Kelly Esten, CMO of Toast, discusses how the company’s guest-first approach and innovative technology are transforming the restaurant industry by helping operators deliver outstanding experiences.

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Give An Ovation is the podcast where we interview restaurant owners, operators, and experts, to get their strategies and tactics so that youi can deliver a 5-star guest experience. Available on all major podcasting sites.

In today’s competitive restaurant landscape, having the right tools can make or break your guest experience. On this episode of Give an Ovation, Zack Oates talks to Kelly Esten, CMO of Toast, about the journey behind one of the industry’s leading POS systems and how it helps restaurateurs succeed by focusing on what truly matters: the guest experience. From automating marketing to building rugged hardware designed for the demanding restaurant environment, Kelly shares the strategies that keep Toast at the forefront of restaurant technology.

Here are some highlights:

[2:42] The Story Behind Toast’s Success

Kelly explains that Toast didn’t originally start as a POS company. The founders were driven by a simple problem—paying the bill faster at a bar—and pivoted to POS after realizing the operational challenges restaurants faced. She emphasizes that Toast’s success comes from staying true to its mission of helping restaurants thrive.

“Once you get into it, restaurants are a really diverse space, and that’s why focusing on their specific needs makes all the difference.” – Kelly Esten

[5:04] Balancing Guests, Operators, and Employees

Toast builds solutions that address the needs of operators, employees, and guests alike, which Kelly sees as essential for creating a superior guest experience. She discusses how empowering employees and using technology helps restaurants provide better hospitality and operate efficiently.

“The employee can’t deliver a great guest experience if they don’t have the tools they need.” – Kelly Esten

[8:14] Why Guest Relationships Matter More Than Ever

Kelly shares insights from research on how restaurateurs are increasingly focused on growing guest relationships, even in tough economic environments. She stresses that regular customers are crucial, and technology plays a key role in scaling those relationships.

“In these moments, your regulars matter the most.” – Kelly Esten

[12:28] Connecting with Guests Through Service Recovery

Zack highlights the importance of recovering unhappy guests, revealing that it can turn them into loyal fans. Kelly agrees and discusses how Toast equips restaurateurs with the tools to identify, recover, and re-engage with guests to drive long-term loyalty.

“How do you create true loyalty? It’s through connection.” – Zack Oates

[15:53] Tactics to Improve Guest Experience with Automation

Kelly shares how Toast is helping restaurants by simplifying marketing through automated campaigns, allowing operators to maintain guest engagement without getting bogged down in daily tasks.

“Our customers are often there because they love hospitality, not because they’re marketers. So, we focus on making things easy.” – Kelly Esten

[19:25] Who Deserves an Ovation?

Kelly gives a shoutout to Wisk Breakfast, a small restaurant near Dallas using AI-powered tools to streamline their marketing, creating emails in under 10 minutes and boosting their presence with minimal effort.

“They’re a great example of a smaller restaurant showing up in a bigger way because of technology.” – Kelly Esten

Learn More

To stay connected with Kelly and learn more about her work, follow her on LinkedIn . Interested in exploring how Toast can elevate your restaurant? Visit ToastTab.com to learn more.

Full Transcript

Speaker 1: 0:00

Welcome to another edition of Give an Ovation, the restaurant guest experience podcast, where I talk to industry experts to get their strategies and tactics you can use to create a five-star guest experience. This podcast is sponsored by Ovation, an operations and guest recovery platform for multi-unit restaurants that gives all the answers without annoying guests, with all the questions. Learn more at OvationUpcom. Join guests with all the questions. Learn more at OvationUpcom. And today we have a good friend of mine, someone that I am so excited for, someone that I even rocked out a different hat today For those who are watching, I got my Toast hat on because we have Kelly Esten. In seven short years she has worked her way up to the CMO of Toast and she is just a rock star. Way up to the CMO of Toast, and she is just a rock star. You meet her for two minutes and you will find out why she has such a meteoric career. Kelly, welcome to the podcast.

Speaker 2: 0:52

Zach, thank you so much for having me, and I can only say the same about you. You are such a force in the industry and love running into you whenever I do.

Speaker 1: 1:01

I know, and this is the first time that we have a recorded conversation. I do, I know, and this is this is the first time that we have a recorded conversation, which is, which is great, always fun to hang out with you, recorded or not. But tell me a little bit, kelly. I just for someone who is is looking at Toast. I mean at Toast, you look at you like such a huge company. What doesn’t the CMO do at Toast?

Speaker 2: 1:27

Oh, you know Toast is really all about what we can do to make restaurants successful, same goal as I know you have when you interact with your customers as well. And I think I have one of the most fun jobs at Toast because, from a marketing perspective, I get to talk all about. You know what we’re doing at Toast to make restaurants successful, interact with all kinds of customers all over the country and, increasingly, the world. I also get the opportunity to work with our partners. That’s a little bit under my purview as well, and so we love working with Ovation at Toast and over 200 other partners that really enhance the options that our restaurants have to find ways to make themselves successful, to find ways to differentiate through technology. And finally, I spend, as I think you know and many others, a little extra time with our enterprise customers as well, so making sure the largest brands on Toast are super successful and have all the support they need at the executive team to get what they need out of Toast.

Speaker 1: 2:21

Now, if you go back in time and someone were to sit down with me and would say, okay, zach, I got this idea for a point of sale company in the restaurant industry called Toast and when Toast first started I would have been like knowing what I know. Now I would have been like, hey look, really crowded space, really tough, probably not going to happen. Why has Toast been different?

Speaker 2: 2:42

Yeah, and actually, if you go back to the beginning of the Toast story, Toast actually didn’t start as a point-of-sale company at all. The founding story goes something like the three founders were sitting at a bar and wondering why it was taking so long to pay their bill and why technology and especially at the time mobile phones were becoming ubiquitous, the app store was really growing and they really saw the opportunity to pay the bill on the phone. And they joke that now, you know, more than 12 years later, we finally have that functionality at Toast. But what you know, it all started with, you know, wanting to solve this specific pain point for the guest experience and finding that when they went to go talk to restaurants about it, first of all, it was really hard to integrate with all of the different point-of-sale solutions out there. There were still servers in the back rooms of restaurants, Integrations weren’t as easy as they are today, and so they couldn’t find a path in. But what restaurateurs really wanted to talk about was some of the pain they had in their core operations, and so that’s why they pivoted to Point of Sale was actually to foundationally make all of the things we’re doing today, both at Toast and with our partners possible to really enhance that guest experience.

Speaker 2: 3:53

And they also got a lot of no’s on Point of Sale too, for all the reasons that you said. But what’s made us successful over the last 12 years is really our focus on restaurants and staying true to that mission, and we’ve been talking a lot lately about. You know, there’s a thousand little things that we do in the point of sale that you would never do if you didn’t focus on restaurants, Because you know, once you get into it, restaurants are a really diverse space and so understanding what a full service fine dining restaurant needs versus a quick counter service, there’s a lot of little things that makes the guest experience, the employee experience, operating the point of sale, the people in the kitchen, effective that you don’t get from just what seems like a simple point of sale that you throw on a counter to take orders. There’s a lot more to it.

Speaker 1: 4:39

Yeah, and especially looking at your focus on the roots and like it’s all about from the very start. It’s about how do we make it better for the guest right, the whole thing is focused on the guest, and I like that. I don’t know if you guys publicly say this, but to me it kind of seems like you put the guest first and the restaurant second, and by doing that it helps the restaurant the most, you know.

Speaker 2: 5:04

Yeah, yeah, it’s a great point. We think about three stakeholders whenever we build at Toast. We think about the operator, the guest and the employee, and all three of them are really important to the restaurant being successful. And when we think about enterprise brands as well, we extend that operator up to what we call the corporate teams, and so there’s different people that needs to interact with the technology across all of it, and the employee can’t deliver a great guest experience if they don’t have the tools they need. But many of our tools, and especially our partner’s tools, are guest-facing and so understanding that guest interaction and the surface that they’re seeing, how the employee is being empowered to deliver a great hospitality, to make great food, and then, finally, how the owner-operator or the corporate team has the right tools or not to do their jobs. Those are the three audiences that we build for at Toast and it really makes a difference to think of each of them because they have very different needs.

Speaker 1: 5:59

Totally. And is that, by the way, the founding story? Is that the reason that you guys are still ToastTabcom as opposed to you didn’t buy Toastcom away from some whatever big conglomerate I’m sure owns it, ToastTabcom?

Speaker 2: 6:14

was really that tablet and if you think about mobile as being one of the foundational elements that made Toast possible, I think about you know, when we go back to that founding story, some of those early decisions that made the difference for Toast mobile applications, mobile tablets, were really becoming ubiquitous and less expensive and the founders made the decision to go Android and that became super critical to Toast’s success, and one of the reasons why is because it’s given us control over the full stack, so we have the ability to design our own hardware and the hardware I’m sure you’ve seen me do this at trade shows like you can throw it on the ground, you can toss it in a blender, you can run it through the dishwasher and it still comes out working. Same thing, we own the operating system all the way up through the technology that we’re building the software on top.

Speaker 2: 7:06

And that ruggedness is so critical for a restaurant, because whatever you think can spill can spill and the heat and the water and everything’s happening, and so Toast Tab is really comes from this idea of that mobile tablet being pretty foundational to how we got started.

Speaker 1: 7:23

And look, I love me a good Mac product. But I’ll tell you what. Sometimes I feel like I sneeze too hard and my iPhone screen breaks.

Speaker 2: 7:32

You should see the back of my iPhone, because everyone talks about the screen breaking, but somehow I managed to break the back of it. I guess the way it fell when I dropped it, or whatever, you’re always doing things a little differently. Kelly, I love that about you, yeah yeah, and also running around like we all are, and my phone goes everywhere and so it definitely takes a beating.

Speaker 1: 8:04

Well, you know, and thinking about all of this as we come down to it, it’s like when you look at the guest, when you look at the employee, when you look at the, you know the operator, it really all funnels down to the guest right. Everything that we do in the restaurant industry is to create a great guest experience. What would you say is the most important aspect of guest experience nowadays?

Speaker 2: 8:14

Yeah, you know, we actually do. I think you probably know a lot of research into what restaurateurs are thinking and also what their guests are thinking. And for restaurateurs, what we’re really hearing from them is, even in this environment where profitability is front of mind, they’re focused on costs. They’re worried about what’s happening with inflation. When you actually ask them what’s top of mind and how they need help, it’s really about growing that guest relationship and making sure that they have a way to connect to that guest.

Speaker 2: 8:43

I actually heard a restaurateur who owns a couple restaurants here in the Boston area we were talking about. You know, what are the tactics that make a long-term restaurant successful in a tougher environment like this, where inflation is going high, and I thought she was going to go to the place of. You know, I’m really focused on my food costs or thinking about how I optimize labor, and she said in these moments is when your regulars matter the most and it’s so important to know my guest and to understand how I’m going to keep them coming into my restaurant on a regular basis, even when times are a little bit trickier.

Speaker 2: 9:18

And so I think to your point. You know the great restaurateurs know it’s really about the guest and that relationship. And how do you start to scale that relationship beyond? You know that one-to-one interaction. I recognize that person when they walk in the door. We all aspire to that, but hopefully there are many more guests that also we want to find a way to have technology help our teams recognize them when they walk in the door. And so it’s really about you know how do we help them own their guest data and understand what the guest’s thinking so they can create that one-to-one relationship?

Speaker 1: 9:51

I love that because I talk about this all the time on the podcast where it starts out with convenience, which is the expectations need to exceed the effort in order to try it out one or two times. And then, when you come in a few times, that’s because there’s consistency. I had this. I had a good experience the first time, the second time, the third time. Sure, I’ll come in four or five, six times, but then how do you create true loyalty? Like we’re talking, cater my wedding, there’s a big office party birthday event at your like. How do you create that? That’s not through convenience, that’s not just through consistency. It’s through connection, helping that person feel important and like that brand cares about them. Right.

Speaker 2: 10:35

Yeah, and to your point about, um, you know, figuring out how you come in the first time. It’s also, you know, the, just like you know we hear this about Toast. One of our most powerful channels in marketing at Toast is referrals. It’s one of our biggest channels, and that’s true for restaurants too. Right, they think about guests, hear from their friends oh, I love this place. I’m more likely to tell you, you know, to go to my favorite restaurant in Boston than to go to, you know, just one that’s a pretty good and on the list and pretty consistent. And so how do you become a favorite or how do you become loved? And that’s what’s really going to drive, you know, me telling my friends hey, these are the restaurants that you should try when you come into town. And it it is. We actually find that in our research data that guests are most influenced by recommendations from their friends, and those recommendations come from when people have that connection and they know that they’ll deliver on the expectation.

Speaker 1: 11:31

Because I don’t know what data. I don’t know if you guys have done this research I’m sure you have but we have found that the average retention rate of a guest is around 30%, and I don’t know. Is that about what you guys see at Toast as well?

Speaker 2: 11:47

You know I don’t have that data point off the top of my head from Toast. I’m sure someone does, but that sounds about right based on what I hear from our customers.

Speaker 1: 11:54

And in thinking about that, isn’t that just like so disappointing? I mean, think about that Like someone you spent coming from a marketing background. You spend all this money to get somebody in and only 30% of them are coming back Right and that’s a huge leaky bucket. But one of the things that we found is when you can create that connection and actually the best way, data wise, to create that connection is to recover an unhappy guest Right.

Speaker 1: 12:28

If there’s a negative experience in proper service recovery, that guest, according to our data, is worth 24 times that of the average guest in terms of their likelihood to leave review. They come back four times more often. They have a 68% likelihood to return. They spend more money at each visit Like they become a raving fan, which is just such an incredible opportunity, but it’s because of the connection like you’re talking about.

Speaker 2: 12:56

Yeah, it’s a great point and to your point about. You have all that amazing data on what it takes. You know what a recovery does for your business and what it takes to make a guest successful and what that looks like from a ROI perspective. But many restaurants don’t have the tools or the marketers for them, or how do the tools that we provide them, either at Toast or with our partners, give them the tools to understand that data, to capture that data and to know what to do when they get this data in their hands? It’s so much more powerful to know how to spend your time as a marketer.

Speaker 2: 13:40

I think about what it would be like to be a marketer for a restaurant and it’s like are you sending emails? Are you going on social? Are you doing podcasts? What is it that matters to your guests? And it’s a lot of what you’re talking about. As far as that individual reaching out, recovering someone, having them come back in how do we drive that repetitive behavior and that loyalty is a lot of what it comes down to from a marketing perspective, and it doesn’t sound like marketing, but it really is.

Speaker 1: 14:06

Absolutely, and the fact that one of the things I love about Toast, and one of the reasons that we’ve got so many customers who love Toast, is because Toast either does it or they partner, or you partner with people who can do it, and with these tight integrations it makes it feel much more like one platform, Whereas you go back to you know 2015, when you’re running a restaurant, either you have you’re on like a cash basis or you’ve got like 20 pieces of non-integrated technology and you’re you’re piecemealing all of this together and it just takes so much effort. It’s great to have a technology partner like Toast where it brings it all together.

Speaker 2: 14:47

Well, and one of the things that we’re helping restaurants do increasingly in spending some of our R&D resources on is really about, you have all these channels that guests interact with restaurants on now and how do you really help the restaurant see the guest across all of those channels? It’s one of the things that is one of the reasons to engage with tools like Ovation, but also our marketing tools and our partners’ marketing tools and loyalty programs is so that you can capture that guest data and you have someone to reach back out to when there’s an experience you need to recover, or even when you have exciting news to share, or just this week’s special that’s going to get someone to come back in, and so capturing that data and bringing it all together is a big focus for a platform like Toast. We want to be able to be the platform that allows restaurants to pull all those pieces together and add the components that are important to their business.

Speaker 1: 15:44

Amen, and now we’re starting to bleed a little bit into the tactics. So what are some tactics that you would recommend to restaurants to improve the guest experience?

Speaker 2: 15:53

Yeah, absolutely, you know.

Speaker 2: 15:54

As I was talking about before, you know, one of the things we’ve been really focused on is understanding that our typical customer at Toast who’s trying to run a marketing program isn’t a marketer, and so they often are there because they love hospitality, they love hosting and serving people, or they love food, or even they just saw a need in their own community for the restaurant that they built.

Speaker 2: 16:18

And so a lot of what we’ve been focused on recently and seeing people have success with is, you know, starting to build automated campaigns.

Speaker 2: 16:28

And one of the things that falls off the list when things get busy or things get, you know, tough in the restaurant is, you know, remembering to do things on an ongoing basis, those little drips or those little moments that keep you top of mind and keep people thinking about coming back.

Speaker 2: 16:44

So we’ve been putting together recommendation engines where we can just surface to you like, hey, you should think about sending an email to your regulars or targeting people who haven’t been here in 30 days, or running a happy birthday campaign, and can we make it so that all you have to do is say yes and we take care of the rest for you? Because what I think, what we’re seeing in our data is that it takes a lot of time to come up with these ideas, to implement them and then to get the ROI, and when we’re able to take a lot of the planning work off the table and just tell restaurateurs hey, here are five things that we think can work great for your specific customer base. It allows them to really get off and running and get back focused on the parts of their business they want to be focused on. So those are some of the things we spend time on that we’re seeing restaurants have a lot of success within their tools.

Speaker 1: 17:40

Yeah, because restauranteurs that I talk to, especially ones that when, as you’re, as you’re growing a brand, you may have one, two, three, four, 10 locations, it’s like you’re in it, you’re doing the thing that you love doing, which is usually around food and guests.

Speaker 2: 17:58

Right.

Speaker 1: 17:59

And it’s like. The other things are like I’m not a marketer, but you have to be a marketer in the restaurant industry. Like I’m not an expert on, you know operations, necessarily, but like, but you have to be an operations expert in the restaurant industry. And so that’s the challenge, is, you have to be good at every single thing. Right, you either got to hire it out, you got to learn it, or you got to partner with technology that’s going to help you do that. And I love that you’re investing in that.

Speaker 2: 18:28

Yeah, and to your point. It often is not the workflow where you’re sitting back at your computer drafting emails. It’s often that you’re on your feet, you’re out in the restaurant, you’re in the kitchen, you’re talking to guests, you’re on the phone, and so the way I see our restaurant customers spend their day is not behind the computer, you know, coming up with emails and pretty graphics. It’s really out in the restaurant doing the work, even to your point, at those 5, 10, 15 unit scales. And so how do we take some of that admin work off their plate and find ways to automate those things that they know they have to do to grow their business and even to keep the business successful, without kind of chaining them to a computer at a desk, like some of us spend our time doing?

Speaker 1: 19:13

Yeah, exactly Right. Well, where I know you? Obviously, kelly, you know a lot of people in this industry, but who is someone that deserves an ovation? Who is someone that we should be following?

Speaker 2: 19:25

One of our customers. They have a breakfast and lunch spot near Dallas and they also have an awesome Instagram account it’s at Wisk W-I-S-K breakfast and they recently started using our AI powered writing assistant, not only to automate their marketing, like we just talked about, but they’re actually testing out our AI writing assistant for us, and so AI is writing all of their emails for us, and the tool has cut their time to create an email from 30 minutes to less than 10. And so they’ve been really doing a lot more marketing with their email tools and seeing a lot of success in their business, and I think it’s a great example of a smaller restaurant concept showing up in a bigger way because of the technology that they’re deploying and able to see those results from their marketing campaigns.

Speaker 1: 20:10

Love that and and so check them out. Love, love that, and I gotta, I gotta try them out next time I’m in Dallas.

Speaker 2: 20:17

Yeah, We’ll be in Dallas soon. I’m sure this fall probably.

Speaker 1: 20:25

Oh, that’s right, we will be. Huh, I know there’s there’s like so many conferences going on, but it’s always fun to hang out, Kelly, I mean, obviously everybody knows you can find ToastTab on all the social medias, and so go go check out ToastTab. If you’re not on it, go go look into them. Where can people go if they want to learn more about you or hear more of your musings?

Speaker 2: 20:45

I’m on LinkedIn a lot, so you can find me, kelly Sennett Esten, on LinkedIn and, increasingly, as long as you’re happy with your toast content being mixed about 50-50 with the kids, you can find me on Instagram at Kelly Sennett.

Speaker 1: 20:59

Awesome. Well, kelly, for helping restaurants not get burnt by bad technology. Today’s ovation goes to you. Thank you for joining us on Give and Ovation.

Speaker 2: 21:08

Awesome. Thanks, Zach.

Speaker 1: 21:12

Thanks for joining us today. If you liked 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 OvationUpcom.

Thanks for reading! Make sure to check out the whole episode, as well as other interviews with restaurant gurus by checking out “Give an Ovation: A Podcast For Restaurants” on ovationup.com/podcast or your favorite place to listen to podcasts.

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