Sterling Douglass, Co-Founder and CEO of Chowly, joins Zack Oates to break down why AI is finally gaining real traction in the restaurant industry. After years of slow adoption across multiple tech waves, Sterling explains what has changed and why operators are now moving faster than ever.

Why AI Adoption Feels Different (02:30)

“Restaurants are running toward this.”

Sterling points out that unlike past technology shifts, operators are not resisting AI. Instead, they are actively seeking it out, learning it, and experimenting with it in real time.

The COVID Effect on Tech Adoption (03:10)

“Technology was the savior.”

COVID forced restaurants to adopt digital tools just to survive. That experience built a foundation of comfort with technology, making AI feel like a natural next step rather than a risky leap.

From Chatbot to Operator Tool (15:00)

“Stop thinking of it as a better version of Google.”

Sterling emphasizes a mindset shift. AI is not just for answering questions. It is a tool that can execute tasks, automate workflows, and remove operational friction.

Turning Feedback Into Action (11:00)

“We remediated 32 issues without the customer ever knowing.”

By using guest feedback data, Sterling’s team identifies problems like incorrect hours or technical issues and resolves them before they escalate. This turns feedback into a proactive system rather than a reactive one.

The First AI Breakthrough Moment (16:00)

“Once you see it perform a task, it just opens your world.”

Sterling explains that adoption accelerates when operators experience a small but meaningful win. That first success changes how they think about their time, their team, and what is possible.

This conversation highlights a shift happening across the industry. AI is no longer theoretical or optional. Operators who start small, stay curious, and focus on real use cases will move faster and build a meaningful advantage.

Links:

https://www.linkedin.com/in/sterlingddouglass/

https://www.linkedin.com/company/chowlyinc/about/

https://chowly.com/

Transcript

00:00:00:09 – 00:00:24:16

Zack Oates

Welcome to another edition of Give an Ovation, The Restaurant Guest Experience podcast. I’m your host, Zack Oates, and each week I chat with industry experts to uncover their strategies and tactics to help you create a five star guest experience. This podcast is powered by ovation, the feedback and operations platform built for multi-node restaurants. Learn what’s actually happening in your restaurants and exactly how to improve while driving revenue.

00:00:24:19 – 00:00:44:19

Zack Oates

Learn more at ovation up.com. And today we have got an icon of the industry Sterling Douglass, the co-founder and CEO of Charlie Sterling. You have been a pillar for a full decade now. How does that feel to have done something in your life for ten years?

00:00:44:20 – 00:01:02:11

Sterling Douglass

Yeah, I don’t I don’t know if it’s a good thing. I don’t know. I would say it’s something I brag about. Sometimes I think about ten years and I go, Holy like cow. I mean, I’ve been in here a while and also I was a baby when we started. But no, man, it’s honestly the most fun part is getting to see all the different waves the restaurant industry has kind of faced.

00:01:02:13 – 00:01:08:12

Sterling Douglass

Right. I got to see the third parties, the cloud POS, the online ordering, and now the I where the ghost kitchens.

00:01:08:12 – 00:01:09:06

Zack Oates

You remember those?

00:01:09:12 – 00:01:16:24

Sterling Douglass

Those were. Yeah. We still to this day have over a thousand virtual concepts on our platforms and that’s amazing.

00:01:17:04 – 00:01:49:04

Zack Oates

Well, and what’s interesting is that as you see these different changes, there is such a wide variety of adapting and fearing tech. And one of the things that’s really interesting about this wave that we see with AI is I’m seeing restaurants lean into this more than ever. Yeah, and it’s incredible to see how quickly they’re adapting this. And I know that you talk a lot about AI and you are a huge proponent of AI.

00:01:49:08 – 00:01:54:15

Zack Oates

And so, you know, talk to us about your podcast and your theory on AI.

00:01:54:17 – 00:02:12:19

Sterling Douglass

To your point, on the AI embracing tech, right? The restaurant industry always gets a terrible a terrible rap. Like they don’t embrace tact. They’re always the slowest to adopt and all these things and to an extent that’s true. I think back to when we first started, Charlie, I was literally walking around Wrigleyville in Chicago, just walking into restaurants and trying to get them on the platform.

00:02:12:21 – 00:02:33:06

Sterling Douglass

And one of the biggest issues that we had, one of the biggest objections we had is they just didn’t believe we could do it. Like, I just literally were just like, you can’t do that. Like, you know, some guy tried to do this or something and that to me was like a perfect example of how they weren’t adopting technology and how they weren’t embracing it, how skeptical they were, and how they didn’t believe any of it.

00:02:33:08 – 00:02:56:22

Sterling Douglass

And on the AI side, I see almost none of that. Like restaurants are running toward this for a lot of different reasons. But for me, it’s exciting because after watching a space get hit by wave after wave after wave, now I’m actually seeing them like, just embrace this and all in wanting to learn more. Going to boot camps, doing certifications like pushing the envelope, all the things that they should have been doing for all these different waves.

00:02:56:24 – 00:03:01:10

Sterling Douglass

And now I think that we’re not going to see such a slow adoption on the restaurant side.

00:03:01:12 – 00:03:05:23

Zack Oates

Why is that? What’s different about this than prior waves?

00:03:06:00 – 00:03:08:08

Sterling Douglass

Yeah, I think there’s a few drivers here. I mean.

00:03:08:08 – 00:03:08:22

Zack Oates

One.

00:03:08:22 – 00:03:27:18

Sterling Douglass

Is you just said Covid really changed the mindset of the restaurant tour during Covid. Technology was the savior. Was the only way you could keep your doors open while there was online ordering. There are all these different things. And so every restaurant kind of had to learn this whole digital experience. And so that really got them much more comfortable with tech and more tech enabled.

00:03:27:20 – 00:03:45:23

Sterling Douglass

They kind of exploded. We did a workshop a couple of years ago with, like 200 different independent operators, and we asked them how many tech solutions they had, and the average is 28. The average restaurant had 28 pieces of software to run the restaurant. Now, I think that’s come down a lot as we’ve seen more consolidation. But I think that you kind of saw that big push.

00:03:45:23 – 00:04:03:02

Sterling Douglass

And so now on the AI side, I think that’s a big driver. The other big driver is the AI brings efficiency. AI helps like make people more efficient. People can get more done. It’s great for learning. A half of the sessions that I do. AI is teaching me something and doing a research for me. These are things that entrepreneurs love, right?

00:04:03:02 – 00:04:17:00

Sterling Douglass

And they’re drawn to. And so I think there’s just kind of like this learning nature, this efficiency. And then you’ve also got this. You know, wave of I know tech, I know working on my restaurant. I’ve seen it before. And I think those three things really combined into a lot faster adoption.

00:04:17:02 – 00:04:20:08

Zack Oates

Are these the things that you discuss on your podcast?

00:04:20:10 – 00:04:33:03

Sterling Douglass

Yeah, we talk a lot about adoption. So real quick we do a podcast AI for restaurants easily found on LinkedIn. It’s on YouTube, its latest AI for restaurants, Sky. So we say I just for the SEO but.

00:04:33:05 – 00:04:35:02

Zack Oates

Or the Geo.

00:04:35:04 – 00:04:49:16

Sterling Douglass

Yes. Right. We do talk a lot about Geo. Me and Aaron Newton from. Thanks. He’s the co-founder, chief data officer. Him and I have been trading notes on AI for about a year and a half. And we talk about a lot of things. We talk about restaurants, adoption. We talk about why they’re adopting it. We talk about how they can adopt it.

00:04:49:21 – 00:05:05:13

Sterling Douglass

We talk about use case from big restaurants using AI, little restaurants using AI. And one of the more interesting topics we talk about is how we get our companies to adopt AI, because at the end of the day, like that’s still a struggle. Thinks it’s done a really good job getting their team in it. We’d have like a very different approach on the Charlie side.

00:05:05:13 – 00:05:08:02

Sterling Douglass

And so we go over a lot of those different things on the episodes.

00:05:08:04 – 00:05:28:21

Zack Oates

And it really is interesting because everyone thinks like, oh, you’re a tech company, which means everyone at your company knows how to use AI, and they’re all using cloud code to code stuff up. But there’s still a lot of training because as we look at ovation, for example, we have a really long tenure of people. People like standing at ovation as a result.

00:05:28:23 – 00:05:48:23

Zack Oates

And by the way, everyone’s really, really busy at ovation, right? And so there’s not like we don’t just have two days a week that people can dedicate to learning about AI. And so we have the same struggles that a lot of restaurants have, which is you’re so busy working on stuff that it’s hard to really, like, think about stuff.

00:05:48:23 – 00:05:55:12

Zack Oates

And so what do you do to help your team really set aside and dedicate time to learn about AI?

00:05:55:14 – 00:06:15:14

Sterling Douglass

Every interaction is an opportunity to use. You know, Aaron, you know, I him and I talk about like, what does it mean for your company to be like after. So like, how do you know like you’re either far enough along you’ve reached a whatever milestone. So his theory is that if until every single person starts every single task with cloud code, you’re not, you know, an AI first company.

00:06:15:16 – 00:06:33:23

Sterling Douglass

And so every interaction that you have can help get you there. Whether you’re looking at a marketing website, whether you’re looking at a customer situation, whether you’re trying to build like your knowledge base, it’s really trying to make sure that you’re are constantly reinforcing the examples and when you can use it and then actually doing it with them.

00:06:33:24 – 00:06:48:15

Sterling Douglass

Tons of pairing. I pair with everybody at our company to get them in there. We do screen shares where you literally just watch. If someone’s new to it. I’ll screen share just so they can watch me prompt just so they can see how I’m phrasing. And then they can ask questions when they see tool calls in the back.

00:06:48:21 – 00:07:04:16

Sterling Douglass

Or how do you get it to talk to Salesforce? Like how do you do that? Like I want to do that and then you you go over kind of you get them authorize and get the MCP set up. And so it’s more just like taking every single opportunity you can to push the ball forward. Some people do hackathon, some people do training days, some people do dedicated days for it.

00:07:04:16 – 00:07:18:23

Sterling Douglass

I think there’s a lot of different ways to get to that place. And every company, whether it’s a restaurant, the tech company, an Hvac company or whatever, are all trying to figure out how their businesses kind of go on that journey. And we talk a lot about that on the show.

00:07:19:00 – 00:07:42:03

Zack Oates

I think that’s so powerful, that code pairing, because one of the things that as I was learning AI and I mean, we’re all constantly learning AI, but literally sitting down with people and just having them open up your laptop and like, share your screen and just show me what you’re doing. That’s how I was able to learn, because at some point, you need to take AI from this.

00:07:42:05 – 00:08:08:22

Zack Oates

Oh, this is like a really cool Google. That’s wrong 30% of the time to like, what would you do if you had ten people working for you? So how would your mind look at a task differently if you had ten people that were there behind you? And and the reason I say ten as opposed to like 100 or 1000, which is what it really is, is because it at least gets you thinking, what things do I not need to do?

00:08:08:22 – 00:08:22:21

Zack Oates

What things is it possible to have? I do now? Where have you run into some issues with AI? Where have you found like hey, this is hard to here’s a task that I just might not make sense for.

00:08:22:23 – 00:08:43:04

Sterling Douglass

So it’s funny, I used to have those thoughts and then I realized that someone every single time has figured it out. So I kind of compare this like, you know, like the bigger boat analogy. Like, there’s always a bigger boat. Yeah, yeah. No matter how big. Like I don’t have a boat, but no matter how big your boat is, there’s always someone with a bigger boat in this harbor or the next harbor.

00:08:43:05 – 00:09:01:00

Sterling Douglass

Like there’s always there’s only one person with the biggest boat. And in AI, it’s like the same. There’s there’s someone is using it differently and better than, you know, no matter how well you’re using it. Aaron and I literally just talked about we have like 15 autonomous go to market agents, Charlie. And he was like, that is so cool.

00:09:01:05 – 00:09:29:13

Sterling Douglass

But then he has this amazing reporting application that gathers all the different reports, everybody’s have their run, makes data models more efficient and surfaces it to people and then also services it to customers is amazing thing called Sherlock and I’m sitting there like that is so cool. I tried I couldn’t do that. Like I ran into this issue and that issue and he was able to figure out, but at the same time he was like, well, I don’t know how you get these autonomous agents to actually do the work I and do it well and consistently and how you do the checks.

00:09:29:17 – 00:09:57:21

Sterling Douglass

And so you could talk to anybody and you’ll find them doing a use case where they’re doing it better than you. They figured out something. So I’ve really yet to come into it. I mean, obviously like AI isn’t washing dishes. It’s not plating. It’s not it’s not doing those things. But from a tactical perspective, I think it’s just a matter of imagination, bandwidth, and just an infinite amount of curiosity for it to accomplish, you know, the amazing things that it can do.

00:09:57:23 – 00:10:15:05

Zack Oates

And one of the things I find to be really interesting is you’re one of the only partners I know of that’s really using ovation data. Yeah. To help your business. So it’s not even and that comes down to like the curiosity and the creativity the that you’re talking about.

00:10:15:07 – 00:10:39:00

Sterling Douglass

Yeah. So for those who don’t know, we we have a good partnership with ovation where they are basically like embedded into our product and into our online ordering product, so that even like we predominantly work with independent operators, 1 to 10 locations. And so we can actually directly integrate all those surveys, have them go out, have all the responses show up in our platform so that you kind of have this one place to work with, with everybody, which has been an awesome partnership.

00:10:39:00 – 00:11:01:12

Sterling Douglass

Thank you Zach, thank you. Really. And the team, it’s been really cool to see that come together. But one of the things that we realized we could do a few months ago is that the survey data that these diners are filling out, it’s not always about the food or about the staff or about the cleanliness. Sometimes it’s about the application, sometimes it’s about the website, sometimes it’s about the restaurant was actually closed.

00:11:01:12 – 00:11:22:20

Sterling Douglass

But in order went through which would cite this could be a technology issue. And so we ended up having it do is every day we look at all of our review responses across, you know, got a few over a thousand restaurants with this now. And we comb through and filter them and look for ones that could be either, configuration issue or maybe there’s a bug and then it goes through, creates us.

00:11:22:20 – 00:11:39:13

Sterling Douglass

Then it creates a, support case for them automatically, and then it even tries to then help the support case and say, hey, I looked into this configuration and saw this is an issue. Either we fix it or we can tell the restaurant to fix that. Or this might be a bug. And now the product team can kind of take it over and then go refine it.

00:11:39:15 – 00:11:52:15

Sterling Douglass

And so it’s one of these cases where we’ve actually been able to use the available data that we have to make our product better, which has been a really cool use case and something I imagine your customers, if they’re not already doing, will be asking you to do so.

00:11:52:17 – 00:12:13:06

Zack Oates

Yeah, because I mean, we analyze and we show them, hey, if there’s ever a tech issue or an ordering issue, we surface those to them. And that’s been awesome because we’ve seen people where they have, not with Charlie, but there is an issue with one of our partners where they were not putting modifiers onto the online orders.

00:12:13:12 – 00:12:16:00

Zack Oates

And so and this was a sandwich company.

00:12:16:01 – 00:12:17:16

Sterling Douglass

So just getting two pieces of bread.

00:12:17:20 – 00:12:36:14

Zack Oates

Yeah. Well, well they were like ordering the sandwich and then saying like oh but I don’t want sauce on it. Right. Well they don’t want sauce. Wasn’t showing up. And so they were getting a lot of complaints about their food for online orders. But they realized that it was a tech issue. And so they were able to go in there, talk to their vendor, get that fixed.

00:12:36:16 – 00:12:52:11

Zack Oates

But it’s amazing that they’ll flip that script. And if you’re using Charlie now, Charlie’s just automatically going in there seeing, oh, there might be a tech issue. We’re looking into it and we patch the fix before it even becomes a serious issue.

00:12:52:13 – 00:13:04:15

Sterling Douglass

In the month of March, we remediated 32 issues for our customers without the customer ever knowing what the issue existed because their diners basically told us.

00:13:04:17 – 00:13:26:06

Zack Oates

And that’s at the end of the day, there’s two things that every restaurant is trying to do increase profits and improve the guest experience. Right. And when you’re able to fix these issues before you see a trend with them, before it becomes like, hey, 30 people have had this issue. But now with Charlie, it’s like one person had the issue and it got fixed.

00:13:26:06 – 00:13:41:02

Zack Oates

It’s like, that is the power of AI because you can’t hire 50 people to go and read every single piece of review, pull out that feedback, create those tickets. And like historically, that was the cost of that going to service.

00:13:41:04 – 00:13:59:21

Sterling Douglass

And what it ends up being almost like of the 32 issues, only affects 30 of them, where someone went into basically like toast, point of sale, another point of sale, and then changed the hours and didn’t reflect those and other places. So we can go fix that for you, which is what we ended up doing more getting, making sure that we had the right hours.

00:13:59:23 – 00:14:19:13

Sterling Douglass

And so it’s really cool because you can’t especially like some of these point of sale systems. There’s four different places you can put in hours. You have menu hours, your vacations, hours. You end up with all these permutations. So trying to do this programmatically is really difficult, right. Because we have 60 different point of sale integration. So you multiply this out and all of a sudden you have it’s like a Coke freestyle machine.

00:14:19:13 – 00:14:35:20

Sterling Douglass

There’s 1.2 million different combinations for you to check. And you can do. And so by, you know, this is a nice one of those very boring use cases where AI helps make the product better, the experience better, and ultimately benefits the customer, which in my mind is always the end goal with these types of things.

00:14:35:22 – 00:14:50:11

Zack Oates

So restaurant owner operator listening right now, what advice do you have for them about their like Sterling I feel so far behind an I like, where do I get started? Besides listening to your podcast, I restaurant that I.

00:14:50:13 – 00:15:18:22

Sterling Douglass

Right now everybody feels behind and everybody is behind. No one is ahead in the second you think you’re ahead, I will go find someone, who will make you feel better about. There’s always a burger about and for getting started. Like the chat interfaces are great, but the big hump to get over is to stop thinking of them as a chat bot or a better version of googling something, and start thinking of them as tools that can do tasks.

00:15:18:24 – 00:15:39:08

Sterling Douglass

And the best way to do that is to try to find the simplest task that you understand and have it do it. And that task could just be scraping something from the internet once a week and sending you a message. It could be grabbing the weather for the day and just putting that data somewhere. You don’t have to vibe code.

00:15:39:08 – 00:15:59:21

Sterling Douglass

Humongous applications have to try to build these giant MSPs or scales. There’s a lot of things out of the box, but just once you start to see it and this has happened to every single person, including myself, once you see it perform a task, it just opens your world. You have that like you have that oh shit moment where you’re like, oh my God, I could also do this in this and this.

00:15:59:21 – 00:16:26:13

Sterling Douglass

It’s better than how we were doing it before. This is going to make I’m going to save time. I’m gonna have a better experience. Customers are going to be happier. We’re going to be more profitable. The brain starts spinning. Every person that I’ve worked with has ends up having that moment. For me, it was opening a Jira ticket like I know that sounds like crazy, but like I literally was able to just describe an issue in normal natural language and I was able to perfectly format it, do research, and then open up a JIRA ticket that I acceptance criteria.

00:16:26:19 – 00:16:40:08

Sterling Douglass

And it was a better ticket than our humans could do and in any short amount of time. That was that moment for me. But I just think anyone can have that moment. So trying to figure out what that task is and then getting it done, that’s how you get over the hump. But I think that’s how you get the most use out of it.

00:16:40:08 – 00:16:43:20

Sterling Douglass

And any restaurant operator owner can do that today, I love that.

00:16:43:20 – 00:17:08:02

Zack Oates

I think that’s exactly the point. It’s like you don’t need to like if you want to go run a marathon, you don’t need to go buy shoes and an outfit. Just like put on what you have, put on some shoes and go jog around the block and then you’re like, oh, okay, I could jog. Then like you start to get into it and there’s a lot of levels of what that means, but just start jogging.

00:17:08:04 – 00:17:26:04

Zack Oates

And I think that I love that you start with the smallest task you could think of. And if you’re not sure what that is, go on and have it scrape your Google reviews once a week and just send you an update of. Here’s what people have said about you this last week, and have it send you a slack message.

00:17:26:04 – 00:17:39:00

Zack Oates

Like, that is a great first project to just get your feet wet anyway, but there’s lots of them. And if you don’t know what to do, get on to Claude and say, hey, I’m trying to do my first project. Here’s my role, here’s what I do.

00:17:39:00 – 00:17:48:13

Sterling Douglass

What should it interview you? Yeah, I got the interview all the time, asked me ten questions and about what I do. And then you make a suggestion about what we can build together. It’s a great strategy.

00:17:48:15 – 00:17:53:03

Zack Oates

Sterling, who deserves an ovation, who is someone that we should be following?

00:17:53:05 – 00:18:27:22

Sterling Douglass

Oh, man, there are some. There are so many people as base. I mean, I think any restaurant independent operator or any restaurant’s IT team or marketing person that has gone to a boot camp that has gone and gotten a certification that spent four hours watching YouTube videos and building a little application and showing their team. Anybody who has taken the Red Bell accepted that I is going to make them better, and they don’t necessarily know how, but they’re just going to go do it.

00:18:27:24 – 00:18:40:15

Sterling Douglass

Every single one of them deserves innovation because they’re the ones that are going to help push this industry forward and help get rid of that moniker that restaurants are slow to adopt because they’re not going to be this time because of those people.

00:18:40:17 – 00:18:44:23

Zack Oates

Amen. Sterling, how do people find and follow you?

00:18:45:00 – 00:19:01:12

Sterling Douglass

Very active on LinkedIn. That’s basically the only social media I’m active on. So do lots of paths, share lots of things in the pod, things that we’re learning. Telecoms want to learn more about Charlie. And we’ve got tons of things on our platform and lots AI in there as well. But those are usually the best places to get all of us and the learn more.

00:19:01:16 – 00:19:03:02

Zack Oates

And the podcast again.

00:19:03:04 – 00:19:04:23

Sterling Douglass

I for restaurants I.

00:19:05:04 – 00:19:15:20

Zack Oates

There you go. Well Sterling for helping us remember that the AI in AI does require a lot less intelligence than it used to. Today’s ovation goes to you. Thank you for joining us on Giving Ovation.

00:19:15:22 – 00:19:17:02

Sterling Douglass

Thanks, Zach.

00:19:17:04 – 00:19:39:15

Zack Oates

Thanks for joining us today. If you like this episode, leave us a review on Apple Podcasts or your favorite place to listen. We’re all about feedback here. Again, this episode was sponsored by ovation, a two question, SMS based, actionable guest feedback platform built for multi-unit restaurants. If you’d like to learn how we can help you measure and create a better guest experience, visit us at ovation up.com.