CEO Global Network Podcast
🎙 Hosted by John Wilson, founder of CEO Global Network and author of GREAT CEOs and How They Are Made, this podcast delivers powerful insights for CEOs and executives looking to grow as leaders and drive lasting success.
Each episode features candid conversations with high-performing business leaders, expert speakers, and industry trailblazers—all focused on sharpening your leadership edge, building resilient companies, and improving your life, your team, and your impact.
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CEO Global Network Podcast
Jamal Denny – Co-Founder & President, Kaco Systems
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What does it take to move from technical expert to effective business leader?
In this episode of the CEO Global Network Podcast, John Wilson sits down with Jamal Denny, Co-Founder and President of Kaco Systems, to explore the leadership lessons he has learned while building and growing a technology company.
Jamal shares why he believes leadership is often more practical than complicated, and how creating space to slow down, unpack problems, and find simple solutions can make teams more effective. He also explains his philosophy of “iron sharpens iron”—actively learning from peers, competitors, and other leaders to challenge your thinking and improve how you operate.
The conversation also explores how Kaco Systems is approaching AI as a way to remove mundane work and give employees more time for critical thinking and higher-value activities. Jamal discusses his own evolution from a hands-on technical leader to someone who increasingly creates value by listening, providing perspective, and giving his team room to find their own solutions.
John and Jamal also discuss failure, resilience, vulnerability, and one of Jamal’s biggest leadership lessons: the value of building and actively participating in a strong professional network.
It’s a practical conversation about becoming a better leader, learning from the people around you, and recognizing that leadership doesn’t require having all the answers.
Hi, everybody. I want to welcome you to the CEO Global Network podcast once again. It's terrific to have you with us. Our guest today is Jamal Denny. And Jamal, thank you for being with us. It's just great to have you here. Thank you for making the time to be with us today.
Jamal DennyThank you very much for having me, John.
John WilsonI just want to let everybody know, Jamal, that you're the president and co-founder of CACO Systems in Calgary. You're calling in today from Calgary. And I want to let everybody know that you came up through the technical side. Okay, you trained as a network engineer at SAITE, spent years working your way up through organizations from systems consultant, the team lead, the practice lead. And then you decided to build something of your own. And so at that time, you and your partner Kyle Benning started Keiko with a fairly simple premise. I think that was about 13 years ago, wasn't it, Jamal? It's actually just over 14 years ago. Okay. All right. Yeah, and you're no longer a startup, eh? No longer a startup. That ship is mom and gone. And I want to let people know that you had a fairly simple premise, simple but hard to do, eh? And that is to do this differently than the other technology providers out there. You built CACO around the idea that a great IT partner shouldn't just solve problems, but they should understand the business, challenge thinking, help their clients make better decisions at the end of the day. And here we are 14 years later, and the firm handles cybersecurity, very successful firm, network infrastructure and managed IT for organizations across Alberta. And so congratulations to you and your partner. I just want to take a second at the risk of going too long with this intro. I want to let people know a little bit about your personal life, Jamal. I want them to know that outside the office, sport is a big part of who you are. You're a player, not a spectator. Okay. Spent four years as the president of the Calgary Rams rugby club. You ran the club, you represented across the community. You also play basketball. And I read somewhere, Jamal, that you recently took up boxing and that you you would you want to tell everybody on the who's listening that it's much harder than it looks. Quite frankly, to me, it looks quite hard.
Jamal DennyYeah, and certainly it is harder. And and the interesting thing is that, you know, I'm I'm a somewhat of a bigger guy, taller, and maybe a bit heavier than I need to be. And people will look at me and they would say, Oh, you know, you're a shoe-in for boxing. You're so big, and so on and so forth. But they forget that the people I'm fighting are also big and lot. It's nothing's granted, but for me, it was a real transition because I you mentioned I a lot of rugby, a lot of basketball. So these are like true traditional team sports. Go to boxing where you still have a team of people that you spar with, your coach, and so on and so forth. But there is far more drive in that sport that you need to have as an individual than you would have when you're playing basketball, when you can rely on the point guard that's going to score the 30 points to go in and do some rebounding. So it was a great sort of mental test. I haven't necessarily hung up my gloves, so to speak, but I've kind of put that on the back burner to do some other things right now.
John WilsonGood for you for doing it. I also want to just mention that you've given a good number of years to Big Brothers, Big Sisters as a mentor. And when you're not on a pitch or in a gym, you're off exploring somewhere new with your wife. So I wanted to mention that. I also want to let people know that you're a member of SEO Global Network and Mike Ross's group in Calgary. And it's great to have you part of that, Jamal. I got six questions for you that I just want to ask you the first one. And then hopefully we'll get through them all in the next few minutes, okay, just depending. But the first question I have for you is I've heard you say that leadership is practical. What's one simple habit that's had a big impact on your team?
Jamal DennyYeah, I would say just kind of keeping it simple. Solution is usually a simple thing. It doesn't have to be anything too over-engineered. And so really it's just a matter of giving the team and myself the time to sit down and sort of unpack what it is that we're trying to solve. And more often than not, in those conversations, we're figuring out what that easy path is. So that's really the habit that we try to lean into the most within the group.
John WilsonYeah, that's an important one. You've written that iron sharpens iron. How do great CEOs create an environment where people challenge each other, sort of iron sharpening iron, in the right way?
Jamal DennyYeah, so I kind of picked up the iron sharpens irons thing from when I started boxing.
John WilsonSports, yeah.
Jamal DennyAnd because how you get better at boxing is that you spar with other people that are different skill sets, maybe faster, maybe hit harder, all that kind of thing. And so for me, I think it's important for me as a leader to be going out there and meeting with various people, various organizations, some in competition to what we do, to understand how they do things. And so I'm very much a uh sort of a lead from the front type of individual. And so I do that, and then I come back and the team we meet every every other Friday. I'll talk about what I've done out with the people that I've met with and kind of have an open conversation about here's how Company X is doing things. And I really think they're doing a great job. And so let's talk about how that would work well in our organization. And it's amazing to see that over time that the team is starting to pick up on this concept of iron sharpens iron, and they're out there talking to others, talking to the competition, hearing how other people are doing it, and it's starting to work their way into the solutions that they're providing to their customers. So it's something that I feel like we've done sort of here and there throughout the time that we've been spending here at Keiko, but to give it a name really kind of creates a bit of a rallying cry around it. And we found that it's increased considerably now that we've kind of had this term that we can all relate back to and celebrate.
John WilsonYeah. It's a great rallying cry. So, as a technology leader, how do you keep AI focused on enhancing people instead of replacing people? How do you do that, Jamal?
Jamal DennyYeah, I think we try to do a good job. Like we have some initiatives. The main initiative I would say is that we've sat down with the team and given them an ability to have a process to effectively think of the more mundane tasks that they do day in or week out or whatever, and figure out how we could automate it or simplify it or revamp it altogether so that they have more time to do some of the things that they're more uh engaged on, so that they have more time to critically think on a solution that they're gonna do or to spend some time to investigate a technology that they haven't otherwise had the time to investigate. And so it's providing some guardrails for how we support the team to identify a particular task. It's a pretty well-developed process. Identify that task and figure out the steps that one would need to follow to make that task something that is handled by artificial intelligence.
John WilsonThat's terrific. That's terrific. Yeah, help people work on their highest best use rather than on the mundane.
Jamal DennyYeah, start working on the $100 an hour stuff instead of the $5 an hour stuff.
John Wilson100%. Yeah, for sure. Now you built your career by staying pretty hands-on. How do you know when to step in and when to let your team figure things out for themselves? How do you handle that?
Jamal DennyIt's been a bit of a journey, to be honest, because more or less I've had to step away from the technical side so I could focus on getting gearing up on the strategy and running the company and so on and so forth. So being a fairly highly talented, I'll pat my own back here, I'll pop my own tires here, technician. It took me a while to figure out where I could provide value outside of delivering solutions. That's a journey, and that's part of why CEO Global has been so great to me. But now I can appreciate the team, very strong team, very capable team, and where I can fit in, where I can provide value. Sometimes it's just listening, sometimes it's providing a bit of guardrails on where the solution can or should be going. But more often than not, it is just listening and just being a bit of a sounding board. And it's amazing that, you know, I can kind of sit here and be welcoming and listening and maybe not say a lot of words, but they're coming out with their own solutions. And I look like I know all the answers to all the world's problems. So that's really growing into this role that I've, to be honest, had for a long time has really taught me to where I can still provide value, maybe not so much on the keyboard and the technical side, but just again, helping the team get through, see a different light of see a different light on things.
John WilsonYeah, different perspective. Well, yep. Thank you for that. Building a successful company certainly has speed bumps and challenges along the way, Jamal. How have some of these challenges shaped the way you lead today?
Jamal DennyThat's a great question. I think the challenges that I've faced, initially I'm hypercritical of myself, I would say. And so some of the journey with these challenges, I would say, have been caused me to rethink sort of how I'm doing things, why I'm doing things, so on and so forth. And kind of feeling that I'm the guy on the island on his own trying to figure his way out. But it's through conversations with like the whole Iron Sharpens Iron Sink, talking with other people, hearing their stories, finding out that I'm not the only one, and kind of digging into the fact that yes, I'm not necessarily knocking it out of the park every single time. But if I do strike out, I'm knowing why I struck out so that the next time I'm at that, it's a home. I don't play baseball, but it's a good analogy though. It's really that. It's just sort of taking comfort in the fact that I'm imperfectly perfect. And so I just need to, yeah, lean in on that or lean in on the fact that my road to where I've gotten and where I'll continue to go has some bumps. I would say the majority of the people that have similar operations, whether it's an IT or otherwise, would have similar things to say. And that's there's some comfort in that. And there's also comfort in the ability to not languish in that, move through the failures that you have and ultimately celebrate the successes when they come up.
John WilsonNo, 100%. No. As a fellow entrepreneur, I could totally relate to that 100%. Jamal, I got one last question for you, and then we're going to wrap up. When you look back at your journey, you went from engineer to entrepreneur, CEO of the organization. What leadership lesson took you the longest to learn? Is there one that kind of you pops off the page? I wish I could have learned this one quicker.
Jamal DennyI think like the network, your social network is probably the strongest thing that you have available. And it took me a long time. Some of that is built into being a tech guy. I am sort of somewhat introverted in in many ways. And so I didn't appreciate it for what it was. But I've recently just started to be more proactive while in reaching out. And it's amazing how willing people are to have a coffee, to give you some insight, to in some cases, even throw you some business. All it takes is just reaching out. And so for the most part, I would say that I try to do good by people as much as I can. And so I'm fortunate in the sense that perception of myself by my peers is quite positive. So I've had this network and this, these connections available to me for a long time. And I didn't make good use of them. I didn't grow them. I didn't provide, I wasn't an active participant in the community to the point where I am now. So certainly, if I would have known that as I was an engineer, I think that would have made the transition into being an entrepreneur, the ability to be like open and vulnerable with people that I knew would be able to understand my perspective, that much more easier.
John WilsonJamal, that's a fantastic response to that question and such a terrific lesson for all of us. So I just want to thank you so much for being with us today. I know you're a busy guy. You got a lot going on, but it really means a lot to us to have you here and have you share some of the lessons that you've learned along the way with us because they'll help us along the way too. So thank you so much, Jamal.
Jamal DennyJohn, I appreciate it and always here to support. Love the the last couple of years that I've had as CEO Global and looking forward to a few more.
John WilsonNo, that's wonderful. Yeah, it's great to have you part of it. Thank you. Thank you.
