Ready.Set.Midmarket! Podcast: Tackling Tech Debt With Ken Knapton

In this episode: Dr. Ken Knapton discusses how organizations can manage technical debt.

Technical debt costs organizations nearly $3 million a year. Tech debt accumulates when companies take shortcuts when writing code, by not updating legacy hardware, and for other reasons. Adam Dennison, vice president, midsize enterprise services at The Channel Company, and Samara Lynn, senior editor of MES Computing, speak with Ken Knapton, a seasoned IT leader and the author of “Unveiling Tech Debt: A Business Leaders Guide to Measuring and Managing Enterprise Tech Debt Leverage,” about how midmarket IT leaders can recognize and address tech debt.

Previous Ready.Set.Midmarket! Episodes:

The Midmarket’s Tech Road Ahead In 2025

Leading The Girl Scouts’ Technology

Transcript:

Adam Dennison: Welcome to Ready.Set.Midmarket!, MES Computing’s podcast for all things midmarket IT. I’m your host, Adam Denison. And joining me is senior editor of MES Computing, Samara Lynn. Welcome, Samara. So our topic today is around tech debt. And we have an expert in that field joining us. We have Ken Knapton. He’s the CIO of Win Brands. Ken, thank you so much for joining us this afternoon.

Ken Knapton: Thanks so much for having me.

Adam Dennison: You bet. Ken, before we get started and into the topic of tech debt, can you just give us a little bit about yourself, your background, introduce us to win brands, what are some of the brands that you have, what’s your portfolio look like?

Ken Knapton: So as far as my background, I’ve been in the IT industry for, oh, a long time now, 30-something years, started out as a software developer. So I’m kind of that, that hands-on coding kind of guy, thought that’s what I was going to do for my entire career. ‘Cause I just absolutely love, you know, the logic, the analytics, all that kind of stuff. But, you know, I spent my career really focused on a couple of key topics.

Data has been a key element for me, security of that data. And then, you know, I’ve really kind of, as I’ve woven through my career, worked my way up through the architecture ranks of CTO, CIO. So I’ve been in multiple seats, but really I’ve focused most of my career on kind of that enterprise level of software. So as I moved from the CTO seat into the CIO seat, started kind of wrapping my mind around more of the operational aspects of IT. That’s really when I started to kind of open my mind around some of these topics that we’re gonna be talking about today as we get into it. So I don’t wanna go too far down that path yet, because that’s what we’re gonna talk about, but that’s kind of the progression of my career, right? From kind of the software developer up through to the CIO seat where I’ve been for the last 20 years.

So I’ve worked in a lot of different industries, mostly highly regulated industries for some reason. I’ve been in healthcare. I’ve been in finance. I’ve been worked in nonprofit for a bit today. I’m here with, with WIN Brands and we have really two primary brands that fall under that organization. There’s Costa Vida, Fresh Mexican Grill, which is a casual dining entity, Mexican food, really multiple states, about a hundred locations right now and growing. that’s the Costa Vida side of the business. And then we also have a brand called Fat Cats, which also [is in] multiple states. But these are, are large, like 60,000 square foot buildings that, that are really a family entertainment center. So cinema, bowling, arcade, you know, all under one roof. We’ve got mini-golf. And of course, you know, we have a grill with, with outstanding food there as well.

So, you know, this is my first foray into kind of the casual dining and entertainment space, but really doing the same thing that I’ve been doing forever, which is, you know, watching over IT systems and data, you how the data flows and making sure security is where it needs to be. So that’s a little bit about me.

Adam Dennison: How many locations you serve? What states?

Ken Knapton: So, we’re based in Utah. And so, our primary kind of footprint for both of them is Utah, but we have locations, Fat Cats, Arizona, Idaho. So, we’ve got a couple of states that border us. Costa Vida is a little bit larger. So, we have locations in California, Arizona, and Idaho as well. We have some out in Kansas. So, we’re all over with Costa Vida. And like I said, continuing. to grow where we just opened a new building what two weeks ago and several more on the docket for this year.

Adam Dennison: So, I’m in Boston, Samara’s in New York City. You got to start heading our way so we can experience these.

Ken Knapton: We’re on our way. We’re coming. Got it. Sunday we’ll be there. Yeah.

Adam Dennison: I love Mexican food and my first job ever, was a dishwasher at Chi Chi’s Mexican restaurant in Erie, Pennsylvania. You learn very quickly that you want to educate yourself and aspire for more whenever the lunch crowd starts piling up on you there. It can be very challenging.

Ken Knapton: I was a waiter for a period as well, not Mexican food, but yeah, know it really is a lot of fun. This has been an interesting transition for me. And I’ve been a fan of Costa Vida and Fat Cats living here in Utah, experiencing both of them. I’ve been a fan of both for a while, but yeah, the food at Costa Vida is just phenomenal. So, friend of you listening, if you’re near a Costa Vida, go try it out. Let me know.

Adam Dennison: They wouldn’t let me in front of house due to my job descriptions. So, thank you for the background. That’s very, very helpful. So, on the topic of tech debt, I’m not a technologist. I just happen to be in the field. Can you share a little bit around your vision of tech debt, define it maybe in terms of a lay person like myself that’s on the general business side of the house? What does that mean? Why is it important? Why should another businessperson outside of the tech team, the IT team, why should they care about it and kind of give us that overview?

Ken Knapton: Yeah, I’d love to. So, and this kind of ties into the intro when I was telling you about my background. As I said, I started out as a software developer and then kind of moved into kind of other operational space. And this concept of tech debt has really taken a similar path. So super kind of brief history here of the term. The term tech debt was coined in the early 2000s. And it was around the time of the signing of the Agile Manifesto. For those of you who may be familiar with the Agile world, Ward Cunningham really coined the term and at the time he was focused specifically on software development.

So those people who were writing code, hands on keyboard, building those systems that would go out the door to customers. And his definition of tech debt was really around those decisions that were being made by developers in order to hit a release date, in order to get something out the door. So maybe they might cut corners a little bit or they might do something for the short term without really planning for the long term, or maybe they knew that this wasn’t gonna scale, but in order to get it out the door quickly, they needed to do it this way. And so that would inhibit the growth, it would inhibit that progression of that particular software. Now at the time, the thought was, well, we always have time to come back and do another release, right? Release something else and update it, and then we can fix that. But that was kind of the initial definition of tech debt.

So, my definition, and really, I don’t want to say that I’m taking credit for expanding the definition here, because I think it is something that’s being talked about more generally than that. But the definition of tech debt today really expands beyond that and really does move into that business-centric realm. So, the way that I define tech debt is that it’s any aspect of our technological stack, any aspect of that tech stack within an organization that inhibits the advancement of company goals, right? And that could either be due to design that didn’t contemplate either the current or future desired state, or which may stem from the lack of maintenance or the lack of upkeep of that tech stack. So, from a business perspective, what this means is, let me just put it in the context of a company I used to work for. So, I was working for a company, they were talking about tech debt all the time. This is holding us back, our tech team. And at the time, they were blaming the IT team itself, right? these guys, we’ve got to get smarter people. They’re not moving fast enough. They’re not able to, you know, get stuff done that we need. Well, as we dove into it, started to realize that it wasn’t necessarily the individuals, the tech team that was struggling. It was the fact that some business decisions had been made that, we’re not going to invest in upgrading that server because we want to spend that money on marketing or somewhere else in the business. And so, these decisions over time would build up in the tech stack itself to where we had servers that were four or five major versions behind on the operating system. And so now when someone in some other part of the business says, hey, we have this new system, we’ll go to a conference and I learned about some new tool or something that I want and I want to come back and tell my IT team to go install that, they can’t do it. Not because the IT team isn’t capable, it’s because we’re too far behind on operating systems. We haven’t kept up.

And so, we can’t install that here. And we can’t just upgrade because we have all these critical systems running that are going to have to be modified and changed in order to upgrade this operating system. So that is one aspect of tech debt. It’s not maintaining our systems. It’s also decisions that we make that maybe are a good decision at the time. Maybe it’s a good business decision to say, we’re not going to upgrade this server because we have to do this in order to grow our business.

But if we don’t come back and address that, then that grows, that becomes a larger, the way that I term it is we have increased tech debt leverage. So, we’ve highly leveraged our business on the technology side, which is now inhibiting our ability to do the things we need to for a business standpoint. So that’s kind of my definition of tech debt.

Adam Dennison: So, what’s the recommendation on, I can see it, right? You’re in a board room or an executive committee team, maybe not to the board yet. And the CIO, the CTO, they see this, they see the problem, they see down the road, they see where the company wants to go. How do you have those discussions with non-technical people to let them know that I actually need to do this? We need this budget and this money now because you’re not going to be able to get to where you want to get to. And the discussion we’re having 18 months from now is going to be a lot harder than it is today.

Ken Knapton: Yeah, that’s exactly right. And that’s exactly the conversation, right? And historically, because I’ve been in that chair trying to explain, hey, this is holding us back. It’s going to hold us back. We can’t get where we need to. And historically, I think many IT leaders, CIOs, CTOs, whomever, right? I think they’ve attempted to educate their executive team and their board about computer science, right? They tried to educate them about infrastructure and when you need to learn about all this so that you can understand what I’m talking about. that’s, that’s never been successful, right? Because boards, you know, they, they’re focused on running the business and you know, I don’t want to say that they don’t, that they can’t understand this stuff. Just not in their realm, right? It’s not, it’s not in their area of focus.

So, what I recommend is the old adage of what, what isn’t measured, isn’t managed, right? If you don’t measure it, you can’t improve it. So, we have to quantify that tech debt in terms that they understand. And that’s why I use the term tech debt leverage. So now if we can talk to a CFO or a CEO in terms of how leveraged are we within our tech stack, they understand that because they’re always talking about financial debt leverage, right? They understand the concept of debt leverage and financial debt leverage and tech debt leverage are actually very similar. They both can be positive or negative. They both can help grow a business and they both can hold a business back. And so, once you start talking in those terms, then you can start to make those connections without having to educate them about our entire tech stack, right? So how do do that? Well, you have to evaluate your tech stack. You have to measure the leverage of tech debt across that tech stack. And then you have to put that into numbers and bring that in front of them. And that’s, and that’s something that I’ve been working on for a couple of years is figuring out those algorithms to kind of put those numbers together so that you can put them in front of a CFO or a CEO and it’s something they understand.

Adam Dennison: And is it, are they accepting of it? They get it?

Ken Knapton: So, yeah, so I’ve been talking about this for a couple of years now, and I have a book on the subject. I’ve written a couple of papers on the subject for IDC as well. And every time I present on this; I present to CIOs and CTOs. I also present to businesspeople. And in both cases, the light turns on.

When I start talking in these terms and I show them here is how you can measure, here’s how you can quantify. And then as you quantify, here’s the way that you can present this in a meeting. Here’s the dashboard, right, that you can show that allows you to talk about this in business terms that people who are not technical will understand. And in both groups, the light really turns on and they’re like, yeah, this makes a lot of sense.

Samara Lynn: When I was in IT, we were always designated as Capex, right? Capital expenditure. But the thing is, digital transformation and investment in IT helps for long-term success for company. So, isn’t tech debt kind of just inherent with IT? I mean, isn’t it expected? Like, I’m always surprised when CFOs and other management leaders are like, well, why is there debt? Because this is an investment.

Ken Knapton: Yeah, yeah, no, you’re spot on. And that’s one of the things that I bring up frequently is this idea of people always say, how do we eliminate our tech debt? And my answer is you don’t. You will never eliminate your tech debt, right? And even with SaaS solutions, there is still tech debt in SaaS solutions because as soon as you implement something, let’s say, for example, that you’re implementing something like a cloud solution, right? Like Salesforce or whatever, right? That’s out there.

You’re going configure that to meet your needs. And it’s an operational thing, right? Even though it’s not a capital expenditure, right? It’s an operational thing that’s being utilized. You still configured it and developed it for your needs. Well, your workflows will change over time. You’re going to need new capabilities, and those cloud solutions will come out with new features and new capabilities. I was working for a company once where we had a solution in place.

And it had been so highly customized. It was a SaaS solution, so highly customized. It took us 18 months just to accept their upgrade because of all the changes we had made. That’s tech debt. Customized it and changed it, again, maybe for good reason because we had workflows that required that, but we changed it so much that when a new feature came out that we wanted, we couldn’t take advantage of it because we couldn’t accept that upgrade until we took all of our custom code and got all of it upgraded with it. So even with SaaS solutions, tech debt: Was that one of those customized systems that Dave or Nancy own and work on and they had better not go anywhere or we don’t know how to continue to run this?

There was definitely an element of that to it. Yeah. That over time, you know, that knowledge resides in one person’s head or a couple of people’s head, right? That tribal knowledge is very risky.

Adam Dennison: Well, I think it’s interesting you mentioned cloud. I was just kind of thinking of the I’ve been in high tech now for a number of years. And you think it’s sort of these inflection points with cloud, with mobile, with security now, obviously AI. When should a CIO, CTO start to see these inflection points coming in and think now I need to make the case because I know that the CEO of the board, whoever it is on the other other side of the business is going to start coming to us and saying

Now we’re behind. You hear that a lot right now with AI. We’re behind, we’re behind, we’re behind. And then you also hear folks say, well, we’re not ready for it. So, if we’re going to institute it, it’s not going to do much for us because of XYZ. So, what would the advice be in terms of getting a sense of where those down the road, where this is going to be a problem and how to have that discussion ahead of time? And to at least cover your backside, it said we had this discussion, and we documented it.

Ken Knapton: Yeah, you know, that’s a great question. And so, a couple of thoughts come to mind. One, I view my role in the CIO seat. You know, my job is to ensure that my team are operating the business on a daily basis, right? They’re doing the daily things there. They’re supporting operations, so they’re very much, you know, today focused a lot of the team, right? My job is to be looking six to 12 months down the road to say.

This is where we need to be in order to meet our strategic goals. So I have to understand the strategy of the overall organization, where we’re headed. And I have to be looking down the road so that I can be funneling that into my team to be establishing those capabilities when we need them. Right. Because again, you know, it’s kind of that, that’ll, you know, Wayne, Wayne Gretzky quote, right. That you’re going to go to where the puck is going to be. Right. That that’s kind of the job of the CIO.

But from a tech debt perspective, you’re right. It’s one of these things that can sneak up on you if you’re not measuring it and managing it and watching it. And I think you bring up AI, that’s a perfect example because AI really kind of came out of nowhere. I mean, it’s been around since the 1950s, but chat GPT came on the scene and it really kind of all of sudden exploded, right? And so, a lot of companies are scrambling right now saying, hey, we need to implement AI and we’re going to do so. The best way to do that is to get your information into the model so that you can operate on your data. Well, most companies don’t have their data ready for AI. So the data itself is now tech debt because the AI model is there. You can get an AI model and bring it into your environment. But if you can’t get your data clean and put it into the AI system, you’re not going to be able to evaluate your own data, your own systems. And so the data itself now has become tech debt because that’s what’s holding you back from being able to leverage those capabilities.

Adam Dennison: I had an MES dinner with about eight IT leaders and a vendor, and the president of that vendor said that ChatGPT, he likened it to a 12-year-old just memorized the internet. Be careful what you’re going to get back.

Ken Knapton: Yeah, it’s true. you know that this there’s another article that I’ve written on that very concept, although the potential biases that are in the data and the prompts, the way that you prompt it, it really that that training set really matters. And again, when you take your own data and put it in, you know, it’s garbage in garbage out, right? If you haven’t maintained and called and, you know, cleaned your data, you’re not going to get great answers.

Adam Dennison: So, we’re getting close to the end. Samara, do you have any final questions? for Ken?

Samara Lynn: Just one quick question, Ken. What is the best way for a midmarket IT leader to pinpoint tech debt in their organization? Any tools, any sort of...?

Ken Knapton: Yeah. Well, I mean, I don’t want to, you know, self-promote here, but I would say the best advice I can give you is go take a look at my book on tech debt. I outline in there all the specific ways to quantify it, how we go about doing that. So that’s a great tool. And actually, the reason why I did that is because I couldn’t find any other tools. All of the tools that I found were all around that concept of software development tech debt. And so, so this is really that that’s really why I went down that path.

Adam Dennison: So, name of it and how can people get it?

Ken Knapton: It’s called “Unveiling Tech Debt.” It’s available on Amazon. yeah, then feel free to reach out to me as well. I’m happy to answer any questions.

Adam Dennison: My final parting question is just get to know you a little bit on a personal level. you have three days off coming up, which you probably don’t. What are you going to do?

Ken Knapton: You know, looking out behind me here with the clouds, I’m waiting for a nice day with three days off. I would probably get on my bike and go ride up the mountains there behind me. I just, really enjoy riding around here in Utah, getting out in the beautiful weather.

Adam Dennison: I have a big night tonight. I’m the coach of my seventh-grade daughter’s middle school team for basketball and we’ve got playoff game number one tonight. So that’s four months in the making. So hopefully we don’t disappoint tonight.

Ken Knapton: Yeah, well, congratulations and good luck.

Adam Dennison: Thank you very much. Again, thank you so much for taking the time out to join Samara and I on our third episode of Ready.Set.Midmarket. To those of you, the viewers, thank you for spending the time with us and have a wonderful rest of your day.

Ken Knapton: Thanks so much.