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How Shipley Donuts Built a Modern Tech Stack from Scratch

Transcribed Jul 14, 2026
Intermediate 5 min read For: Restaurant operators, franchise executives, and technology professionals interested in digital transformation in the food service industry.

AI Summary

Kerry Leo, VP of Technology at Shipley Donuts, discusses the 90-year-old brand's digital transformation journey, from minimal tech to a cloud-first, mobile-first infrastructure. He shares insights on evaluating technology, implementing AI for ordering and franchisee coaching, and the importance of solving real operational problems.

[00:00]
Shipley Donuts Background

Shipley Donuts is a 90-year-old brand based in Houston, Texas, known for warm-glazed donuts and kolaches. It started in 1938 selling a dozen donuts for a nickel.

[01:30]
Tech Transformation at Shipley

Kerry Leo joined Shipley in 2021 when there was very little technology—just cash registers and QuickBooks. Over five years, they rolled out POS, back office systems, online ordering, and a mobile app.

[03:00]
Career Path into Restaurant Tech

Leo started in technology after a music career, working at a company that provided POS systems for retail and convenience stores, then moved to Chick-fil-A to bring POS in-house.

[04:30]
Why Shipley?

Leo was attracted by the nostalgic brand and the rare opportunity to build a tech stack from the ground up, focusing on cloud-first, mobile-first, and secure platforms.

[06:00]
Growth and Franchise Model

Shipley has about 385 locations, aiming for 400 this year, with a goal of 750 by 2030. They have 12 corporate stores used for testing, and are expanding eastward into Maryland, Virginia, North Carolina, etc.

[08:00]
Evaluating Technology Partners

Leo starts by visiting shops and talking to franchisees and cashiers to identify pain points. He focuses on solving problems rather than adopting tech for its own sake.

[09:30]
AI in Online Ordering

Shipley partnered with Savory to improve online ordering. AI suggests upsells, knows when a customer is near a dozen, and can build large orders for parties in seconds.

[11:00]
AI for Franchisee Coaching

Shipley sends a monthly 'Donut Dashboard' to franchisees, analyzing data from their data lake to identify opportunities to increase sales, reduce costs, or manage labor.

[12:30]
Personal Tech Stack

Leo uses an iPhone (still on iPhone 11), prefers Microsoft over Google, uses Teams for communication, and likes Claude among AI tools. He uses Google Maps and the music app Museo.

[14:00]
Future Plans: Voice AI

Shipley's mobile app will soon include voice AI, allowing customers to order via Siri while driving.

Shipley Donuts is leveraging modern technology and AI to enhance both guest and franchisee experiences while preserving its nostalgic brand heritage. The company's focus on solving real problems and building from the ground up positions it for continued growth.

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Study Flashcards (6)

When was Shipley Donuts founded?

easy Click to reveal answer

1938.

What was the initial tech stack at Shipley when Kerry Leo joined in 2021?

easy Click to reveal answer

Cash registers and QuickBooks.

01:30

How many locations does Shipley have and what is their 2030 goal?

medium Click to reveal answer

About 385 locations, aiming for 750 by 2030.

06:00

What is the 'Donut Dashboard'?

medium Click to reveal answer

A monthly AI-generated report sent to franchisees that analyzes data to identify opportunities to increase sales, reduce costs, or manage labor.

11:00

Which AI tool does Kerry Leo prefer for personal use?

easy Click to reveal answer

Claude.

12:30

What feature will Shipley's mobile app include in the future?

medium Click to reveal answer

Voice AI ordering via Siri.

14:00

💡 Key Takeaways

💡

Building from the Ground Up

Demonstrates the unique opportunity to create a modern tech stack from scratch at a legacy brand.

01:30
⚖️

Problem-First Tech Evaluation

Highlights a practical approach to technology adoption focused on solving real operational issues.

08:00
🔧

AI-Powered Upselling

Shows a concrete example of AI improving online ordering and increasing average check size.

09:30
🔧

Data-Driven Franchisee Coaching

Illustrates how AI can support franchise business coaches with actionable insights.

11:00

✂️ Creator Tools: Viral Hooks

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Lawrence Shipley, I think in 1938. Yeah. It's just a family in Houston that started up. And I think back then they were selling a dozen donuts for like a nickel or something like that. I'll make that deal. How about you, Utavich? You make that deal? I'd make that deal. I don't blame you. Damn good deal. Welcome to Restaurant Influencers presented by Entrepreneur. I'm your host, Sean Walcheff. This is a Cali BBQ Media production. We are coming

to you from the Restaurant Franchise and Innovation Summit in San Diego. And the coolest thing about this show is that the level of talent, restaurant leadership that have come to this show all over the country. And we have Kerry Leo. He is the CTO. Well, not yet. Not yet. I'm the VP of technology. VP of technology at Shipley Donuts. In life, in the restaurant business, and in the new creator economy, we learned through lessons and story.

Carrie, I heard you speak at Murtec, another technology conference that we went to. We care so deeply about the restaurant business, the technology industry, how it intersects with restaurants, and obviously we care about storytelling. So we're grateful to have you on the show. Can you high level what's Shipley? How big is the brand? How long have you guys been around? Shipley Donuts, based out of Houston, Texas, is a 90-year-old brand. The best donuts you'll ever eat

in the whole world. If you haven't had one, you've got to stop and get one. The warm-glazed donut is the best thing. They also, Shipley has kolaches, and a lot of people don't know how to even pronounce it, but they're great. They're kind of from a Czechoslovakian. Vakian background and so really delicious food. I came out from Atlanta to Shipley back in 2021 and there was very little tech there. So really just cash registers and maybe

QuickBooks. That was about it. So we had a lot to do over the, we've done a lot over the last five years of rolling out systems, POS, back office systems, online ordering, mobile app, all that stuff to kind of bring Shipley to the current state of what's going on in the restaurant business. How long have you been working in technology? Gosh, going on 23 years, I think. 23 years. What brought you in? What was the moment

where you were convinced? Yeah, the moment. So it started in Atlanta and I kind of wanted to get into technology. That's how I got into it. I was doing various other things. I have a music background. I was trying to be a rock star back then and all this stuff. You're still a rock star. You're a Donut rock star. Donut tech rock star. Donut rock star. Yeah, Donut rock star. But yeah, playing music. I was like,

okay, that's not going to work out. Yeah. I started at a company that did software and hardware manufacturing for retail and petroleum convenience stores and food. And so that's how I got into it and happened to be on the team that was launching a new point of sale system to some pretty big brands like Chick-fil-A and whatnot. So that's how I got into it, just supporting it really and then became a systems engineer, so setting up

configuring the systems. Chick-fil-A brought me on to help bring a lot of that kind of stuff in-house for the point of sale side of stuff. And from then, it's just been this ongoing journey. What about the Shipley story? What convinced you that you wanted to work for this brand? For Shipley? Yeah. It's very interesting. When I came out for interviews, I just saw this nostalgic brand with a delicious product. and it was one of those rare

opportunities for a technologist to come in and build something from the ground up. I had been at other brands prior where they already had an old tech stack, wanting to transform it, move more digital, but with Shipley, it was literally building it from the ground up. So it was really exciting to come in, clean slate, and be able to just put everything you need and so we focused on being cloud first, mobile first, all the things

that anybody would ever want to do. Very secure platform but very set up to where operators could just operate from their phone or from tablets or whatever. You didn't have to have a lot of maintenance on servers and you know, have to be in the shop doing stuff or in the restaurant. So that's what really excited me about coming out. How many locations? We are at about 385. We're probably going to hit 400 this year, which

will be a big milestone. In the pipeline, there's a couple of hundred more coming. We hope to probably double in size, I think, or get close to it. By 2030, we'd love to be at around 750 or so. Amazing. That's incredible. Franchise model? Franchise. How many corporate stores? Yeah, we have 12 corporate. Okay. And we use those to test a lot of our stuff, and it's fully loaded with all our tech stack. Franchise, mainly, and we're

growing into new markets. So if anybody's interested, it's really a good investment. We're really growing more toward the east. So since we're centrally based in Texas, that's home base. But we're growing. We're now in Maryland, Virginia, North Carolina, Alabama, Georgia, Florida. So we're moving out toward the east. We are kind of looking at some of the states, not quite in California yet, but Nevada and I think New Mexico as well. What does a typical store look

like? How many square footage? Is it drive-through? Yeah, most of the ones, most everybody wants a drive-through. And I'm not sure of the square footage, honestly. I'm afraid to say because I'll get it wrong. That's right. But yeah, most have a drive-through. Our shops are really laid out where it's old school. They make the product fresh every day. in the back, literally the bakers come in, make everything from scratch every day. And so the donut rack

is full. It's very colorful. Everybody shops with their eyes. So once people get to know the brand, the drive-thru really picks up. Like in Houston, drive-thru's a big deal. Some of the newer markets, they like to go in and kind of see what we have, right? And so it's one of those things where drive-thru's super important. We're working to really speed that up as well. And we're continuously innovating even with AI and things like that to

make the guest experience better and make make the operational experience better for the franchisee. Did you know that Toast powers over 140,000 restaurants across the United States, Canada, and UK? It's an incredible company. I'm on the Toast customer advisory board. They are proud sponsors of this show, Restaurant Influencers. We couldn't do it without their support. They power our barbecue restaurants in San Diego. If you have questions about Toast, if you're thinking about bringing Toast on to

be your primary technology partner at your restaurants, please reach out to me. I'm happy to get a local Toast representative to take care of you. You can reach me at Sean P. Welcheff on Instagram. Once again, thank you to Toast for believing in the power of technology, the power of storytelling, the power of hospitality. Back to the show. When you're evaluating technology brands that you're gonna work with, what kind of filter do you go through? Yeah,

first, the first thing I do is I love to go to the shop and I like to talk to the franchisees. I like to talk to the cashiers and find out what their pain points are. That's the starting point. And then internally, we talk about it with our ops team and marketing team. What problems are we trying to solve? I've never been one just to go get tech for the heck of it and say, oh, they're

getting new tech. We need to get it. We want to solve problems. So what we've been able to do, is we evaluate that first. And then shows like this that we're doing, Mertech, FSTech, other shows like that. I talk to a lot of different companies, a lot of partners, and what's on their roadmap. We do evaluate, we want to know that they're investing in the automation and things. Restaurants are hard. You've got restaurants. I have three

restaurants. Yeah, you've got restaurants. So how do we make it easier? How do we make it easier for our guests to, one of our latest things, we partnered with a company called Savory. And online ordering was really clunky for donuts because they have to, historically, okay I'm gonna get a box of donuts and you pick a box and you had to fill the box up one donut at a time. With Savor we were able to solve

this problem that just dropping donuts into the basket and it knows when you're at a dozen and gives you a discounted price. It also knows when you're almost at a dozen so if you get the 10 to 10 donuts it will suggest hey For another $1.50, you can get a dozen and get the discount. It will also suggest upsell like a great cashier would do. And so it knows, and we also have, we had it originally

named, I can't even say the name, but it was something bot, right? With dough in it. So we, with AI, it's learned like what are the most popular donuts everybody's selecting. And so for large orders, you can just put in there, I have a party for 50 people. And it will build the order, kolaches and donuts, within about 10 seconds. And that's really been great for businesses. We have a lot of businesses that order from us.

Bigger check we're seeing with that. And then also with our franchisees, we've implemented AI to... help the FBCs. I don't know if y'all have franchise business coaches or that model, but they've got a lot with getting around all these shops. So once a month, we send out what we call the donut dashboard to every franchisee for every shop. And it actually is looking at all the data points we built in our data lake, and it lets

them know some opportunities they have to increase sales or to reduce costs or manage labor better. So it's actually evaluating and kind of being a coach for the FBC so they can sit down and have a great conversation with them. That's amazing. What's the origin story of Founders Shipley? Oh, great, great story. Lawrence Shipley, I think in 1938. Yeah. They were, it's just a family in Houston that that started up and I think back then they

were selling a dozen donuts for like a nickel or something like that. But the family is still part of the business. Oh, how cool is that? And they have shops and it's great to talk to them and hear the stories. So a lot of them are very involved. They come in and talk to us, but they run shops still still. So it's really a great family. a great product and if you're ever in the Houston area

because it was kind of born there, it's a staple event or a place to go to for everybody that's ever grown up in Houston. I grew up in Georgia so I didn't know a lot about it but I can't tell you how many times I'm walking down the street and they go Shipley, you work at Shipley and I hear all the stories of them growing up in the shops and their mom and dad taking them there,

and they're taking their kids there now, so it's very generational. I think it's one of the most rewarding parts about the business, just having our restaurant for as long as we have, having other generations come in and bring their kids in, and when you have a brand that's operated as long as you guys have, I'm sure the stories are just so amazing. Yeah, when you think about 1938 and what all's happened between then and then. I

mean, there's a small list of brands that have survived that long, especially in the restaurant space. Right. Yeah. That is really cool. One of my favorite things that we do on this show is we talk about your personal tech stack. So I would love to know, are you an Android or iPhone user? I'm an iPhone user. iPhone. Which version? I'm kind of a late, I think I'm still on 11. You're still on 11. Yeah. So when

do you decide to upgrade? I held on to a 4. I held on to a 4 and then I think moved to a 4S like over six years or something like that. Okay. Like I do look ahead. Being in technology, I look ahead, but if it's working, I don't replace it. It's weird. Microsoft or Google? Microsoft. Microsoft. How many emails do you get a day? Oh gosh, probably 150. 150. How many of those do you enjoy

reading? probably three. Which three? What are the three emails that you've been reading? Sales reports, tech reports. Yeah, positive reports. Positive reports, positive feedback. No, you have to communicate, right? So, like using, we use, we're a Microsoft shop, so we got Teams, and we have email, but you have to communicate. So I enjoy like communicating, but reading emails is not my favorite. What's the Microsoft platform that is, is there a Slack platform in Microsoft? Well, it's

Microsoft Teams. But Teams is allowed to use it? Teams has a chat. Yeah, so we chat and we have, we don't even have really phones. That's what we use for our primary means to talk and have meetings and remote meetings. But yeah, it's all good stuff and we're, We're definitely always looking, but right now we're just kind of, we're taking a little bit of a breather. We're kind of playing into more of the AI stuff and

that's really helping us out. But it is an amazing thing to think about five years ago where we were and where we are now. And again, I think it's been a great journey because we had nothing, right? And we're able to build it up from the ground. ChatGPT, Claude, Gemini, or Perplexity? I'm going to say Claude right now. Claude. Claude? Claude's winning. Now, we're setting up our own internal system as well. We'll probably use Copilot for

that because it's a Microsoft product. But with our data lake, which is built on Snowflake we've got all the I call them tributaries of all this data coming into it and We're getting ready within the next few months to be able to open that up to our internal team So they can actually hey, how did this shop do last Tuesday at nine o'clock compared to the rest of the system in a year ago, right? So people

can just go get their own data amazing Do you prefer phone calls or text messages? I like to talk to people. So phone calls, texts are okay, but you lose a lot, especially with my wife, I'd rather talk to her than a text because you lose a lot in the text. I'm also Eastern European, so yeah, I need to hear her voice to know how loud is she, how loud is she. Do you leave voicemails? Not

necessarily, no. No? No, I usually just hang up. Usually just hang up. Do you take photos or videos? Which do you prefer? Both. Both? Yeah. Okay. Google Maps or Apple Maps? Google Maps. And any app that we should know about that you use frequently that you enjoy that you don't think people should know about? Well, again, I told you about my music stuff. What music platform do you listen to? Museo is an app I use. It's

AI-generated songs and things like that. So I'll have a song idea, and I'll drop it in there, and then it just kind of creates. It's amazing to me that it can... create an entire production of a song. And I think there's another one, Suno, out there that, but yeah, in my personal time with the music stuff, I still play around with all that. And Shipley, you guys have an app? Shipley has a mobile app. We're actually

giving it a facelift with like our website, adding the AI components. And it'll also have voice AI on it. you'll be able to drive down the road and just go, hey, hey, Siri, I'd like to order Shipley. If you have the app, it'll pop open. If you got the payment already in there, you can tell it what you want. It'll confirm it and send it. That's awesome. If you guys, if you want to reach out to

me, I'm weirdly available at Sean P. Walchef. Instagram's always the fastest, but LinkedIn, TikTok. You can email me, Sean at Calibbq.media. We're always looking for the greatest information restaurateurs, storytellers, and technologists on Earth. So wherever they are, please let us know. Please go visit Shipley. I can't wait to go try some donuts. I don't know when I'm going to make it. But when I find a location and you guys are there, I will be there. Well,

yeah. Well, come to Texas. I'll take you over there. I'm coming. We're going. We'll be in Texas for the Food On Demand Conference. Awesome. So Dallas, Texas. Oh, yeah. There's plenty around there. Amazing. You got a deal. And please check out the Restaurant Franchise and Innovation Summit. I can't tell you the quality of restaurateurs and restaurant operators that are here at this show. I can't wait to come back. We really appreciate them allowing us to film

here. And thank you to Toast, our sponsors for this show, for believing in storytelling, believing in technology, giving us the opportunity to talk to people like Gary. Thank you guys for watching. As always, stay curious, get involved, but don't be afraid to ask for help. Thank you for watching. Thank you for listening. If you've made it this long, you are part of the community. You're part of the tribe. We can't do this alone. We started. No

one was listening. Now we have a community of digital hospitality leaders all over the globe. Please check out our new series called Restaurant Technology Substack. It's a Substack newsletter. It's free. It's some of our deep work on the best technology for restaurants. Also go to YouTube and subscribe to Kali BBQ Media. Kali BBQ Media on YouTube. We've been putting out a lot of new original content. Hopefully you guys like that content. If you want to work

with us, go to BeTheShow.media. We show up all over the United States, some international countries. We would love to work with you and your growing brand on digital storytelling. You can reach out to me anytime at Sean P. Welchef on Instagram. I'm weirdly available available. Stay curious, get involved. Don't be afraid to ask for help. We'll catch you next episode.

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