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Operational Debt Is Slowing Your Company | Stephanie Johnson

About this episode

In this episode of the Parallel Entrepreneur – Innovation Series, Mark Cleveland and Johnny Anderson sit down with Stephanie Johnson, a fractional CEO and COO who specializes in helping companies eliminate what she calls operational debt.

Most leaders recognize technical debt in software. Fewer realize the same concept exists inside organizations.

Misaligned teams. Unclear processes. Decisions that made sense in the moment but quietly compound over time.

Stephanie steps into companies during pivotal moments—growth, transition, or pressure—and helps leadership teams reconnect strategy with execution.

This conversation explores:
• What operational debt actually looks like inside organizations
• Why strategy often fails at the execution layer
• How leaders stabilize teams during change
• The hidden friction slowing growth
• What it takes to realign people, systems, and performance

If you’ve ever felt like your business should be moving faster than it is, this conversation will resonate.

About the Stephanie Johnson
Stephanie Johnson is a fractional and interim CEO/COO who helps organizations navigate complexity, stabilize operations, and drive sustainable growth. Known for her ability to quickly assess challenges and reconnect strategy with execution, she works with leadership teams to improve performance, strengthen alignment, and eliminate operational friction. Stephanie has led across global teams and organizations, bringing a balance of operational rigor, executive leadership, and people-centered transformation.

About the Hosts

Mark A. Cleveland
Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network
https://www.linkedin.com/in/macleveland/

Johnny Anderson
Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™
https://www.linkedin.com/in/johnnyonbrand/

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC):
https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.

Chapters
00:00:00 The idea of operational debt
00:00:44 Episode introduction + Stephanie’s leadership focus
00:01:10 What operational debt looks like inside companies
00:02:05 Why strategy often breaks at execution
00:02:58 Stepping into organizations during pivotal moments
00:03:47 Aligning leadership teams around clarity and accountability
00:04:39 Finding the friction slowing growth
00:05:26 Stabilizing teams during transformation
00:06:19 Reconnecting strategy with operational discipline
00:07:12 Leadership lessons from high-stakes environments
00:08:05 Final thoughts on eliminating operational debt

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Operational Debt Is Slowing Your Company | Stephanie Johnson

Parallel Entrepreneur with Mark Cleveland

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Parallel Entrepreneur with Mark ClevelandOperational Debt Is Slowing Your Company | Stephanie Johnson. Machine-transcribed; use the interactive transcript above to jump the player to any line.

But I have been in roles as a COO where they're like, oh, but you don't know how to be a, you're not a data analyst. I don't need to be a data analyst. It's about the people. It's about how you make them feel. And will they follow that? Will they believe in that? How do you make them feel about the safety of failing or the safety of bringing up ideas that may not be super popular? Like I feel that I've created that environment that I continue to work in that environment. And I want everybody else to do the same because that's the key. The solution doesn't lie with me, right? I lead an organization. The solution lies in every developer, every marketer, every customer success. They have ideas. You just have to find a place for them to lay them out. Welcome to the parallel entrepreneur. This is a special series on innovation supported by relational marketing and the Chase Studios recorded at the Greater Nashville Technology Council Innovation Summit. I'm joined today by guest host, Johnny Anderson.

He's the entrepreneur in residence at the Nashville Entrepreneur Center. Sit back and join us for this special edition of having authentic conversations with people that care. My name is Stephanie Johnson. I'm the CEO of Aklan Avenue. I've been a COO for a while. And so to me, I'm in the back of the leader. I'm supporting the leader from behind the scenes. And that's where I was and I was okay with that because I love being a COO because they know everything. They can see things ahead of time, that foresight, that like being able to put things together ahead of most people, right? To keep us from getting into a bad spot. But Nashville is a welcoming, it's a welcoming place. And since I've become CEO a year ago, yesterday, actually a year ago yesterday, I was appointed CEO. It's really even opened up even more for me and people have been welcoming because it's a different role. CEO is doing different things than a COO, but I would advise that most CEOs need to be COOs first. We're here to talk about technology and innovation.

And what we end up talking about is people stuff. It's always people. People stuff, right? Yes. So what's one of the biggest lessons you've learned recently? We talked about this a lot. Have to provide clarity to your team from the top down. And once you can do that, once they can understand where you're coming from and the vision and just clarity. I think one thing that I left out of here with an idea of what I wanted to do and I was so gung-ho about it, I was like, I wanted to meet in the next day. I was like, let's talk about this. I am so excited. When I got back to the office to tell my SLT though, they were looking at me like I was completely mad and crazy. You just got back from a Tony Robyn Seven. Yes. You're crazy. I'm hype. When's this going to wear off? So I mean, but it wasn't their fault. It was mine. And it's like I had to provide clarity of what I was thinking of. And they would help me with the rest. But as long as I made them feel comfortable, and you always, there's a psychological part to rolling out anything.

And especially now with AI, right? There's a lot of psychological things. You have to make people feel comfortable that we're not replacing you. Like, they have to be part of the solution. They have to be part of us getting here. And my whole entire team is part of the reason why we are prepared today. Wow, my drop. That would be the end of a normal session. This isn't normal at all. This is so exciting. You have the ability to communicate a lot of excitement. I keep listening to your voice and hearing the spirit that's in there. And I want to follow you, too. So where do people find you and follow you? Yes. LinkedIn, I'm on LinkedIn, like everybody else. That's probably the main place. I don't have any secret websites or social media accounts. But like, LinkedIn, I'm on LinkedIn. You can reach me anytime. And the thing is, it's authenticity for me. This is what you get every day. I've been to people's homes, met their husbands or wives. And I think they're all like, is she like this all the time? I'm pretty much like this all the time.

Sometimes it may not be just as scary depending on what's going on. But I'm very if you feel it, it's because I feel it. And so that's what I want. It's like, I'm telling you, this is, I'm very excited about it. And anything that I, any initiative that we come out with, I bring that when I'm, because I really, truly feel something about it. And I want people to do the same thing. If they feel strongly about something, you'll know. You'll know because you can listen to their voice and how they present the idea and all of those things. So thank you. It's true. It's a true feeling. I've listened to podcasts and I've heard a statement that kind of falls under the category of, AI is going to allow us to do more human things. It always sounded a little silly to me and I don't know that I fully understood what that meant. You made me feel that in the way that you answered that question. I think I'm getting a better inclination of what that actually means. Some of it's very much people's stuff. But I think that was the first, that was an aha moment I just had with you. Well, that's amazing. It's all about people.

I think that's where, you know, I'm a non, I'm considered a non-technical CEO, whatever that means. I kind of, I don't like the phrase non-technical CEO, but I have been in roles as a COO where they're like, oh, but you don't know how to be a, you're not a data analyst. I don't need to be a data analyst. It's about the people. It's about how you make them feel. And will they follow that? Will they believe in that? Will they, how do you make them feel about the safety of failing or the safety of bringing up ideas that may not be super popular? Like we create, I feel that I've created that environment that I continue to work in that environment and I want everybody else to do the same because that's the key. The solution doesn't lie with me, right? I lead an organization. The solution lies in every developer, every marketer, every customer success. They have ideas. You just have to find a place for them to lay them out and talk about it. Express it.

Yes, and some of those are gonna be great and some of those are gonna fail, but that's okay too. Well, there might be incremental movements towards a massive success. I hope so. Congratulations. Thank you for coming today. Thank you guys for having me. Thank you. Hey, thanks for listening to another episode of the parallel entrepreneur. And thank you to our sponsors, partners, and the special team behind the scenes that make it all possible. Be sure to like, follow, or subscribe to our podcast and get the latest updates. And to learn more about this growing community of entrepreneurs are mastermind and companion program for your parallel entrepreneur journey. Visit parallelentrepreneur.com. And of course, thank you to all the visionary guests who trust us to share their stories.

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