the many others like me that can't do it."
Here's where the conversation got uncomfortable in the best way.
Staryn shared research from Chris Ernst, chief learning officer at Workday, about how younger generations are using AI. They're using it constantly to generate content. But they're spending nearly 40% of their time correcting what was written.
There's a productivity tax on AI-generated content that nobody talks about. Not just the time spent fixing robotic language, but the cognitive cost of skipping the process of discernment—the thinking, debating, and shaping that happens when you actually write something yourself.
"For me, the process of writing is really about discernment," Sterrin said. "It's about really taking different pieces of information that I have and forming my own perspective or point of view on it."
That discernment is shaped by experience. And experience is what makes you authentic.
Billy jumped on this immediately. "Discernment is when you're debating and you're thinking. What shapes the authentic thing that's born out of that discernment, the story, whatever, is shaped by your experience. That is the human element."
AI can simulate empathy. It can generate content that sounds empathetic. But it can't experience anything. It can't discern based on 20 years of sitting across from buyers who are afraid of change, or donors who want to make an impact but don't know where to start.
That gap is your edge.
Most sales professionals make one critical mistake when they try to tell stories: they try to tell the entire story.
Billy's seen this hundreds of times. Someone gets excited about storytelling and decides to walk prospects through every possible scenario, every feature, every outcome. They eliminate all the white space.
"When you try and tell the whole story, you eliminate space for the customer to be part of the story," Billy said. "I purposely leave out pieces of a story because I'm trying to capture your curiosity. I want you to think about what I'm telling you and I want you to sit there for a minute."
Here's what happens when you do this right: when you build a solution together with the customer filling in gaps, they're now buying their own idea. They're leaning into their own story. They're offering, influencing, and directing it.
"That takes a little bit of courage," Billy said. "And vulnerability and experience. To say, don't tell the whole story, tell the right parts, leave parts out on purpose, and see what happens."
This is exactly what 2Win teaches with Moments That Matter. You don't walk through every click. You identify the moments that actually change how your prospect thinks about their business, then let them fill in the rest.
Alison asked both Billy and Sterrin about times when all the data supported a decision, but the buyer still said no—until a story changed everything.
Sterrin shared an example from the $5.5 billion she raised. She was working with enterprise-level nonprofits that had millions of prospects in their databases. Traditional fundraising consultants would charge $150,000 for feasibility studies that essentially said, "You have 100,000 people on your file capable of giving X amount."
The data was there. The capability was there. But organizations weren't acting on it.
"My ability to tell that story to those enterprise level fundraisers and say, I have done what you are doing and how you're doing it right now, which is hard and it is ripe with human error—that was the difference maker in making that sale."
She didn't lead with the technology. She led with shared experience. She named the pain: trying to find needles in haystacks, dealing with disjointed data, not even having a 360 view of donors, let alone knowing where they're entering or leaving the funnel.
Then she connected it to what was possible: automation and AI handling the analytical work while humans focused on the relationship work; the actual fundraising.
"The trust was built through the shared lived experience," Sterrin said.
Billy added the critical piece that comes next: "The story got people leaning in. Emotionally, you have now connected. You've done the credibility thing. Ultimately, we had to do some of the more logical work on the back end of that, because we had to build a business case. You have to blend those two."
The pattern is consistent: story creates the emotional opening, data provides the logical proof, and together they stretch the buyer's ambition to see what's possible.
Afraid of making the wrong choice. Afraid of the change your solution requires. Afraid of what happens if it doesn't work. In the nonprofit world, where Sterrin spent most of her career, this fear is amplified because the margins are thin and you're dealing with people's lives.
"The opportunity to create a shared set of values and vision and to share 'I've been in your shoes, I know this is scary' that's actually part of the unintended consequence of selling with storytelling," Staryn said. "People feel seen and held for their fears as well as their aspirations."
Most sales professionals are taught never to call the baby ugly. But addressing fears directly, naming them, validating them, showing you understand them, is often what creates the trust that leads to buy-in.
Sterrin's origin story in fundraising is a perfect example. She grew up in a family that was very philanthropic. Her parents also died homeless.
"I've spent my entire life understanding what it was like to be able to give and also having to internalize the courage it takes to ask for help."
That vulnerability that authentic understanding of both sides of the transaction is what makes her storytelling credible. She's not performing expertise. She's sharing experience.
Billy made a point that should fundamentally change how you think about sales conversations: "A good story should create conversation. It's not how to sell to somebody through a story, it's how to tell the story to have the conversation so that you can come to the right conclusion together."
This reframes everything.
You're not using stories to manipulate buyers into saying yes. You're using stories to create the conditions for honest dialogue about whether your solution actually solves their problem.
"The job of a really good fundraiser," Sterrin said, "is to make sure the person you're sitting across from has all the information about the mission, the vision, what you're trying to do so that they can make the best decision for themselves."
The same is true in sales. As long as you've given your customer all the information they need in a human and authentic way, they will make the best decision for themselves. That's how this works.
And here's the kicker: when they make that decision (even if it's no) they trust you more than they would have if you'd tried to manipulate them with data-heavy feature tours.
The conversation took a sobering turn when Sterrin talked about teaching her son how to leave a voicemail.
"He's no fool. He's a great kid. But he's like, what? I was like, when it beeps, I want you to say, hi, it's Tommy Gooch, and follow up."
This isn't about voicemails specifically. It's about a generation growing up with instant gratification from social media and AI tools that can generate anything on demand. They're losing the muscle memory of human interaction, discernment, and the time it takes to develop expertise.
"There's a disconnect," Staryn said, "between what hard work and what time it takes to do this work, any work, versus what we're being fed because it seems like it's all instant. And it's not instant."
Billy connected this to the broader challenge: "We live in an answer economy. It used to be that people would read the news, but instead they're going to query the news now. So it's even more transactional. Give me the answer and I don't need to actually do the thoughtful stuff, the discernment, the shaping and forming of my own opinions."
The risk isn't just that younger salespeople won't know how to tell stories. It's that they won't understand why stories matter—because they've never experienced the alternative.
Alison asked the final question: if we don't get better at storytelling, if we lose this in the AI world, what's at stake for sales?
Staryn's answer cut deep: "We're watching it in real time. We're watching the expression 'divide and conquer.' Everything is an echo chamber as a result of this and dialogue is going away. That's where creativity goes to die."
When you lose the ability to tell stories, to connect through shared experience, to create space for authentic dialogue, you lose the ability to work together. In teams. With customers. In communities.
Billy brought it back to sales: "You quickly become irrelevant. You lose your agency. You lose the ability to share your experience and your expertise. Everything's a transaction. And I don't think that's good for anybody in the world of sales."
Transactions are quick. They're a moment in time. But if you're trying to build relationships that lead to long-term partnerships, renewals, and expansion revenue, you need something more.
You need stories that help buyers see themselves in a different future.
If you're thinking this all sounds great but abstract, here's the structure both Sterrin and Billy use:
The story of me: Who are you? Why do you care? What's your experience that makes you uniquely positioned to help?
The story of us: How does your experience connect to their situation? What shared values or challenges do you have?
The story of now: Why does this matter right now? What's the urgency or opportunity?
This isn't theoretical. Marshall Ganz developed this framework for public narrative at Harvard Kennedy School, and it works because it moves people from "that's interesting" to "this matters to me" to "I need to act."
Sterrin calls her version the Wingspan Method; passion, personality, purpose, and proposition. It's the same idea: start with why you care, connect it to who you are, link it to what matters to them, and only then present what you're proposing.
Here's your takeaway: AI can give you information faster than you can process it. It can generate content, summarize meetings, and provide answers on demand.
What it can't do is discern. It can't share experience. It can't make people feel seen, understood, or inspired to change.
That's your job.
Before your next demo, discovery call, or executive presentation, ask yourself:
What's the story of me that establishes credibility here?
What's the story of us that creates connection?
What's the story of now that drives urgency?
Don't try to tell the whole story. Tell the moments that matter and leave space for your buyer to fill in the gaps with their own vision.
Be vulnerable enough to name the fears alongside the aspirations. Be authentic enough that buyers trust you're not just performing expertise.
And remember what Billy said about his mentor Chuck Geiss: never fall in love with your ideas. Be open to feedback. Let the story evolve through dialogue.
Because in 2026, with AI handling the transactional work, your ability to connect through story isn't just a nice-to-have skill.
It's the only sustainable competitive advantage you have left.