Maddie Bell - Co-Founder and CEO of Scheduler AI: Driving Habit Change, Using Your Own Product, and Big Idea Thinking

Maddie Bell 00:00
Big ideas start with mind and heart-opening insights, and they actually have to be both. A mind and heart-opening insight is not an obvious statement of fact. It is something that lives just below the surface—something that’s there and people instantly recognize but didn’t realize was there before. When they realize it, it’s like, "Ah, that is true," right? That opens the mind. Then you can create this heart-opening piece of, "Now we can fix it. Now we can change it. Now we can paint a new picture."

Callan Harrington 00:34
You’re listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out the key items that led to their success. I’m your host, Callan Harrington, founder of Flashgrowth, and I couldn’t be more excited that you’re here. Welcome back, everyone, to another episode of That Worked! This week, I’m joined by Maddie Bell. Maddie is the co-founder and CEO of Scheduler AI, an AI appointment center that integrates directly into your CRM, web forms, and chats to coordinate meeting times in seconds while safeguarding your show rates. Prior to Scheduler AI, Maddie was a Brand Director for Procter & Gamble. While at P&G, she spent 12 years leading and delivering top-line, bottom-line, and share growth for multiple billion-dollar brands and products. The first thing that would jump out to you is Maddie’s energy. I’ve got to tell you, it’s hard not to be motivated when listening to her tell her story. We hit on a number of really interesting topics. She walked us through her process of measuring a potentially great idea to determine if there’s a market for it to become an actual business. In her words, “Just because something is innovative doesn’t mean that it’s valuable.” We also discussed the challenges of any product that requires a habit change from customers. With that, she walked us through her research strategy of understanding how customer behavior differs from the theoretical applications of AI. So Maddie, as I understand it, Scheduler was not your first startup, and there was a startup that was out there—not on LinkedIn or anything else. What’s the story on that?

Maddie Bell 03:24
I actually went to Duke University. For people that might know, Duke is pretty famous for the Cameron Crazies. They’re called “Crazies” because they’re basketball fans that do crazy things to attend games. Because the stadium is really, really small, not everyone can go. My freshman year of college, we actually slept in a tent for three months and three days to attend one Duke-UNC basketball game. We were the second tent in line of 100 tents to get in, so we were front row center.

I loved being at the game, but I realized, "There has to be a better way to get into one of the most coveted basketball arenas in the country." I learned that at the time, the university had a cable broadcasting network. It was a TV thing, and I decided we needed a multimedia broadcasting website. So, I started Duke Student Broadcasting. Guess who got to get the press passes for the basketball games? Me. I actually got to go to all the games, sit on the front row in press row, and interview the players after the game. That’s how Duke Student Broadcasting was born—and it’s all because I no longer wanted to sleep in a tent to get good seats to the game.

Callan Harrington 05:00
I love that it took three months in a tent to say, "Wait a minute. This isn’t right."

Maddie Bell 05:05
In fairness, I only solved the problem for me. There were still other people that had to go sleep in the tent. At the time, it was a bit more self-serving.

Callan Harrington 05:15
That was literally going to be my next question—was this a problem that just was solved for you for a press pass?

Maddie Bell 05:20
Which, yeah. I’m a die-hard Ohio State fan. That would have been amazing to get a press pass—it would have been the Holy Grail. Believe it or not, it led to an appearance on SportsCenter. I reported for ESPN and SportsCenter. Yes, it was a very high ROI. We did well, but we got to start a whole new, at-the-time, brand of ways of consuming student media and student stories. We were actually able to elevate the visibility of women’s sports, of other activities and groups on campus through that. I was passionate about it from all ends, but yes, that one perk was still pretty cool.

Callan Harrington 06:00
So one of the things I’m curious about is it looks like you were heavily involved within the entrepreneur community at Duke, and then you went to Procter & Gamble. Why go the big company route as opposed to joining a startup?

Maddie Bell 06:10
That story is a story in and of itself. When it was job season, it wasn’t even as easy as, like, “Oh, I want to go join a startup” or “Oh, I want to join a big company.” Because, as you probably recall, when you’re 22, you barely know what a job is. So, I think part of it was I was really setting out into the business world, and I had no idea what I was trying to do.

Believe it or not, just to date this, it was 2011. At the time, Google was still in its infancy, really. I applied and got accepted to work at Google. I was actually looking at apartments in San Francisco. What ended up happening was that the same professor who had helped me start Duke Student Broadcasting had spent 25 years at P&G, and they had decided that they were going to experiment with bringing undergraduates into what had typically been an MBA brand management position. He came to me and said, “Hey, have you heard of P&G? They’re coming, and I need you to dress up in a business suit and walk over to the MBA school because they’re going to interview some undergrads and see if you guys could be a fit.” So, I got interviewed, and they actually asked me about starting the broadcasting website.

What was really interesting was when they started talking about how P&G actually invented the product manager role. P&G has also produced more CEOs than any other company because it really teaches the foundations of business leadership. And then what blew my mind was they said, “When you come in, you’re given a part of a business to learn how to own and manage across every aspect: P&L, design, finance, R&D. We’re training you to run businesses at scale.”

Callan Harrington 07:45
That sounds like a tough choice!

Maddie Bell 07:47
Exactly. I had a choice: Do I go with Google, which at the time was the hottest company, the fastest, most technologically advanced with lava lamps at the Googleplex, or do I go with this 100-year-old soap company with giant towers and 100-year-old principles? After thinking about it, I decided I wanted to learn how to run a business. I even convinced my co-founder—who thought we were going to Silicon Valley—that Cincinnati, Ohio, could be a thing. To his credit, we’ve been together almost 20 years as co-founders in life and business. He said, “I see how that could change your life. You should do it.”

A couple of months later, he found out that the GE Edison program would pay for his master’s degree, and that’s how we ended up in Cincinnati. What I thought was really cool about my experience at P&G was that at each level, you’re owning your own part of a business. With that comes challenges that require innovative thinking and a deep understanding of the fundamentals of how businesses operate. Once you get those fundamentals, you can leverage them in a lot of different ways—whether in bigger businesses or, as Mike and I have done, by setting out on your own.

Callan Harrington 09:00
No question. There are very big differences between both scenarios, but there are also similarities. You’ve spoken very highly about your time at P&G, and one of the things you’ve mentioned is how you learned “Big Idea” thinking there. Can you give us an example of what that means and how it’s rolled out?

Maddie Bell 09:15
Yeah, as with all things in big companies, we actually had frameworks on frameworks for identifying a big idea. But really, it boils down to this concept that big ideas start with mind and heart-opening insights. They’re not obvious statements of fact. They’re something that’s just below the surface—something that, when people hear it, they instantly recognize as true but didn’t realize before. That’s the “mind-opening” part. Then, you create the “heart-opening” piece, where people feel, “Now we can fix it. Now we can change it. Now we can paint a new picture.”

At P&G, we measured ideas on whether they inspired amplification. Could this little idea grow into a big thing? Was it simple enough for enough people to immediately connect with it and see how it relates to them? For example, when you’re working on something as fundamental as soap, you have to figure out how to make people feel something about soap. Early on in my career, someone told me, “If you can inspire habit change in how somebody chooses their shampoo, you can do it with almost any product.”

Callan Harrington 10:30
How did you bring that same “Big Idea” thinking to Scheduler AI? It sounds like Scheduler came from a very distinct problem you were having, almost like the same process you described. Can you walk us through that?

Maddie Bell 10:45
Yeah, so our insight came at a point of tension—a very human tension. At the time, Mike was the VP of Data Engineering and Machine Learning for Nielsen, and I was running a billion-dollar brand for P&G. We also had two kids with a third on the way. Life was exactly what you’d expect with two high-demand jobs and multiple kids. The “lightning in a bottle” moment happened when we were leaving church one Sunday. We ran into some friends we loved and said those fateful words, “We should totally get together.” The problem was, we had said those words three Sundays in a row. By the time we sat in the car, I looked at Mike and said, “Scheduling is like solving a calculus equation every single time.”

That’s when it clicked. Scheduling doesn’t start with a calendar—it starts with a conversation and context. You should just be able to say, “I want to meet with these people,” and something somewhere should handle it. Wouldn’t that be great? Mike started seeing the problem everywhere—at work, at home, and with appointments. That’s where true innovation and big ideas come to life. It was clear this was a big idea, and that’s how Scheduler was born.

Callan Harrington 12:15
What were some of the initial roadblocks you ran into as you went through this process? What did you learn as you moved into different markets?

Maddie Bell 12:25
A lot of people—including us—believe that if you are an innovator, you are, by definition, an entrepreneur. Those two things are not the same. There are incredible entrepreneurs who weren’t necessarily innovators in the sense of bringing completely new technology to life. They were brilliant entrepreneurs who found a market, identified a problem, and served a need better than anyone else. And they got rewarded for it. That’s the game.

We started with a technical innovation that needed a market. It’s a very different path. Just because it’s an innovation doesn’t mean it’s a profitable, sustainable, scalable business. When we started digging, we asked, “How do we create a scenario where this innovation delivers real value to customers in a real marketplace?” Meetings happen everywhere, but there are different types: internal, external, one-on-ones, large groups, and recurring vs. one-offs. What we found is that within work, there’s one calendar that dominates 99% of homes: the work calendar. Within that, the blueprint of business growth comes from external meetings tied to revenue, recruiting, or talent acquisition.

Callan Harrington 14:10
How did that lead to shaping Scheduler into what it is today?

Maddie Bell 14:15
We started to identify that these growth meetings—external, large-scale—are critical for connecting people inside a company with buyers, prospects, or applicants. They require proactive scheduling. From there, we asked: How do we screen and qualify participants? How do we route them to the right person? How do we manage reminders and rescheduling? We drilled deeper into those specific needs, and that’s where AI came in. We realized the theoretical applications of AI didn’t always match how users adopt it. It wasn’t just about co-pilots that assist—it was about creating tools that could work autonomously without requiring users to change their habits significantly.

Callan Harrington 16:30
That’s fascinating. The sales tech and revenue tech space is competitive. How did you differentiate Scheduler from others in the market?

Maddie Bell 16:40
We stayed true to the insight: Scheduling starts with conversations, not calendars. Most incumbents focused on booking links, but we realized booking links just shift the problem onto someone else. With Scheduler, we used conversational scheduling to make it feel mutual and proactive. Instead of requiring habit change, we focused on value-first experiences. For example, Scheduler reschedules meetings autonomously, even responding to Sunday night changes for Monday morning calls. That kind of autonomy shifted perceptions and helped us differentiate.

Callan Harrington 18:50
For new clients who might not immediately see the difference, how do you convey that value?

Maddie Bell 19:00
One of the best decisions we made was to eat what we cook. If Scheduler couldn’t grow our business, how could we sell it to grow someone else’s? We fully immersed ourselves in the B2B SaaS go-to-market space to understand our customers’ pain points and refine our product. This meant integrating Scheduler into every part of our workflow—from generating leads to booking demos. We also embraced a multi-channel approach, incorporating email, LinkedIn, and even cold calls to showcase the value of AI-driven scheduling.

Callan Harrington 21:15
You’ve had great success so far. What’s next for you personally? How do you continue to evolve as a co-founder and CEO?

Maddie Bell 21:30
It’s about giving yourself permission to learn and start at the bottom again. My co-founder Mike exemplifies this. Despite being a VP at a top analytics company, he spent six hours cold-calling to better understand our customers and refine our approach. It takes courage to leave a room where you’re the expert and enter one where you’re starting fresh. But that’s where true growth happens.

Callan Harrington 23:15
If you could go back and give your younger self advice, what would it be?

Maddie Bell 23:20
It’s not the trophies on display that matter most. It’s the journey, the people, and the moments that shape you. Focus on building a life that integrates your passions, your family, and your purpose.

Maddie Bell 23:45
I’d also tell myself to let my world expand. When I was younger, my career was everything, and that’s great. It inspired me, drove me, and gave me purpose. But when I had my first child, my perspective shifted. Suddenly, I realized my passions and purpose could include more than just my work. Balancing work and family isn’t easy. There’s this constant push and pull—if I focus too much on one, I feel like I’m losing ground on the other. But the truth is, they don’t have to compete. They can complement each other if you approach it intentionally.

Callan Harrington 24:30
That’s such a great perspective. Did you struggle with that balance when you became a mom?

Maddie Bell 24:40
Absolutely. I think most working parents do, honestly. You’re trying to do everything at 100%—work, family, life—and it can feel impossible. Early in my career, I had incredible female mentors who helped me figure it out. One story stands out. I was working for a senior leader at P&G who was exceptional. She had this incredible ability to balance her career and family, and I looked up to her so much. When I found out I was pregnant, I was so nervous to tell her. We were traveling for work, and at 6 a.m. in the hotel gym, I told her. The first words out of her mouth were, “That’s the most incredible thing I’ll hear all week. What can I do to support you?” She helped me realize something profound: “You’ll never be the businesswoman you want to be until you can be the mom you want to be.” That advice stuck with me, and it’s shaped how I’ve approached my career ever since.

Callan Harrington 25:55
That’s such a powerful mindset. Do you think it’s something more leaders should emphasize?

Maddie Bell 26:00
Absolutely. Leaders need to create environments where people can bring their whole selves to work. That doesn’t mean sacrificing performance or results. It means recognizing that we’re all humans with lives and responsibilities outside of work.

When leaders create space for people to balance their lives, those people tend to bring their best selves to work. It’s a win-win.

Callan Harrington 26:30
I couldn’t agree more. Maddie, thank you so much for sharing your story. Before we wrap up, is there anything else you’d like to share with our audience?

Maddie Bell 26:40
I’d just say this: If you’re building something—whether it’s a company, a career, or a family—be intentional. Know your priorities, and don’t be afraid to pivot when those priorities shift. It’s okay to change direction if it means you’re building something that truly matters to you.

Callan Harrington 27:00
That’s such great advice. Maddie, thank you again for joining me on the show.

Maddie Bell 27:05
Thank you, Callan. This was a lot of fun.

Callan Harrington 27:10
I hope you all enjoyed my conversation with Maddie as much as I did. I loved hearing about the iterations Maddie made to get Scheduler AI to where it is today. If you want to learn more about Maddie, you can find her on LinkedIn. If you enjoyed this episode, let me know on LinkedIn or leave a review on Apple Podcasts or Spotify. Thanks for listening, and I’ll see you next week!