Tim Crawford: 0:05

Companies are looking for new ways to transform their business to remain relevant and differentiated within their industry. Technology now plays a central role in this transformation. Hello and welcome to the CIO in the Know podcast, where I take a provocative but pragmatic look at the intersection of business and technology. I'm your host, Tim Crawford, a CIO and strategic advisor at AVOA. This week I'm joined by Gaurav Singal, the Chief Technology Officer at Cantaloupe and formerly the EVP and CIO at the Georgia Lottery. In our discussion, Gaurav shares how his upbringing led to viewing life as an inverted tree. He talks about what it means and how it drives his optimism with technology. Gaurav discusses the importance of learning the business and how spending time with customer service and help desk teams can build insights. Garav, welcome to the program.

Gaurav Singal: 1:02

Yeah, thank you, Tim. I'm happy to be here and share my thoughts.

Tim Crawford: 1:07

You know, I'm really excited that you're uh joining the program and looking to dig into this conversation. So you're the chief technology officer at Kantaloop. You're formerly EVP and CIO at Georgia Lottery, VP of Tech at Goldman Sachs. I mean, quite a storied background. But maybe to get us started, tell us a little bit about yourself and your role as CTO at Cantaloop.

Gaurav Singal: 1:33

Yeah, for sure. Yeah. Thank you, Tim. I currently am the chief technology officer at Cantaloop. You know, I grew up as a technologist. I'm a software engineer by heart, and I've been in the industry for a little over 25 years, right? I love technology. I like to live, breathe, you know, drink everything, and very passionate about technology. From a personal side, I live in um near Brookhaven in Atlanta, married to a beautiful wife who's a professor at Emory. We like to spend time and socialize with friends in our free time.

Tim Crawford: 2:10

In our conversations, you just exude technology. If you could tell this is a passion of yours. But I want to kind of dig into your background a little bit and help the audience kind of understand a little more about who you are. And I think, you know, as we were kind of talking through your background and your history, that's kind of shaped your thinking. Let's understand a little more about your upbringing.

Gaurav Singal: 2:34

Tim, I uh grew up in a middle class family in India. My dad was a professor. You know, I'm eternally grateful to him. He exposed me to technology and computers at a very early age. So at the age of 13, he was a professor for mechanical engineering, and I was doing some CAD drawings for him so he can show his students how you know the models look like on a computer and in a 3D image. So that really sparked my interest in technology. You know, I started very early, started programming in COBOL and Pascal, which is like you know, the dial phone. You know, some of the generations may not know about that today. But that's how I started. That was an early preview for me in computers, in like, you know, 3D modeling, in programming. And since then, I've been in computers. I did my computer science. And then also, as a part of my career, I've been having growing roles across investment bank to logistics to gaming to fintech.

Tim Crawford: 3:36

Love that. Love that. And I think that kind of speaks to who you are and how you also think about technology. And we're going to get into kind of your thoughts on technology in just a couple of minutes. But one of the things that you mentioned to me is that when you look at life, you look at life as an inverted tree. Can you kind of walk us through what that means to you and what that looks like?

Gaurav Singal: 4:02

Tim, as I was saying, your life as well as your career is like an inverted tree, right? You start at the root, maybe your first job, maybe your first career, your degree, or even just any kind of a curiosity, right? As you grow, as you actually make progress, right, the branches, like how the branches of the tree fan out in different directions, right? Similarly, every branch in your life, in your career, represents a different role, a different industry, a challenge or an opportunity. Right? Some may feel it's straight, some may feel it's a little stable, some may twist unexpectedly, or it may lead to something new, right? But you're not stuck, right? You have options, right? You can climb up, you can climb down, right? You can go sideways, or you can go back to something you may have missed, right? And there's no right or wrong branch. And you know, at different points in your life, in your career, you just look at what's right for you, and then you actually take that trajectory for you to grow. And the higher you grow in that tree, right, the broader your view becomes. So that's how I look at life as an inverted tree.

Tim Crawford: 5:18

Hence the inverted tree. You kind of start at the top and work your way down in some ways.

Gaurav Singal: 5:23

Yeah.

Tim Crawford: 5:23

Is there ever a time when you go out one branch and go, ooh, this is not the right branch?

Gaurav Singal: 5:29

Yeah. Need to go a different direction. And again, you know, I know Amazon talks about it, right? Like, especially in they said there's always a decision that also is a two-step decision. If you've taken a decision and you realize that, hey, by the way, this is not right, you should be welcome to go back, step back and change and take the other decision because there's no point throwing more money or bad money after bad money. Bad money after bad money, sunk cost is sunk cost. So that's how I think about decisions as well.

Tim Crawford: 6:00

No, I love that. You know, I think it's interesting how your upbringing and how that's influenced who you are, but also how you think. Let's kind of move to talk a little bit about technology for a minute. You mentioned earlier in the podcast that you were excited about technology. And one of the things that you've mentioned to me is you're an optimist when it comes to technology.

Gaurav Singal: 6:24

Yeah.

Tim Crawford: 6:24

What do you mean by that? And how do you think about the balance between both optimism, but then also risk?

Gaurav Singal: 6:31

You know, I've been uh in a lot of different organizations, right, as a part of my career journey. And I've seen a lot of times, especially in IT, right? I have heard even CIO being CI no, where uh people would be like, hey, no, we can't do this, we can't do that, right? Too risky, too costly, don't have time for that. We are very busy. So I always look at it as you can, as a leader or you as a technologist, you could look at risk all day. But at the very end, right, if you're a technologist, you need to show the art of possible, which is essentially is like, hey, let's try, right? Let's try and see where this takes us. And that's always has been my philosophy in order for me to make an impact in the business. Because when you're trying, when you're an optimist and you see the art of possible, you make an impact about to the business. But also, right, to your point, looking at risk versus optimism, right? You also has to balance what that risk is about, right? If it is a risk and compliance in your business, then you should always pin that risk to the top and be able to evaluate and do something so that your business is not at the wrong side of the law, right? So there's definitely a fine balance between looking at risk, what it means from a compliance or regulatory perspective, and then also optimism from a perspective that, hey, let's show the art possible, let's see what we can do together versus analyzing risk all day.

Tim Crawford: 8:06

No, I love that. And it's kind of counter to how a lot of folks think about IT organizations as the department of no. I know this is something that we've talked about in the past. Is this really a way to maybe get beyond that and start to change that perception?

Gaurav Singal: 8:24

For sure. Yeah, for sure. You know, I think when you start partnering with your business partners, right, and we when you become a person of yes, right, or a person of optimism, more and more you will see the folks across the organization coming to you, you know, and that's a good problem to have. Yeah. Versus, you know, being rather than the CIO being called as a CI no.

Tim Crawford: 8:48

No, I love that. I love that. You talk about business, and you know, one of the things that we have to do as IT leaders is find that connection between what we do as IT leaders and how that interacts with the overall business. You know, you've talked about the importance of learning the business. What do you mean by that?

Gaurav Singal: 9:12

So it's very important, Tim, as a leader, as even a software engineer, right, is to understand the business, right? Understand your customers and then fit technology in between, right? Because, you know, if I'm the superstar engineer, super smart software writer, right? I would be just refactoring my code and making it look nice and awesome and be pivoting on new technology. What I learned early in my career is at the end of the day, we are in business. We are in business to serve our customers, right? So it's very important whenever I start somewhere, right? And even during the course of the year, I spend my time in the call center. I spend time with our sales organization as well as account executives because you know the people who are interfacing with the customers, right? The folks who are making a living selling the product that we have written, it's very important to hear from their perspective as to how our products are doing. And I always believe even if there is one call that is coming in the call center, there is something that you can do in your system better. So I treat that as a defect or a bug for every call coming in the call center. And I always encourage my team members to spend the time in the field, talk to the frontline workers and be able to understand what they are doing in and out, how our software, how our IT is doing. Those roles are very hard, right? Those are the frontline. It's important to have that empathy and be able to kind of learn the business and be able to build on things that can make an impact.

Tim Crawford: 10:52

No, I think that's really important. And actually, one of our fellow CIOs walked us through how one of his requirements with new leaders on his team is they need to spend time in the call center. They need to spend time on the help desk. It's something that the people fight and push back on. Yeah. But it's also a great way to truly understand what's working and more importantly, what's not working, and give them kind of a direct view into the customer's eyes.

Gaurav Singal: 11:24

For sure, Tim. You know, and I have actually over like at different places in my career, I have actually grown uh folks in customer service or help desk to the role of QA. And then from QA to role of product to becoming like a senior product lead to a chief product officer at different organizations. So I feel like people who are close to the customers, they understand the business, they understand what the needs are, and they actually grow really rapidly if they are intellectually curious and that's something they want to do. Yeah. Also, Tim, I think I I've also seen that oftentimes as technologists, right, we like to do technology for technology's sake, right? We will uh build some things which are bright, shiny objects, but at the end of the day, right, if those things are not used, right, if they're not generating a revenue, they are not getting adopted, they are useless, right? So I have seen that multiple times in my career where technology and business are not aligned. And it is very important to have that business discipline to be able to make an impact and be able to build things that our customers and our business finds value.

Tim Crawford: 12:37

I think that's incredibly important. And it's something that comes up again and again in conversations is where's the value? There's this belief that there would be value in building something, but it doesn't necessarily pan out that way. And one of the ways that we're seeing it today is with AI. And the studies, the surveys that are coming back are actually proving this out that folks are starting with really good intentions, but the ROI is just not proving out. Kind of curious your take on AI and where that fits into this conversation on value and building things that might not end up getting used.

Gaurav Singal: 13:16

Yeah, no, I think first of all, right, from an AI perspective, I think that ROI on AI is still yet to be determined because I think there's a lot of experimentation. A lot of people are actually playing around with AI. You know, I always look at you know, any technology advancement I look at as like, hey, what I'm doing in a day, can I do it in an hour? What I'm doing in a week, can I do it in uh in a day? Right. And AI is enabling that, right? There are certain things, right? If you're a data analyst, right, you're going to a website, downloading a file, and doing some analysis, right? You could do that. It will take you an hour or a day, but with AI, you have an ability now to do that more efficiently in less time. So definitely AI is providing some good value and efficiency. I think the unit cost of doing a thing is definitely, I feel, and I see that it will reduce. But some of that efficiency will erode, right? Because now you're doing some other value work for the organization, right? So I do think the total impact of AI is still yet to be seen. But I do think in a few years, five years from now, how we operate as individuals, how we operate as technologists or business people, it would be definitely different than what we do today.

Tim Crawford: 14:37

Yeah. If you look back on where you and I both started in our respective careers and how we've traversed our career history and where we are today, a lot has changed. And I'm kind of curious as you've as you kind of think back and go, okay, if I knew then what I know now, yeah, what would you tell your younger self that would be beneficial?

Gaurav Singal: 15:02

Yeah. So I think one is technology is uh team sports, right? Like what I love to tell myself like 20 years or 25 years ago when I started my career is like, hey, you know, how you have played sports in your college or as a kid, right? Even in business, right, there is no technology for technology's sake, right? It always is business first, actually, customers first, then is your business, and then you fit in technology. But also, right, like you're not as a software engineer, right? If you just write code all day, right, and it, as I was saying, if it doesn't get used, there's no value. You have not created the value. So it's very important that what you have done is also aligning with the business partners to show them what value it has created, and then to make sure that it actually gets deployed or used by the customers or by the business, right? So that is one thing that I would like to say is the learning is always play sports or technologies at team sports. Secondly, I think I have learned more in my entire career versus at school, right? So I always like to say that I'm a lifelong learner and I wish I could even learn a lot more things early in my career and be positioned for more success. If I had more time, I would have read more books or seen some more YouTube videos. Another advice to my younger self is be intellectually curious, be a lifelong learner, and continue to see what a new technology or what whatever interests you, you know, try to dig in, try things.

Tim Crawford: 16:45

Yeah. No, I love that.

Gaurav Singal: 16:47

Yeah. And then again, you know, this is a journey, right? Like your career is a journey, right? And it's there's no not a milestone. There's not you're stopping somewhere. And the same thing is in business, right? We are all transforming while we are performing, right? What you see in your business today is perhaps the worst that you will see because your tomorrow is going to be better than today, right? And that journey always starts with you.

Tim Crawford: 17:13

Yeah, no, I love that. And curiosity is something that comes up again and again. It came up in one of our last episodes with Cindy Stoddard, the CIO of Adobe, talking about the importance of curiosity as a trait of an IT leader. One thing I did want to kind of double-click on and ask you about is, you know, when you think about resources that someone coming into the space or the next CIO or CTO coming up through the rank and file, what are some of the ways that they could take advantage of where they are today? Are there things that kind of stuck out that you would kind of look back as you were maybe one step or two steps behind where you are today, that you would go, gosh, I wish I would have done this or maybe encourage someone to do something different?

Gaurav Singal: 18:01

Yeah. Like, you know, I think we kind of talked about a little bit earlier today. One is, you know, as a CTO or CIO, everybody I in the C level suite, I call them chief uh value officer, right? You need to create that value. Another chief officer title, right? CVO. Yeah, CVO.

Tim Crawford: 18:19

Heard here first.

Gaurav Singal: 18:22

Yeah, and it's important, you know, to be that person of yes, right? Is like, hey, let's look at it, how we can do this together and how we can create value. I think that is very, very important as a chief value officer, as a CEO, as a CTO, and CIO.

Tim Crawford: 18:39

No, I love that. Love that. Heard here first, chief value officer, new title coming to the C-suite near you. So as we kind of wrap on the episode, yeah. I always like to ask this question of my guests, and this is absolutely one of the best times to be a CTO, be a CIO, an IT leader. But you having that experience of having been both a CIO and now a CTO, I'm curious, like, what's exciting you most about the role and where technology fits into that if it does? Or is it might be about leadership, it might be about people, it might be about other aspects. I'm just kind of curious, like, what's getting you excited these days?

Gaurav Singal: 19:24

Yeah. For sure. You know, when I look at uh CIO role, right, it's about running the business seamless and flawless and making sure our internal processes and internal systems are running and providing efficiency. And as a CIO, at least what I've seen is you are in a lot of companies seen as a cost center or as a as an expanse. And the way you make an impact is actually at the bottom line, where you make an impact at the eBeda, where how you can run things efficiently, how you can bring productivity, and you need to be on top of it and talking to different. Internal stakeholders versus in my CTO hat, right, it is all about building the future, right? Building the future of the products that our customers use. So that way they can be more efficient, they can make more money. And it is about essentially like external facing, right? This is essentially when I am as a CTO, I see how I can make an impact on the top line. And that's a very interesting conversation I have with my CFO is like, if I'm running under my budget as a CTO, right? I'm getting a call, it's like, hey, you're not building the future. What's wrong with you? If I'm a CIO and I am running over budget, it's like, hey, what's wrong with you? You need to be under the budget, right? So that's a fine line that over a period of time that I've learned that, hey, this is a fine distinction between CTO and CIO. But what is important between these two roles is technology, right? Like I look at different trends, I look at what's happening in the market and how those technology, those software, any partnerships we could do with startups, etc., how we can either partner for our products or we can actually bring in-house that can bring that efficiency or make an impact either internally or externally to our customers. So I feel like there is a fine distinction between the two roles. But at the end of the day, if you're intellectually curious and you see technology, there is kind of a similar use where you could make an impact either externally or internally.

Tim Crawford: 21:37

Love that. We're gonna have to leave it right there. Gaurav, thanks so much for taking the time today and joining the episode. For sure. Thank you, Tim, for having me here. For more information on the CIO in the know podcast, visit us online at CIOinthenow.com. You can also find us on Apple Podcasts or wherever you listen to your podcast. Please subscribe and thank you for listening.