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Rob Zelinka
Vice President & Chief Information Officer, Jack Henry & Associates, Inc

CIO Rob Zelinka on AI, Resilient Leadership & Building a Legacy That Outlasts You

🎥 Jul 10, 2025 📺 The Software Leaders Uncensored Podcast ⏱ 23m 👁 34 views
In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Rob Zelinka, a seasoned tech leader with ...
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About Rob Zelinka

Rob Zelinka, Vice President and Chief Information Officer at Jack Henry & Associates, has been discussing the rapid pace of technological change and the importance of embracing artificial intelligence. In multiple interviews in 2024 and 2025, Zelinka stated that AI is "moving faster than any technology that I have seen in my 30 plus year career" and advised others to "embrace it, use it, but trust and verify it." He has also spoken about the need for governance around AI, noting that companies must "come up with governance for how they're going to manage the use of AI technology." Zelinka has emphasized that while technology is a differentiator, it is not a replacement for people, and that the human element remains critical, particularly in client-facing roles. Zelinka has also discussed his leadership philosophy, which he described as "servant leadership," and his focus on building high-performance teams. He has said that his goal is "to be a good human and make a positive difference in as many people's lives as I can." In a 2025 interview, he stated that "the more problems and obstacles you move out of your way, the more money you make," and that failure is a natural part of growth. He has also commented on the challenges facing CIOs, noting that the average lifespan in the role is around 18 months, calling it "almost an impossible job."

Source: AI-verified profile updated from Rob Zelinka's recent appearances. Browse all interviews →

Transcript (41 segments)
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Steve Taplan0:00
Welcome to Software Leaders Uncensored with Steve Taplan. Welcome to Software Leaders Uncensored. I'm your host, Steve Taplan, 25-year serial tech entrepreneur. My new book, Fail Hard, Win Big, comes out in July 2025. I'm excited about it. This is my story of having 30 ventures with 20 failures and 10 wins. Used to be embarrassed saying that, but I'd take a step back and say, 'Hey, if I was in baseball, that'd be a .333 lifetime batting average. That would get me in the Hall of Fame.' Common element of all my companies is I've always built custom software as the operating system for the company for internal processes to make unique client experiences and increase enterprise value. Now, through my company, Senatifi Technology, we help others with custom enterprise software development. Today my guest is Rob Zelanka out of Houston, Texas. Rob has decades of experience in digital transformation, service management, cyber security, been tech leader, CIO. Rob, welcome to the show.
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Rob Zelinka1:06
Thank you, Steve. So happy to join you tonight.
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Steve Taplan1:09
Rob, please give our listeners a couple minute overview of the journey of your career.
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Rob Zelinka1:14
Yeah, absolutely. So, you know, I was at a young age, newly married, trying to sort out what I was going to be when I grew up.
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Steve Taplan1:22
Full head of hair then?
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Rob Zelinka1:23
Yeah, I sure did have a full head of hair. Thanks, by the way. Thank you for noticing.
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Steve Taplan1:29
I'm not far behind you.
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Rob Zelinka1:30
It's okay. Um, and ultimately I was doing noble work. I was working in a restaurant, tending bar, serving food. And it was at that point that I realized while I was making really good money, it wasn't a sustainable way of making a living. And I was enamored with technology at the time. This was at the juncture where everything was starting to evolve from a technology perspective. The internet had made its way onto our scene. Computers were making their way onto the scene. And so these restaurants and bars that had these old-fashioned cash registers with the button and the big cash drawer that would come out and hit you in the stomach, that was being replaced by a computer. And no one knew how to set these computers up, connect them, much less use them. And I was just at the intersection of human behavior and technology. And that was the first time I was at that intersection. And I said to myself, I believe I can make a living doing this. I have a passion for teaching people, helping to enable people. I have a passion for technology and that technology is the strongest enabler. And so my journey started there and it kept going and going. There were various inflection points throughout my career. The first being the events of 9/11. What a horrible day in our lives. But boy, it did teach us quite a bit. I was there. I navigated that. And then the next inflection point after that was the financial crisis. And I learned the art and skill of cost containment, cost avoidance, cost optimization. And there's been various inflection points since then. Most recently of course leading and navigating companies through the use of responsible use I should say of AI. It's amazing how major events and dealing with those challenges shape us as leaders on how we deal with those things, how we make it through it, and our ability to solve the challenge, the unexpected challenges that those bring, and get our organizations through the other side.
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Steve Taplan3:23
No doubt. Absolutely. Rob, before the show, you were telling me a good story about how you were at a presentation with a representative from one of the Toyota subsidiaries. I'll let you tell the story, but talking about how every company is a tech company right now in some shape or form. Tell our listeners that story if you would.
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Rob Zelinka3:45
Yeah. Steve, you know, it was really an impactful moment in my career. I love to learn from others. I learned at a very early stage in my career that I need to find a room where I'm the dumbest guy in the room and surround myself with knowledge, skill, and experience and just sit there and learn from people. To that end, I went and listened to a gentleman who was the CIO of Toyota Motor Sales at the time. And he was discussing, first off, he pulled the audience of technology leaders and asked a simple question, what kind of company do you think Toyota Motor Sales is? And of course, everybody in the room naturally gravitated towards, 'Hey, we're an automobile company.' Nope, we're not. We're a technology company. And the room was silent for the moment. And he went on and he talked about how many computer systems are in a vehicle that's manufactured and what all these systems do and how they're interconnected and how they drive human behaviors. And the thing that was really provoking for me is how they were talking about moving towards a subscription model. So, think of it this way. Steve, you live in a nice warm climate. I do too where we don't have to deal with the adverse harsh winters anymore. But there's a couple days a year in the winter where we would love to have a heated steering wheel and maybe some heated seats. And what if we could subscribe to that for a couple of days, weeks, a month, and all of a sudden the technology just gets turned on. That was really impactful for me because I was thinking differently about technology. And so I carried that forward in my career. And when I joined Jack Henry many years ago, they are a very conservative company that supports financial services clients, banks, credit unions. When you think of the traditional banking experience, it is traditionally going into a branch and interacting on a human-to-human level. Think of the days where you would get paid with a piece of paper, a check. You would sign the back and you would walk in and hand it to a human that would deposit it into your account. And you walked out and you then began paying your bills through check writing. That wasn't that long ago, actually. Now, fast forward to today. Everyone, no matter how old they are, whether they're a young kid in high school, whether they're a college student, a newly married human, a grandparent, they're paying their bills online. They're using their mobile phone to conduct business. Those systems that we depend on, we rely on to drive an experience were never built for today's modern world. They were built for yesterday's world. They weren't even built for the internet, Steve. So, you know, to be able to help a company navigate through times of change and to be there to help people understand why that change is going to be meaningful and impactful in a good way and not a bad way was really rewarding.
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Steve Taplan6:26
So, certainly throughout the past 30 plus years, I think all of us, all us old guys can say, 'Wow, I can't believe how much things changed during this period or this period or this period.' But I think undisputedly the last two years with the emergence of generative AI and all it's brought to the table has fast forwarded things at a level that I don't think will slow down in the future. What are your thoughts? Am I crazy? Were other parts of the last 30 years more impactful than what we've seen the past two years?
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Rob Zelinka7:00
Yeah, that's a really thought-provoking question. So, I have two thoughts there. First, in response to are you crazy? I think we're all a little crazy to some degree, but you have to be because you have to think about the art of the impossible and usually people say what is the art of the possible? What I'm saying is you have to expect the unexpected now. AI a couple of years old really but it is moving faster than any technology that I have seen in my 30 plus year career. I was there.
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Steve Taplan7:31
So I'm not crazy. You're saying?
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Rob Zelinka7:33
Nope. Absolutely not crazy. It is moving.
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Steve Taplan7:35
You get to know me a little more, still think I'm crazy, but not at least for that opinion.
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Rob Zelinka7:39
And Steve, here's the most important thing to remember. We have to embrace this as something that's going to help drive a positive outcome. We also have to keep in mind there are people out there that have malicious intentions and they will use this technology as a way to create fraudulent behaviors and activities. And so we always have to keep our guard up. And there's this balance. When I think of AI and I specifically think of the financial services industry, for me, the most important element of helping people get comfortable with this new technology is to come at it with a framework, a mindset of using it in a responsible, consistent manner. And that takes a lot of thought and it takes a lot of planning. Sure, it would be lovely to just rush right out and start using it, but you have to start thinking about how it's used, how it's consumed, how it's managed, and you have to have a framework and some governance around it.
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Steve Taplan8:34
So, Rob, you're starting a new chapter in your career. You've started a strategic advisory called leadership life and legacy. Tell us about it.
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Rob Zelinka8:43
Yeah. So, one of the things that gives me great joy is the ability to help someone and to teach someone and to learn from someone. And so, what I've come to understand over the multiple years of my career is that my career is a journey and along that journey were stops along the way. And I was blessed with being mentored by some incredibly knowledgeable and talented people. I was blessed with the opportunity to live abroad and experience different cultures and different approaches to solving problems and leading your life. So what leadership life and legacy is all about is sharing leadership concepts with people no matter what juncture and stage in their career they are. They could be learning as a new leader. They can be an experienced leader, an executive leader or points in between and then applying those leadership principles to your life. I mean, at the end of the day, Steve, we're all human beings just trying to make the world a better place. And we all have the same stresses and challenges, maybe at different times. And so, through the course of my life, I've experienced certain things that might be useful or helpful to you. And at the end of the day, you get further down the runway in your life and your career, you're building your legacy. And what you don't realize immediately but you realize down the road is your legacy was being built starting when you started your career, actually when you started your life. That's when people started to get to know you and understand what you stand for, what you believe in. So taking those three things together and bonding them together, I'm just there to share my journey and tell a story or two along the way. And my goal is to impact as many people in a positive way as possible. Along with the consulting and advisory services are fantastic.
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Steve Taplan10:28
Fantastic. Let's talk tech challenges. Rob, what as a tech leader in the world today, what do you think are the biggest challenges that everybody is facing right now?
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Rob Zelinka10:39
I think it's just you're drinking from a fire hose. And of course, you know, I was taught growing up in the Midwest to eat every morsel that's put on my plate. The reality is the plate is just too large and I can only consume so much. So I think what we have to do is we have to manage some perspective. Give ourselves a little grace. Set ourselves up in meaningful junctures along the way. I learned something years ago. The way to eat an elephant is one bite at a time. So start one bite at a time. Have a plan for how you want to embrace a new technology, in this case AI. Learn about it. Be curious. You know your book is intriguing to me. Failure is a natural part of life. It's a natural part of learning and growth. Without failure, you don't grow. Michael Jordan, you and I grew up in the Midwest. We watched probably what is largely going to be thought to be one of the best basketball players.
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Steve Taplan11:33
Ruin basketball for me growing up in Chicago, having been to over 30 Jordan and Pippen games. Nothing has lived up to that.
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Rob Zelinka11:42
And I feel the same way. But think of it this way. Michael Jordan talked about this. He's missed more shots than he's taken in his career.
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Steve Taplan11:50
Yes. And the only way he started being more successful at making shots was to take more shots. And so that's the hardest thing right now is you have to be comfortable with failure. And you have to be willing to be vulnerable. And you might be vulnerable on a big stage in front of your peers, in front of your customers, in front of your boards of directors. You have to be comfortable with failure. And if you're not, it will hold you back. My book is based on that concept as an entrepreneur and I used to be embarrassed by the failures that I've had and it was about embracing it as it's really a superpower. And guess what, we're allowed, we're humans like you said, we're allowed to get upset, we can be mad, but you got to shake it off. My rule is you get one day to be upset, complain, whatever, you shake it off, you come fresh and you attack new problems. That's a big concept of my book is not being ashamed of failures but making sure you're turning your failures into superpowers. Because I don't know about you, Rob, but I wish I could say I learned as much from my successes as I have my failures, but that's just not the case.
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Rob Zelinka12:56
No. You know, Steve, the true mark of a person is often noted during the real challenging times, not when things are swimmingly good. You see the true mark of a human when they are put to the task. That's the true person that you're working with.
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Steve Taplan13:11
I run a software development company. I always tell my clients, it's not about when things are perfect because that's not how custom software development is. When things go wrong and we work together to solve those, that's our opportunity to create customers for life. And they're like, 'Wait, what do you mean stuff's going to go wrong?' These three other companies told me everything would be perfect. I'm like, 'That is not the world of custom software development.' So I definitely agree with you there. So Rob, if you have a good friend, a family member, a young aggressive career professional who wants to be a CIO or CTO, what would you tell them?
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Rob Zelinka13:51
So I would tell them be curious. Ask questions. Ask the hard questions. Don't be afraid to fail. We talked about that, so I'll gloss over that. Keep learning. No matter how long you've been doing something, you can always get better. And for me, my goal when I get up in the morning is to never stop getting better. I want to continue to learn, apply what I'm learning, test what I'm learning, see what works, what doesn't. You know, some of the largest challenges we have as leaders is we use a script that works most of the time. But every now and again, we end up in a circumstance or a set of circumstances that that script doesn't work and we keep trying it again and again and again. Don't be afraid to try something completely different. Even if it feels awkward to you, makes you feel uncomfortable. It should be. That's what learning is about. You know, I used to lift weights, bodybuild, and I learned that the only way to build muscle and to get stronger was to tax yourself. And you get taxed to a point of being uncomfortable. You know, when you're doing a bench press and you're lifting that weight, you have a spotter. A good spotter is going to make you work for that rep. The same is the case in our professional lives. If you're building software, if you're building technology, migrating workloads from on-premise to the cloud, get comfortable with the uncomfortable.
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Steve Taplan15:07
Good advice. Very good advice. Last time I checked, the definition of insanity is doing the same thing over and expecting a different result.
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Rob Zelinka15:16
That's my definition.
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Steve Taplan15:17
So, I would agree with you. So, Rob, what is one brutal lesson or story you can think of that you wish you would have learned earlier in your career to help fast-track your success?
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Rob Zelinka15:28
Yeah. So, I've learned a lot of lessons. I'm, as I said before the podcast, I'm a work in progress. My wife will be the first to tell you that. I think the hardest lesson I've learned as a CIO is that clarity isn't kindness. And I teach my leaders who aspire to be CIOs, CTOs one day. I ask them a key question. Do you want to be liked or do you want to be respected? You can't be both. And of course, naturally, most people want to be liked. It's just human nature. The reality is clarity is our duty and responsibility. You know, early on I made the mistake of assuming that talent and good intentions would basically carry me through. In reality, I avoided those tough conversations early on and it did myself a disservice. It did the people I was leading a disservice. I was thinking that it was more important to be an empathetic leader than a real leader, a real human that gave you the straight and narrow that you needed. And that's where I learned the concept of feedback is a gift. You might not like the gift. You don't have to use the gift. You can discard it. You can vehemently disagree with it, but it's a gift. Someone has bestowed that on you and you can use it to prompt thought and challenge yourself. So, that was probably the toughest lesson I learned early on. And had I not learned that lesson, I don't think I'd be where I am today because, you know, our chairman of the board at Jack Henry taught us one day in a leadership summit that it's lonely at the top. And I didn't fully appreciate what he was saying. I heard it before, but the higher up you go, once you get to the C-level, it is lonely up there.
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Steve Taplan17:01
And I'll tell you, in the current age, it's a pretty tough job to be a CIO or CTO. Those are the people blamed for everything at this point. When we look at the average lifespan of CIOs and CTOs here in the past five years as we've been in the 2020s, I mean, I think the average lifespan is like 18 months. It's unbelievable. It's almost an impossible job. And it really takes the right people that have the technical knowledge and the business knowledge to be able to... it's certainly an art of being able to lead both non-technical and technical people.
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Rob Zelinka17:43
Yeah, you know you're exactly right. Someone had created a meme for me when I first became a CIO many years ago and it said 'CIO career is dead' or 'career is over', sorry. And you know, there's an element of truth to that, but I always rise to the challenge. You know, when we talk about being brutally intentional with ourselves, when we look ourselves in the mirror, you know, part of leading people is dealing with a bit of ambiguity, a bit of uncertainty, and that usually brings what I refer to as misalignment. So whether that misalignment is on your strategy that you're trying to drive for your business or whether it's cultural or personal personality-wise, as an old infrastructure guy, there are seven layers of an OSI model which you are keenly aware of. There's also an eighth layer. The eighth layer is the human layer. And so oftentimes the eighth layer is where much of the misalignment is because you have personality conflicts and there are people that come to the table having to win at all costs and then you have other people that try to find common ground. You'll never have the same type of personality at the table. The point being is you as the leader have to drive alignment as quickly as possible because in my mind leadership isn't just about vision. It's about making the uncomfortable decisions that will preserve the trust and move the mission forward. Because if you're not trusted, you will not be successful in your job.
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Steve Taplan19:13
What would you say, Rob, has been the absolute hardest part of being a tech leader, a tech exec, a CIO?
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Rob Zelinka19:21
I think the hardest part is seeing that this transformation that's occurring from a technology perspective is catching people off guard. And I refer to it as I can lead a person to knowledge but I cannot make them think. Ultimately they have to think for themselves. And so what ultimately ends up happening is people get caught flat-footed and they can't get their balance again and then they end up becoming casualties for whatever reason. I know those are strong words but it's the reality of the circumstance we face. Think of it this way. If you're a person that's been working for 25 years and you probably have another 10 or 15 years left, depending on your personal situation, you have to reinvent yourself so that you can continue to bring value to a company. And if you don't, you're going to be left by the wayside. You think of all the jobs that are at risk right now. It's crazy. And it's not just in the technology sector. Right now, logistics companies are running driverless semis from Dallas to Houston and Houston back to Dallas every day of the week. They're testing that technology. So, if you drive a truck for a living, you're under assault. You have to learn something new.
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Steve Taplan20:30
Tesla just rolled out their robo taxi in addition to Google's Waymo that's been out there, all driverless cars. It's definitely a fast-changing world and it's the same with technology. So, I'll speak to something that is near and dear to your heart. Let's say you're a software developer, a software engineer, and AI now can essentially do some coding. How does that affect your livelihood?
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Rob Zelinka20:54
For me, I would tell you to embrace it. I would tell you to use it. But what I would also tell you to do is trust and verify it. This is where the responsible use of AI comes in because we have seen epic failures with AI. Here's the reality. AI right now is plus or minus 95% accurate, meaning it produces a good outcome 95% of the time. Steve, would you board an airplane that lands successfully 95% of the time?
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Steve Taplan21:22
Hell no.
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Rob Zelinka21:23
Absolutely not. So that 5% is what is going to allow the human in the loop to drive that 100% or close to 100% accuracy better, faster, more consistently.
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Steve Taplan21:40
To that point, that's a great stat. You know, everybody in every role, whether you're a software engineer, whether you're a marketing person, no matter what you're doing, if you're not already using AI, you got to jump on the bandwagon because we have two choices here. You either jump on the bandwagon or you turn yourself obsolete. That's really the only choices right now. And as you brought up earlier, it's only going to be moving faster from here, not slower. So, it's definitely changing times. Well, Rob, thank you so much for getting uncensored with us today. Any final advice you have for tech leaders?
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Rob Zelinka22:16
Yeah. My advice is, and I alluded to this earlier, never stop learning. Come to work every day trying to get better. Don't get complacent. Don't accept your current state. Even though you've climbed that big mountain and you've looked down with fondness and appreciation, there's another mountain that needs to be climbed. And just keep pushing. And the more problems and obstacles you move out of your way, the more money you make. That's my two cents. Thank you so much.
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Steve Taplan22:46
That's it for this episode of Software Leaders Uncensored. I'm Steve Taplan. Stay bold and keep building, everyone. That's a wrap. Another great episode of Software Leaders Uncensored. Thank you guys so much for listening. I really appreciate it. It's a lot of fun doing this show. I love talking with great tech leaders. As a side note, if you're interested, check out my new book, Fail Hard, Win Big. This is the story of how I built 30 companies, failed on 20, and turned 10 into multi-million dollar wins. The common thread with all of them was custom software. Also, if you need software development help out there, my company, Sonatify Technology, we deliver world-class software development engineers out of Latin America. We have a solid track record of helping companies launch better products faster. Thanks again for listening. Appreciate it and appreciate you.