episode #42
From Apple Genius to Restaurant Tech Visionary: Kyle Mark’s JourneyIn this episode of Restrocast, Kyle Mark shares his journey from Apple to leading tech at WOWorks. He discusses fixing POS issues, scaling systems, and how COVID made tech a key restaurant driver. Kyle also talks about the importance of team alignment, smart integrations, and personal growth habits that help him lead with clarity and intent.
ABOUT THE HOST
Ashish is a serial entrepreneur and serves as the CEO & Co- Founder of Restroworks. He is one of the entrepreneurs who has mastered the art of bootstrapping startups to scale. Ashish is a prolific angel investor and mentors budding entrepreneurs and startups in Silicon Valley and India.
ABOUT THE GUEST
Kyle Mark is a seasoned restaurant technology leader with experience at Apple, Datum Technologies, Gecko’s Hospitality, and Ciccio Restaurant Group. Known for bridging tech and operations, he played a key role in supporting WOWorks through FTR Hospitality, where he helped scale and streamline multi-brand systems with a focus on integration, implementation, and business impact.
Speakers
Episode #42
In this episode of Restrocast, Ashish Tulsian sits down with Kyle Mark, a restaurant tech leader whose career has spanned Apple, various startups, and enterprise restaurant operations. Kyle shares how his journey started in Glen Ellyn, Illinois, took root at Apple’s flagship store, and evolved into a career transforming how restaurants use technology.
Kyle reflects on transitioning from Apple to the foodservice world through roles at Standard Market, Datum Technologies, and Fresh Kitchen—where he helped lead a rapid digital transformation just as the COVID-19 pandemic hit. He discusses how delivery became a lifeline, forcing restaurant tech to shift from cost center to growth engine.
Now leading tech at WOWorks, Kyle talks about fixing POS systems that weren’t set up well and how poor setup—not the tools themselves—is often the real problem. He explains that many failures happen because teams aren’t aligned. Kyle believes restaurant tech should work together smoothly, and that “best-in-class” means choosing tools that actually fit your business—not just the ones with the most features.
Find us online:
Ashish Tulsian – LinkedIn
Kyle Mark- LinkedIn
Ashish Tulsian:
Kyle, welcome to Restrocast.
Kyle Mark:
Thank you for having me.
Ashish Tulsian:
You know, I want to start with your Apple genius story. But before that, you know, tell me a little bit about where you grow up? How were the early years? And then we’ll get to how you become Apple genius before you got into the restaurant business.
Kyle Mark:
Sounds great. Yes. So I’m originally from the Chicago area. Born initially in Northwest Indiana, actually a town called Valparaiso, and then moved and grew up in Glen Ellyn, Illinois, west suburb of Chicago. Went to high school there. Ended up going to Western Illinois University. After Western, that’s actually when I moved to downtown Chicago, started working for Apple there.
Ashish Tulsian:
Did you study tech?
Kyle Mark:
I did. Yeah. Restaurant, or I’m sorry, computer systems. So, you know, state school, very basic computer systems. But that’s what I studied there. Yeah. So, I mean, grew up pretty normal, Midwest childhood.
Ashish Tulsian:
And then how did Apple happen?
Kyle Mark:
Yeah. So it was crazy. At Western, I worked at our computer book or school bookstore, specifically in the computer section. My boss knew I was leaving at the end of the year, and he had previously been a genius at an Apple store. And he was like, you know, you want to make a connection? I’ve got a friend, Joe. He’s a manager at the Apple store in downtown Chicago. He knew I wanted to live in the city. And I’m like, sure, that’d be great. And then later that evening, I was talking to my dad, and he’s like, oh, you know, do you remember so-and-so he worked with? And I’m like, yeah, you know, I remember. And he’s like, his son works at one of the Apple stores in Chicago. I’m like, oh, that’d be awesome, because I was a huge Apple fan, had been for years. He’s like, I’ll see if he can talk with you or anything. About two days later, I get a call. Number I didn’t know was Chicago numbers, but I answered it. And it was this guy named Joe. And he’s like, you know, it’s really weird. In the span of three hours, I got two calls from two completely different parts of my life about you. And it was the same guy. It was my dad’s connection and my boss’s connection.
Ashish Tulsian:
Oh wow.
Kyle Mark:
It was the same person. And so he was like, you know, when’s the next time you’re going to be home? I’d love to get you in. We’ll talk with you, see if there’s anything that works. And I was going home the next weekend. So I got into the city, went down, met him. And about two weeks later, had a job offer to start working at Apple in downtown Chicago at a flagship store.
Ashish Tulsian:
And what is the process of becoming a genius?
Kyle Mark:
So I actually started on the sales floor, you know, wearing one of the Apple shirts and selling iPods and Macs to people. And obviously I had a technical background and started troubleshooting at that source. Basically, they started with phones and iPods. They had a iPod specific genius bar. So I started working, just troubleshooting those. And then about a year in, I actually transferred down to Memphis. I met my wife in Chicago. She transferred to Rhodes University in Memphis, Rhodes College in Memphis, where she went, grew up and I followed. And when I got down there, a genius position opened and they knew I was very interested in that. So I actually went in and really great experience. When you become a genius at that time, at least I don’t know if it’s the same now, but they flew us out to Cupertino for three weeks and we did a really in-depth, hardcore training for three weeks, 10 hours a day in a classroom, wearing everything you can learn about Apple computers. So it was a really great experience.
Ashish Tulsian:
Interesting. Do you get teased by somebody in life for being a genius? Because the only reference I have for this, I’m a huge Big Bang Theory fan.
Kyle Mark:
Yes.
Ashish Tulsian:
And they had a segment on the show.
Kyle Mark:
Yeah.
Ashish Tulsian:
They really dissed the genius at the genius bar.
Kyle Mark:
Yeah. So if it ever comes up, my wife’s favorite saying is, it’s a title, not a description. And she, yeah, she does not let that go.
Ashish Tulsian:
I think you took it upon yourself.
Kyle Mark:
Yeah. It comes up more often than you’d think. So she really likes to poke it.
Ashish Tulsian:
So how long were you a genius?
Kyle Mark:
So I worked for Apple right at five years. After five years, my wife, she worked for Lifetime Fitness as a manager and ended up getting transferred to Chicago, back to Chicago. And at that time, I was actually really lucky. I’d been able to do what they call a career experience at Apple. And I was a new store opening mentor for their technical team. So I got to actually travel around, open up new Apple stores, train their genius teams, make sure technology was working in the stores. And at that point, though, Apple was smaller than it is now, but it was still a very large company. And it’s hard to kind of make a name for yourself, especially coming out of the retail ranks. And I decided to kind of see what else was out there. And so I had an opportunity at an Apple store in Chicago again to actually be a lead genius. The genius of all geniuses, right?
And I decided then, let me see what else is available. I put out resumes and filled out applications and got one call back from a little grocery store in the West suburbs called Standard Market. And they had one grocery store, I think four restaurants at the time, and they were looking for a store and restaurant systems analyst. It could be interesting. I mean, you know, I talked to them and went in, met with them. Kind of seemed really interesting. Ended up taking that position, was there for a while and actually opened up another grocery store, multiple restaurants. And that was really my first foray into restaurant technology.
Ashish Tulsian:
What was your first experience of getting into the retail and restaurant side of things, which was very different from what you were doing at Apple? So I’m actually curious on why did you take that assignment? But more than that, what was your first impression? You know.
Kyle Mark:
I think my first impression and the reason I took it, it was so different. Right. Like, I like to look at things as, you know, the kind of challenge it is. And it was going to be a whole new challenge for me. Right. It was something I wasn’t super comfortable with. I knew I could use some of my experience with Apple and just technology in general. But it was just something completely new, something I could learn. And that really was my like the reason I took it. And then my first experience was, wow, this is completely different. Because not only was it like, you know, retail and restaurant systems, but we had a corporate office. We had a corporate team. So I was managing like Microsoft Dynamics, which was completely foreign to me. Managing PCs because we had a ton of people on Macs, but a lot of people wanted a PC. I had never managed a Windows computer. I had been a Mac user for 12, 15 years. And so it was, that was foreign to me as well. So it was all about a new challenge.
Ashish Tulsian:
But were you the, like, was there a tech leader in that org you were working with?
Kyle Mark:
Yeah, so my boss, a guy named Ken Seng, who’s actually now with Science On Call. He was, he gave me my first job and he was over both marketing and technology. So he really kind of, you know, let me do as much in the technology space as I could, which was amazing. Kind of, you know, he didn’t let me just go free and do whatever I wanted. He was guiding there. But really giving me the space that I needed to grow and learn and make decisions. And honestly, make mistakes, right? I mean, that’s part of learning. So he was great at guiding me and helping me.
Ashish Tulsian:
I ask that question because, you know, one thing that’s really, I would not really say unique, but I think even more important in the restaurant as well as retail space is that, you know, most, almost, I mean, not almost, all of us are, you know, customers to restaurants and retail. And the problem is that everybody believes that they understand how it works. Because you experience it, right? For example, if I’m going to a, I don’t know, cloth manufacturing factory, I don’t know it, right? So I will go in with a mindset that, okay, I don’t know. I don’t know what this is. But for retail and restaurant, everybody on the street believes that they understand this. And that’s why they get into those businesses. That’s why, you know, people keep opening franchisees. And of course, it’s an effective business. I asked you that question because I want to understand what is your process to really understand the business before you can impact their tech decisions.
Kyle Mark:
Yeah. So, I mean, I have a little bit of background. I probably should have talked about this earlier. But I, you know, growing up when I turned 16, I started working in restaurants. I worked for, I scooped ice cream for a while. I worked retail. I worked for, you know, Kohl’s as a sales assistant or whatever. For summers during college, I’d work as a server in a restaurant. So I had, you know, a little bit of idea of how things work behind the scenes. Nowhere to the extent, you know, servers might not necessarily know exactly how the technology in the background works. They probably don’t know that, you know, a kitchen manager might have to take inventory, you know, on a certain schedule. So that for me was learning kind of that, you know, I had no idea what inventory meant for either a grocery store or a restaurant.
And they’re different, right? Like they’re very different. But like learning that and, you know, that was that was the biggest challenge really was getting over those preconceived notions of how it works. The POS, the front of house, you know, screens, even something like a KDS screen. That was easy because I’d seen those, I worked with them. But it was more of the back office systems and learning how really what the managers do and how they utilize those systems. That was the biggest hurdle for me to get over.
Ashish Tulsian:
Got it. And how long did you work for them?
Kyle Mark:
That was a year and a half, two years. I was telling someone earlier, we moved out, my wife got transferred to Chicago and I think it was 2013, 2014. It was the first real year of the polar vortex and all the cold weather coming down from Canada. I mean, and I had grown up in Chicago and I had never been as brutally cold as I was that winter. I mean, there were times where garage door froze to the ground. We could not open the garage door in the morning because overnight it melted off the cars, run down and frozen the garage door shut. Or my boss’s car, literally his diesel gas freezing.
Ashish Tulsian:
Oh, wow.
Kyle Mark:
Yeah. So my wife, about halfway through the winter, looks at me, she goes, I don’t think I can do this anymore. She’s from Memphis where you’re lucky if you get a snow day. And it was at that point, she’s like, we can’t stay in Chicago. I can’t do it anymore. We’d love it in the summer, spring, fall. Amazing. Winter was just horrible. So my dad and I had actually already been talking about it, but looking at actually becoming a franchisee of some business. And we did our research and we actually bought a franchise license for Jimmy John’s in Naples. And. We were like, OK, we can move to Florida. My parents lived in Florida, my dad and my stepmom lived in Sarasota. So we ended up moving down to Sarasota while we looked for a location to open in Naples and open our first Jimmy John’s. And, you know, I don’t know if you know of Naples, Florida, but it’s very old. There’s not a lot of new build.
It was very difficult to find a location that would work for Jimmy John’s. They have, you know, very specific, you know, square footage, ceiling height, frontage, very specific requirements. And it’s served them extremely well over the years. So I understand why it was just very difficult to find a location that worked. And I think there’s still only one Jimmy John’s in Naples at this point.
Ashish Tulsian:
Oh, wow.
Kyle Mark:
So we after a year, we decided. Maybe this isn’t for us. And we ended up selling back our franchise agreement and stayed in Sarasota. I actually, you know, I was working in a restaurant down there managing a restaurant and had met a family friend who owned a company called Datum Technologies. And they did outsource IT for restaurants. Went in, talked with him, and he knew I had restaurant technology background experience. So I started working for them as an account manager. And, you know, doing a little bit of technical support on the side, but really it was my first foray into kind of almost the consulting side of talking with restaurants that didn’t have necessarily an internal technology team. And working with their operations and marketing teams saying, you know, you should probably do this or let’s look at this POS. There was some sales aspect to it for sure. But I ended up working there and worked there for several years. They were purchased by a PE group and ended up leaving there and working for a group, more of a local chain of about 10 or 12 family sports bars called Gecko’s Grill and Pub in Sarasota. And that was my first, you know, I was head of technology for a brand, a small brand in Florida.
Ashish Tulsian:
How long did you work for Datum?
Kyle Mark:
I started working in 2015 and trying to do the math. My daughter was born right after I left, so about three and a half years.
Ashish Tulsian:
Three and a half. Working for a company that was outsourced IT team for the restaurants. And the fact that today you’ve, you know, panned a career where you are leading tech, you know, for a larger, you know, one now, we’ll get to that. When you look back, what was your experience? Like, what was the most interesting part of your experience at Datum?
Kyle Mark:
I think it was really kind of the, you know, spectrum of different businesses I got to work with, right? So First Watch was one of our base clients there. So, you know, technically table service, but you pay to register. Then we had, we worked with Earl Enterprises. They had, you know, Bucatapepa, which is a traditional table service to a sandwich, you know, order.
Ashish Tulsian:
They still have their own team, right?
Kyle Mark:
They did. We actually, it was, I was part of the team that we went in. We actually hired as part of the agreement, we hired their entire tech team into Datum and we took it over completely. And then after a few years, I had left Datum at this point, they transitioned back to an internal team. But we had taken over.
Ashish Tulsian:
I think Tom Seeker built that.
Kyle Mark:
Yes. Yeah. He came in. I had left Datum and he came in and took that back over.
Ashish Tulsian:
Got it. Yeah.
Kyle Mark:
But the whole, like the being able to experience table service, quick service, kind of a hybrid model, being able to see how all of these different, you know, restaurants, yeah, it’s all restaurant technology, but there is such a spectrum of technology for the restaurants, right? And, you know, that was probably the most interesting part. And seeing all company owned restaurants, franchise, that was my first experience working with franchisees. That was the biggest thing I could take away from working at Datum.
Ashish Tulsian:
Given the choice, you know, I mean, why not continue with a company like Datum?
Kyle Mark:
Even outsourced, you only have so much or especially outsourced. You only have so much say in what a restaurant group does with their technology. I have very strong opinions on restaurant technology, as I’m sure most restaurant CIOs do. And so it was one of those, I wanted to be able to not mandate, but I really wanted to be able to say, this is what we need to do. And this is what we’re going to do. I didn’t want to say, I didn’t want to try and sell it into a group that I wasn’t necessarily a part of, right? As much as you’re working with these teams day in, day out, you’re always an outsider when you’re doing outsourced IT, you’re doing consulting. I wanted to be able to be in that group where I was part of that real decision making team. And so that was really kind of my impetus for leaving.
Ashish Tulsian:
That makes sense. Yeah, I understand. I think, and that’s why I think consulting remains quite a, you know, not really a gratifying job for most. Throughout consulting, it doesn’t matter what industry you are in. You can’t really own the impact or you can’t really fully own the impact.
Kyle Mark:
Exactly.
Ashish Tulsian:
That’s fair. So then you went to Kecko’s.
Kyle Mark:
Yeah, I was there for until 2019. I had a friend who was director of technology for a smaller chain in Florida again called Fresh Kitchen. Amazing bowl concept. Build your own bowl, walk down the line, great food. He was actually leaving and he told their CEO, he was like, I’m leaving, but I have somebody I think you should talk to. And that was, I went and talked to them and I don’t, it was, I was there three weeks later. So it was a very quick transition, but it was great. We’re through the pandemic, which is when I started, I think, November of 2019 with Fresh Kitchen.
Ashish Tulsian:
Fresh Kitchen. And how big were they?
Kyle Mark:
Like, give me 11 units all over Florida. So three areas, Tampa area, Orlando, Miami area. And that was, you know, they didn’t have online ordering. They didn’t, they had just started doing some third parties. So it was an interesting time to get in that space. I was on a very rapid rollout of online ordering and integrating third parties and making sure that all worked. Luckily, I had started the process. I guess probably in January 2020. Yeah. So I wasn’t totally behind the eight ball and then middle of March happened.
And that was crazy because we hadn’t rolled out like Uber Eats or DoorDash. And we kind of, we kind of see a little bit that something was going to happen. And so we started those conversations with third parties end of February. So we were kind of ahead in the queue and we got them rolled out fairly quickly, you know, within a week or two after COVID actually hitting. And yeah, it was a really interesting time to be in that space with fresh technology that the teams hadn’t worked with. Our operations team wasn’t used to. And that was that went from being 0% of the business to 100% of the business within eight weeks. And just insanity.
Ashish Tulsian:
You know, while COVID was absolutely crazy time and I think, you know, nobody can look back and say, you know, any good thing about it generally. But, you know, for the restaurant technology space and for all technology people in hospitality, I don’t think there was a better time or better opportunity that COVID brought, which continues to roll today. And, you know, I see that technology in restaurants was not vestigial, but it was like, you know, just there.
Kyle Mark:
Yeah, it was.
Ashish Tulsian:
It was not at the center. It was not the core. You know, and I would I would actually just go out and say that technology did not have the seat on the business table.
Kyle Mark:
No, at the time, I think most technology groups and restaurants probably answered to the CFO. Right. It was a cost center. Absolutely.
Ashish Tulsian:
There’s no strategic value, at least being acknowledged.
Kyle Mark:
Yeah, I think I think really COVID absolutely changed the idea that technology. It wasn’t just something you had to have that, you know, the customer wanted sure it was something that you needed and could actually be not just a cost center, but a revenue center and something that would really help you drive sales. I think that was kind of a turning point for it. And probably at that point was like, OK, technology is elevated. They’re really part of the executive team there.
Ashish Tulsian:
So how did your understanding like when did it hit you that all technology is becoming strategic center? And that actually brings me to how did the transition from an 11 store, 10 store sort of place happen? You know, when to what?
Kyle Mark:
I will say I believe technology was should have been elevated much earlier when I was at Gecko’s, like I made that case. And luckily, the owners of that brand, like I think they believed it as well. And that’s kind of why they brought me in. They had originally been outsourced to Datum and they thought it was important enough to their business that they brought me in to lead their technology. So I firmly believe that technology was that important to restaurants. Yeah, it’s. I think, you know, COVID obviously cemented that in my mind. I believed it before, but it was really like, OK, this is clear and now it’s going to be clear to everybody. And I think without COVID, you know, that was obviously it was a major point for me being able to, one, learn a lot, you know, learning about what systems were best in class. You know, it was we were only as probably July, you know, four months in, three months in. And I knew immediately, like we’ve got to change online ordering platforms. We’ve got to have something where our third parties are actually integrated into the POS. Our teams aren’t having to work off four different tablets and enter them manually. And, you know. For restaurants, you know, margins are what they are.
Getting a, an executive team to, you know, invest in something where, you know, better online ordering our online ordering works right. You can place an order. Sure. But being able to, you know. Get them to believe that better online ordering that, yes, it’s going to cost more money, but it’s going to increase sales. It took me a while to learn how to actually I’m back in the position of having to sell it in. Right. I am leading technology.
I do have I’m a decision maker, but I’m not the only one. Right. And so that was a point for me to have to learn how to sell internally. Obviously, something that has helped me dramatically over the years, learning how to sell internally and make my case and use new data, which is extremely important for selling internally. But that was the biggest thing that I learned coming out of COVID. And what I think helped me continue on into, you know, going, like you said, from 11 to now, you know, 300 locations. So after Fresh Kitchen, I guess this was 20, 20 in 2021 has approached by actually the same. He had previously had founded Datum and he sold that. And then I left a few months after that. He had started a new group called FDR Hospitality, and they were doing outsourced accounting for restaurants. So, you know, he was in the restaurant space, the new restaurants. He saw that there was a need for accounting and Saladworks was one of their biggest clients. And I guess in his conversations with them, he realized they need technology help. They were a hundred units. They were running on, you know, poor technology, really bad, really bad.
Ashish Tulsian:
So you kind of joined them as a consultant?
Kyle Mark:
No, I joined FTR as an employee, but with Saladworks, which is now WOWorks, my current company. We were, they’re outsourced IT, right? They had one person internally beforehand for one person managing all their IT for a hundred locations. And they were buying two brands, Frutta Bowls and Garbanzo Mediterranean Fresh. So they were going to add another, you know, 60 locations, 70 locations on. And they were sold on outsourced IT and it was the right thing for them at the time. And so really quick at FTR, we built a team. You know, I think we had pretty quickly after I started, we had gotten up to like 10 people on the team. And we had a couple other clients as well, but Saladworks / WOWorks was really our bread and butter and where we kind of broke our teeth and we decided how we were going to do things. And one of the first things with buying additional brands, we had to decide, are we going to do a single tech stack, one POS, one line of work? Or we are going to try and manage multiple different systems?
And there were three brands at the time where we knew they were about to add a fourth with The Simple Greek, and we knew that there were plans in the future to grow and to get a lot more. And already on just those three brands, I think there were four or five POSs. And we knew then, like, we were a fairly small team at FTR even. It was untenable to be able to manage that for three brands, let alone if we wanted to get to five, 10, or 20 brands. And so we decided, let’s go with a unified tech stack.
And, you know, I was fairly hands-on, and talking to my guys that were really managing the database, and we said, it’s actually a really good POS. The database that had been built for Saladworks was what was killing them. And their franchisees were just extremely unhappy with the system. They had poor online ordering because they were using, I can’t remember the name of it, the technology.
Ashish Tulsian:
And franchisees were not happy?
Kyle Mark:
Not happy at all.
Ashish Tulsian:
Okay.
Kyle Mark:
And, but we, you know, working with it, we knew it was a good POS. And so we fairly quickly, a lot of late nights and all-nighters, completely rebuilt the database. And we rolled that out, and it was, I don’t want to say night and day, but it was a pretty quick switch of franchisees going from wanting to, you know, probably come through a Zoom call and kill us to loving us. Technology.
Ashish Tulsian:
What was the shift? What do you mean by, you know, changing the database?
Kyle Mark:
I mean, think of how Saladworks was a walk down the line concept, right? You go in, you walk down the line, you order your salad, you start with the base, toppings, proteins, modifiers. And the biggest choke point was the POS. And that was the backup. And you get a long line and people walk in, they see a line, that’s what they don’t want to see. Right? It’s not like, you know, order first, where you walk in, you order, and then you’re waiting, right? You’ve already given your money, you’re going to wait. If you haven’t given your money, you’re going to walk out.
Ashish Tulsian:
Yeah.
Kyle Mark:
Especially where restaurants, a lot of our restaurants are in strip malls, they’re surrounded by other restaurants, so there’s other options. And what we could do is get rid of that choke point, make it easier, make it work better, make reporting work. That was a major piece. The marketing team had a hard time telling, you know, being able to run a PMIX and being able to actually tell what was being sold and how to market things. So that was, you know, some of the changes we made very quickly, making it easy for a cashier to ring up a salad and say what proteins are on it and get the customer going, making payments easier, making payments faster.
Ashish Tulsian:
So you mean it was not the fault of the POS, it was just a poorly designed menu configuration? Exactly.
Kyle Mark:
Menu configuration, not just the menu, I guess, like, just the flow that a cashier and a customer had to go through, it was just inefficient. And we were able to fix that very quickly. I mean, even to the point where a franchisee would have a hard time 86ing an item, that was ironed out very quickly. And we figured that out. And that was that was really a turning point.
Ashish Tulsian:
That’s a very important point. I mean, I have seen that for a bit, you know, in our experience and, you know, and this is the first time I’m hearing it from somebody else. You know, it has happened with us multiple times while, you know, we kind of take care of it now. And we are quite sensitive to it, that menu configuration and, you know, how the workflow is done and how many steps does it have and, you know, what does a modifier versus an add-on, you know, what does it lead to in reporting and how does it, you know, impact your pricing and promotions. Yeah, we are extremely sensitive to that now, but we have seen, you know, that those slips where, you know, somebody at the implementation time on the brand side, you know, strong-armed, somebody on our side at implementation has said, hey, you know what, do it like this. And they said, sure. I mean, yeah, I don’t have the eligibility, you know, or the view into what’s your business call. And, you know, only later we, you know, somebody on our team realized that, oh, these guys are in a mess because they just went wrong with this one.
Kyle Mark:
And you mentioned operations. I’ll actually take one for that. I’ve personally seen a brand, I won’t say, but that marketing is really the one that’s driving their POS builds.
Ashish Tulsian:
That’s even worse.
Kyle Mark:
And it’s, they are extremely unhappy with their POS and I’ve told them like, you need to stop marketing from driving because they’re trying to basically, you know, shoehorn in legacy into what a new, they have a great POS new that should be able to work for them. But marketing is trying to turn it into something that they used to have and they’re used to, and they’re not willing to change. And that is ruining, and it will ruin any POS they have going forward.
Ashish Tulsian:
And I agree with you, I completely agree with you. But I, you know, I have, I really have, you know, a question here. I think in the restaurant space, and I’ll give you some context, I, you know, was a restaurant operator. And I was always a technologist, I used to run a telecom tech company. And I then became a restauranteur for a little while, less than two years. And so I experienced the heat, you know, that operator experience and then, and then being a restaurant tech company for 13 years now. And we’ve experienced, you know, some 20,000 plus restaurants. And I can tell you one thing that this best in class narrative for restaurant as a problem, I find it, you know, bringing more pain to the restaurant operators than the solution. And I’m, and let me, you know, also be specific in that, right. For example, there are a few things which are, which can be verticalized, like, for example, eCommerce. Okay. eCommerce is a consumer facing product stack. The job is to manage volumes, the job is to have a great UI, a great UX, fast checkout, you know, menu and what is being ordered, whether it’s soap or whether it’s a sob is the last problem. Right. So that is one class.
I understand that, right. But within the restaurant operations, what I have seen is that this best in class narrative has, you know, taken like really wild verticalization where features are becoming products where I see, you know, restaurant companies signing up seven, eight, 10, 11 different products of small and, you know, big size. And then they end up not talking to each other because integration is not only about talking to each other, what happens post integration, you know, does the architecture match, you know, is the data. And this is the biggest battle between front of the house and back of the house, which continues to remain unsolved in 2025. I’m yet to meet a restaurant operator, you know, and who will tell me that their back of the house and front of the house are absolutely in sync from, you know, making sense of the data and just not integration and, you know, reporting. So a longish question, but, you know, philosophy, where do you stand? And, you know.
Kyle Mark:
I think that’s my job. I think my job is making sure that they really communicate right. And when I say best in class, I don’t necessarily mean like there’s one product in each vertical that is the best in class, right? It could be the best in class for your needs.
Like, you’re not looking at a single item and saying they are the best, we’re going to go with the best one. I think there are, you know, there’s levels and I’m looking at like the best level, right? And not looking at, you know, somebody that, you know, did an online ordering system in their basement and threw it up for their mom’s restaurant. And I was trying to sell it, right? I’m like really best in class to me means it’s a great product. They have the team to stand behind it. Honestly, the money to stand behind it and make sure it stays a product that we’re going to be able to, it’s going to be viable for us to use for the next five years. And really my job then is to make sure that there’s that communication between the pieces that we put in place. Like you said, not just the integration, but working with my teams, my partners and connecting them also and saying like, hey, my POS, I really need you to work for my back office. Let’s find out why my data, my data is flowing, but it’s not working the way we need it to work. Help us out here, making sure they communicate.
If I do that, it’s probably going to help some other operators out there. But then if you look at, you know, you’re mentioning, you know, you’re signing up for seven, eight, nine, 10 items. A big part of that also is, you know, are you then paying seven, eight, nine, 10 bills every month? It becomes difficult, like tracking all that potentially becomes more expensive. I would argue that it probably keeps the cost down a little bit because…
Ashish Tulsian:
I think cost is just one element. I agree with the cost, but, you know, what I just said is the reason why, you know, let’s say some of the companies are now buying multiple products where, you know, the irony is, and it really beats me, their own acquired products are not really talking to each other seamlessly. Yes. And it’s not about technical prowess. They
won’t. They will never talk to each other. They may be able to, you know, kind of sync data through a middle layer eventually, but, you know, that’s not talking. That’s not a conversation, right? It’s like translating a French and a Spanish text to English. Yeah, you can probably do that, but that’s not a conversation. That’s not going to happen. Yeah.
Kyle Mark:
Yeah. No, I think, like you said, though, even as some brands acquire others, that’s not fixing it, right? And I think there’s also a downfall, though, if that of, you know, I’ll go back to POS, but if a POS company acquires an online ordering company or a loyalty company, it’s taking away focus from the product that they do best, or it potentially is, unless some companies are buying those. And like you said, the products don’t talk to each other, but a lot of times the product teams or the teams overseeing those products don’t even talk to each other.
Ashish Tulsian:
Correct. Correct.
Kyle Mark:
And so a lot of the…
Ashish Tulsian:
That’s worse.
Kyle Mark:
Yeah. And a lot of the implied savings of time and money, like, especially the time. Oh, okay. You’re both owned by giant company A. Great. I’m going to have one weekly call with you, right? Well, no, you still have to have a call with them and a call with us, our systems. Did we do this? Yes.
Ashish Tulsian:
Damn. I used to wonder. I didn’t know this. I used to wonder because I know that, you know, teams don’t talk to each other at a lot of places. So I used to wonder how our customers or account managers are fixing that.
Kyle Mark:
Yeah. We’ve used a POS that bought a loyalty company. And it’s like, your loyalty product doesn’t even work best with your POS. It works best with this other one.
Ashish Tulsian:
This is crazy. Yeah. This is my assumption. And it was my read. I never had a chat with anybody first-hand. We experienced exactly that.
Kyle Mark:
Yeah. And that it’s not any more painful than having, you know, separate things, but it’s mentally painful. You’re like, but you’re both the same company.
Ashish Tulsian:
That was the narrative that was sold.
Kyle Mark:
Yeah. And probably why the CEO of that giant company said, this is a great synergy. We’re going to work together. And it’s like, but you’re not.
Ashish Tulsian:
Back to your strategic side, what has changed for Kyle over the last, you know, let’s say four years, given you’re now having a seat on the table. Technology is at the center. You are impacting revenue as well as bottom line. You’re impacting new plans. I’m sure, you know, what is it like, right? Is it, has it changed already to the point where every new strategic direction at the company, you know, you are definitely in it given tech is going to lead it or enable it right from the start.NAnd how has that changed your understanding of what Kyle used to think in 2020 and 21 versus 2025?
Kyle Mark:
I think every major initiative that our company and probably most every other restaurant company handles right now. Technology is a key player. Right. I mean, for us right now, you know, we’re looking at how do we increase top line or, you know how do we increase AV in general and kiosk is a major initiative, right? Like, or, you know, if it’s, Hey, let’s look at back office. How is that going to affect our bottom line? Maybe not a top line or AV, but how is that going to affect margin and profit? And obviously technology, no matter where you look, it’s a key player in every initiative. And I think for me, what I’ve learned over the past five, 10 years is I need to know better the operation side, the marketing side, so that when I go and try and sell in a solution and talk about how the technology is going to make operations life easier or how it’s going to make it so that marketing can find, you know, a hundred new people per restaurant or like increase that top line. How are we going to find and market to our customers that we might not know? Like, you know, we have 17% of our customers in a loyalty program. How do you market to the other effectively?
And it costs efficiently. And for me having to understand how marketing works and what they’re looking at, that’s been my biggest takeaway over the past few years beforehand, it was, you know, I’m restaurant technology. I don’t care about operations and marketing and like, yeah, what I do, it does affect them, but they can come to me and tell me what they want. I feel like I have to be more proactive and say, here’s what we need to do. This is why it’s good for you operations. Let’s, let’s try this. Let’s, let’s talk about, you poke holes in it for sure, but I’m coming to you with a solution to a problem that I see you have. I don’t want you coming to me with your problems, asking for a solution and the same with marketing.
Ashish Tulsian:
So tell me a little bit about family. What’s happening on the personal side.
Kyle Mark:
So I’ve got, I’m married for 11 years, 11 years in May, and we’ve got two daughters, five and seven. It’s, you know, having them so close, they’re back to back grades. So weekends right now are full of birthday parties and soccer practice and soccer games. And um, if there’s none of that, it’s, can we go for a bike ride or scooter ride and go to the playground? So yeah, it’s a, it’s a fun time. It’s a busy, very busy.
Ashish Tulsian:
I’m on the way. I have a six month old. I know that there’s a lot of madness in front of me.
Kyle Mark:
Yeah. And uh, you know, my wife and I decided after our second, like that was it. We had thought about it, you know, third, but really it’s a, yeah. And our, our, her doctor told us we were thinking about it. He’s like, you know, with two, you can play a man to man. Once you go third, you gotta play zone defense. And uh, we’ve noticed where, you know, Hey, we can, if there’s an issue with between the girls or, you know, moody, we can separate them. My wife could take one, I could take the other. And it’s like, okay, let’s calm down. And we can go on a walk. I can go on with one of them, or she can take one to the store. And, um, once you get with three, that’s, that’s hard to do. So, uh, yeah, two, two little girls.
Ashish Tulsian:
And are you working from home or office?
Kyle Mark:
Yeah. So while it works, we’re a hundred percent remote. We don’t have no office. Um, our team is a hundred percent distributed in our executive team where, you know, CEOs in Naples are CFOs upstate New York. I’m in Memphis. Uh, my team, I’ve got people in Atlanta here in Vegas, um, New York, Delaware. So we’re all over the place down in Texas as well. And, um, so, you know, there’s pros and cons to being remote. Um, I wouldn’t trade it for the world. I love it. Um, you know, we are lucky enough where we still get together fairly regularly, especially as an executive team. Um, we meet up at least quarterly, but I feel for the past, you know, six months we’ve been meeting up every other month. Um, I find reasons to, you know, if I’m in an area that one of my team members lives, meet up with them for sure. So, um, you know, I think technology is another big piece in that, um, you know, we’ve implemented Microsoft teams, we’re a Microsoft shop. So, um, teams is a major piece for us. You know, there’s a, definitely a point where you have too many meetings, but then what we’ve started seeing is coworkers just having a video chat open. You’re not necessarily having a meeting, but having a video chat up and three or four people in there, you’re just working on your computer. You’re doing.
Ashish Tulsian:
Oh, wow. That happens that, oh, that I used to hear all about that during COVID.
Kyle Mark:
Yeah.
Ashish Tulsian:
But I used to be, I used to find it amusing. I mean, unnecessary those days. Yeah. I haven’t heard this happening now.
Kyle Mark:
Yeah. We, I mean, um, you know, my, the, my VP, he, uh, he and I will, you know, we’ll message him and be like, Hey, can I swing by your office? And I’ll literally just, we’ll start a team’s call and we’ll, you know, chat. And sometimes, you know, I’ve got, you know, something on my screen that I’m working on. And he knows that if I, my eyes gloss over for a minute, I’m looking at a screen that I’m probably reading something I need to read. You know, that’s, we’re not necessarily having a pointed conversation, but it’s, you know, we’re there, we’re talking to each other and it’s, it kind of gives you that social aspect back.
Ashish Tulsian:
But that’s a good culture as well. I mean, I think that that means, you know, you guys have a great culture for, for you to be able to do that.
Kyle Mark:
Yeah.
Ashish Tulsian:
What do you, what do you do to keep yourself enriched? How do you, you know, do you read books, podcasts? What’s what, you know, what, what happens? What’s, what are you doing for learning?
Kyle Mark:
Definitely read a lot of books starting last year. I hate New Year’s. I hate the term New Year’s resolutions, but it was kind of one of my, my personal initiatives, my personal goals to read more and not necessarily like I definitely read both fiction and nonfiction, but to start reading more professional development books and just for lack of a better term, self-help books.
Ashish Tulsian:
What are you reading right now? And what was the highlight of the year book?
Kyle Mark:
I think the, the book that made the biggest impact on me was the 5am club. I used to be a night owl. I would work late into the night. I would not like to wake up early in the morning. And I read that book and something clicked and
Ashish Tulsian:
Really.
Kyle Mark:
Yes
Ashish Tulsian:
I’m, I’m that guy you were explaining. So, yeah.
Kyle Mark:
And it’s, I’ll tell you as your kids get older, it’s more and more difficult to stay up late and sleep in at all because kids wake up early. Especially my kids were getting into school age. And so I was having to wake up every morning and get them ready for school. And I read that book and I don’t know what it was. It clicked in me. I’ve, there’s maybe a handful of days over the past year and a half that I’ve slept past 5am.
Ashish Tulsian:
Wow. And that is, that is nuts.
Kyle Mark:
It’s, I go to bed a little earlier for sure. But I feel better. I have far more energy. And it’s not just about waking up early, right? And it’s about what you do in the morning, how you spend your time, making sure it’s, you know, mindful and you’re doing what matters.
Ashish Tulsian:
I’m that at night, but that’s, that’s the point. I, I actually relate to nocturnal.
Kyle Mark:
Yeah, no, I, I was, that was definitely me. As winter 2023, like end of 2023, I was staying up late. I would, I would work late. You know, I had a habit. I still do this to a point, but I’d work during the day. I’d take some time off, spend time with the family, do dinner, get the kids to bed. I’d sign back on and I’d work late into the night. And now I still get back on after I go to bed, but it’s maybe the answer emails read through a few things. I limit my time. I find I’m far more productive in the days where I am working. Like my time is more productive. And in the mornings I wake up, I try not to look at a screen for two hours. I, you know, have a pretty set schedule of, you know, certain days working out certain days, just enjoying my time, drinking coffee, drinking water, being mindful of my time. And so I really, the 5am club was probably the most impactful book I’ve ever read.
Ashish Tulsian:
That’s amazing. I’m going to mark that for my reading as well.
Kyle Mark:
I highly recommend it. It is, I will say it’s a, the, the writing style is odd. It, it’s written as a fiction book. It’s not your traditional.
Ashish Tulsian:
It’s like a fable.
Kyle Mark:
Yes. Yeah. And you’re going to get me, you know, 10% of the way into the book and be like, what am I reading? and by the end it’s halfway through the book I was starting to implement some of the things I’ve already written and it was just I read that book I think in three days and it was just immediately life-changing.
Ashish Tulsian:
Awesome and what are you reading right now?
Kyle Mark:
I just finished Atomic Habits like on the plane right here.
Ashish Tulsian:
You’re on the spectrum.
Kyle Mark:
Yeah so I don’t know I’m probably going to go with a fiction book as my next book on the on the you know my next travels. Yeah I do a mixture of physical books, Kindles and audiobooks so I’m not sure what I might read next depends on what I have access to.
Ashish Tulsian:
That’s awesome. Kyle this was a great conversation and I don’t think I have ever discussed point-of-sale system or technology at all on this part in last part of our episodes with anyone in such detail but I think you know I love your thinking process. I think it was a great conversation. Thank you. Thank you for doing this.
Kyle Mark:
Thank you for having me.
Ashish Tulsian:
Thanks.
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