On today’s episode of the Me, Myself, and AI podcast, Wendy’s product manager Will Croushorn joins host Sam Ransbotham to share how FreshAi, the fast-food restaurant’s voice-based AI ordering system, is reinventing the drive-through experience for millions of customers. From handling 200 billion ways to order a Dave’s Double burger to making fast food more accessible for guests in multiple languages, Will reveals how empathy and innovation will positively impact the future of convenience. Learn how his team turns speech data into insight, builds trust in automation, and can even hide a few Easter eggs in your next order.
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Transcript
Allison Ryder: How can AI remove barriers and make more seamless, enjoyable customer experiences possible? Find out on today’s episode.
Will Croushorn: I’m Will Croushorn from Wendy’s, and you’re listening to Me, Myself, and AI.
Sam Ransbotham: Welcome to Me, Myself, and AI, a podcast from MIT Sloan Management Review exploring the future of artificial intelligence. I’m Sam Ransbotham, professor of analytics at Boston College. I’ve been researching data, analytics, and AI at MIT SMR since 2014, with research articles, annual industry reports, case studies, and now 12 seasons of podcast episodes. In each episode, corporate leaders, cutting-edge researchers, and AI policy makers join us to break down what separates AI hype from AI success.
Hi, listeners. Thanks everyone for joining us again. Our guest today is Will Croushorn, product manager at Wendy’s. Most of you are familiar with Wendy’s; it’s an international fast-food restaurant. Will has a fascinating background, which I’m hoping we have time to get into. At Wendy’s, he’s been involved with the FreshAi initiative, which is using AI agents to take drive-through orders. Will, [it’s] great to have you on the podcast.
Will Croushorn: Thank you, Sam. I’m really excited to be here.
Sam Ransbotham: How did you get interested in artificial intelligence?
Will Croushorn: I was working for a company in Nashville. I’m by nature a pretty curious human. I remember the first time that I typed into ChatGPT. It was a really simple prompt, and it was like magic. I put in a sentence. I think it came back with like two sentences or something. This was back in early 2023. And I remember thinking, “Wow, this is incredible.” I’d never experienced anything like this.
What also stood out to me was there are very few moments in human history that are this democratized. I was sitting around a table with the CEO and engineers and all our data scientists, and I was a product person, and we were all figuring out [ChatGPT] together. Literally every week we’d show up and be like, “Oh, I learned this,” or “Oh, I tried this.” And there [are] very few moments like that where nobody knows what to do with this technology, and I had the thought of, “I want to help lead that.”
So fast-forward, [and I] ended up getting in contact with the team at Wendy’s. [I] was absolutely fascinated by the work, [which] is still very, very early with FreshAi. The thing that has driven me to this day is, yes, we can automate things, but the thing that’s really fascinating to me, and that’s helped drive the work that we’ve done with FreshAi, is how do you do something different? How do you use this technology to serve customers in ways that just weren’t possible before? For us, that looks like creating accessibility. It looks like creating experiences. But it all sums back to, “Wow, I’ve never experienced anything like this before. What are the cool ways that we can use that?”
Sam Ransbotham: That’s a great point, because there’ve been no human species before that have ever had this experience, so we’re all having to learn it together. And I like your perspective [that] it brought everybody down to level ground. I think about that with the students … I talk to in class. They’re thinking about what they’re going to do in the job market, and I like to remind them that nobody has more than three or four years’ experience in this, max.
So you mentioned FreshAi. Tell us about FreshAi, how it works, and I think that’ll lead to some of the discussions about accessibility and things that you alluded to.
Will Croushorn: So we started out with this question of, “Can you take an order in the drive-through?” Right now, 2025, moving to 2026, that sounds fairly simple, but at the time that was pretty groundbreaking. “Can you handle this?” The drive-through is a really complex place.
There’s something like 200 billion ways to order a Dave’s Double. That’s just in English. If you tried to order our [entire] menu, it’s something like 67 trillion different ways to order in English. Everybody has this feeling of, “Oh, I just have a normal order.” If I’ve learned anything in this process, there is no such thing as a normal order.
Customers will pull up and they’ll say, “Remove that green thing,” or, “Oh, wait, that last thing, I don’t want that.” We say one thing, but we intend something entirely different than the words that we use. So it’s really a giant, complex math problem with a lot of emotions tied up.
Drive-throughs are complex places. Mom pulls into the drive-through. Kids are screaming in the back. There’s a line full of cars. She’s tired from a long day at work, and she just wants her food, and she wants it fast. There’s just all of this pressure and stress. [She’s] trying to [be] budget friendly. And then somebody comes over the speaker box, [saying] “Hello, can I help you?” Sometimes friendly, sometimes not.
And so we set out [to find out] can we take orders? And [we] quickly realized there’s so much more opportunity to use AI. With FreshAi, a customer can pull up, they can order in either English or in Spanish, currently. We’re working on expanding to other languages. The agent completely handles the order. It’ll say, “Welcome to Wendy’s. What can I get you?” And you can throw almost anything at it. The agent’s going to be able to handle it. And then onscreen, you’re going to see on a digital menu board, you’re going to see your order.
We’ve done a lot of research to understand, looking at the cognitive load, how do we help guests order in an easier process? One of the ways that we do that is we actually will show you the transcript so you can see what the agent is saying, [and] you can see what you are saying. And it does a couple of things: It gives you a little bit of trust to know, “Oh, it heard me correctly.” Then also for customers or guests [who] might have hearing challenges, it also gives that reassurance of, “I know it’s happening on the screen.”
Sam Ransbotham: I liked your point there that we all think our order is normal, but everybody’s normal. It reminds me of a study back in the ’50s in the Air Force where they measured the average pilot, and the average pilot had arms of this length and a height of this length, etc. They found the average. And it turns out that there [were] exactly zero pilots [who] were average. Everybody was average, but there was no one [who] was exactly that average specification. So, yeah, I think my order is normal, but I guess everyone else thinks that their order is normal, too.
Will Croushorn: It’s amazing to see. We’ve started to see all of these regional trends. There are mustard parts of the country. There are ketchup-dominant parts of the country.
Sam Ransbotham: How accurate are these systems at getting these orders right? I’m not even thinking that the humans are accurate a hundred percent of the time either, though. That’s not a good benchmark.
Will Croushorn: They definitely are not. Right now, we are handling about 95% of the orders that come through. It’s about 150,000 orders every day, and we’re continuing to add sites. What we see [is] it is extremely accurate, and it [has] consistency.
I feel really strongly if we want to build the right thing, we have to understand the customers [who] are going through the drive-through and understand what are their needs, what are their preferences.
Sam Ransbotham: I like the idea of the confirmation, too. You’re talking about the screen. One of the things that’s always a mystery: Historically you order something and you come around, it’s not what you wanted. You at least can get that confirmation that what has happened has happened. Talk about how the accessibility part of that works.
Will Croushorn: So we’ve done quite a bit of work around this. What drives me with FreshAi is a customer should be able to pull up and order in a drive-through in any language, with any need, and it just works. It should be an afterthought.
I spent a little bit of time in the Middle East, and when I was learning Kurdish, I walked into the dukan, the market, and I just needed one cucumber. I walked out of that store with two bags. I have a master’s degree, and I couldn’t communicate, “I want one cucumber.” It was humiliating. There [are] deep emotions with that, and it stuck with me. One of the things as we’ve been building out this platform is nobody should feel that. If you pull up and you don’t speak fluent English, that shouldn’t be a barrier.
How do we widen the road? We’ve done that in a couple of ways. We’ve built FreshAi in tandem with Google Cloud. And we’ve worked really closely with them to train out our Spanish model. What’s really cool with that is before, say, in rural Ohio, we may or may not have [a] crew that speaks fluent Spanish. And so that customer, they can choose to order on the app, or maybe they pull up and they only know the word for hamburger, and so they might get an order, but it might not be the order that they want. With FreshAi, a customer can pull up — I actually saw this in Miami recently; it’s a location that is Spanish dominant, and a customer pulled up and was able to order in English, so [it was] the flip of most of what we’ve been training them.
What we see is customers are spending more. There’s more delight, and it’s just easier. You’ve removed that barrier. So that’s one of the ways we’re continuing to expand that. The other area that I’m incredibly excited about: We’ve recently brought in a speech therapist, and one of the pieces of feedback was the agent is interrupting. It’s a speech-to-text model. Language is incredibly hard to guess. Where do you jump in? Where do you hold back? So those are some of the things that we’re still [working on].
One of the pieces of feedback was the agent is interrupting too much and, because of that, feels rude. So what we did was we said, “All right, well, what’s the edge case? What’s the most extreme that we probably should account for?” Well, one of those is atypical speech. We have something like 10% of the U.S. population has some sort of stutter, and so we said, “All right, well, can the agent handle that?” So we brought in a specialist and literally just spent a day driving through our drive-through [and] driving through competitor drive-throughs.
I’ll tell you one of the things that we saw at a competitor drive-through as we pulled up. His name’s Travis. Travis went to order, and there’s a privacy screen. And in order to get past it, you have to say, “OK, I’m ready.” But you have to do it within a certain time frame. Well, because of his stutter, he wasn’t able to do it. And so he was literally barricaded from being able to order, which was a terrible experience. It was also just really bad for business.
Travis is like, “I would never go back to this place because that was so bad.” So thankfully, we pulled up to a FreshAi location, and it handled his order perfectly, but we spent literally two hours, [with] him just going through the drive-through trying to test this as hard as we could.
What’s amazing is we learned so much from it. We have pages and pages of feedback. And we go and roll out those updates, and those updates are now helping somewhere around 10,000 people a day. That’s the power of this technology — to help the business but also to do really good. And we’re not even scratching the surface yet.
Sam Ransbotham: One of the fun things that’s come out of a lot of episodes, and [I’m thinking] back to one of our early episodes on DHL, [is] the first day is the worst day of AI. What you’ve done is provided an excellent example of that, as these systems, if you can get a minimum in place, they can start to get better all the time. You say English and Spanish now, but there’s nothing conceptually that prevents you from going further than that. And, as you said, that gets rolled out in the software update. That feels pretty huge.
One thing that came out very strong is the idea that you can meet people where they are, and the idea that we could, for example, train a lot of workers to recognize different languages, recognize different regional differences, even my beautiful Southern accent and, you know, Will has a beautiful Southern accent, too. We could do that, but it’s really hard to do it at scale. So what this is pointing to is the ability to use this technology to reach people where they are. And your examples of the impairment give a lot of hope that we can go a lot further with that, beyond the drive-through.
Will Croushorn: One of the things that fascinates me. … I think the drive-through is just a starting point, but I see this technology … [allowing] us to do things that, again, you could never do this before at scale and [with] consistency so that you can guarantee, “Hey, if I go to this location in Miami, it’s going to be personalized to me, but it’s going to be the same experience and consistent quality as, say, [if] I go to the U.K. or Italy. It doesn’t matter where I am; it’s a consistent brand experience every time.”
The way that we’ve tried to approach this is, “What are the things that AI can do really, really well?” and let it do that. And then, “What are the things that a human does really well?” and empower them to do that exceptionally well.
So there’s this ability to free up the human labor to really focus on the things that are really human and to have this consistent experience that was not possible before.
Sam Ransbotham: All this seems wonderful. What are the problems? What are the difficulties? And is it all just technical difficulties with speech-to-text? What are other problems that other people might face if they try to get inspired by doing a similar thing?
Will Croushorn: Again, there [are] 200 billion ways to order a Dave’s Double. If the Dave’s Double has a different ID in one location than another location, it’s not real to the agent. So that takes a different way of thinking in how you structure that data and how you give it to the agent. Drive-throughs are really complex. Real life is really complex. There [are] things like regional campaigns or [a random] snowstorm. So we’re discovering new things every day. We go, “Oh, we need to account for that,” or, “Oh, that’s something that doesn’t exist in the data.”
The other challenge I would say is, and I think every business will go through this, change is hard. Change management is hard. I see this technology. I see where it’s going. I see the good that it does, but it’s almost similar to the first time I drove a Tesla and I put it on autopilot — there’s a trust that you’re letting go. There is so much emotion to trusting these agents and trusting these systems with your business, with your livelihood, with customer satisfaction. And that change doesn’t happen overnight.
So building the right platform is just half the battle. The other challenge is getting everyone else to see: What is the vision? Where is this going? And do I trust this car to drive me down the road?
Sam Ransbotham: Well, so how do you do that then? I agree that it’s a hard thing. How have you tried to work to solve it?
Will Croushorn: It’s looked like a couple of things. No. 1 is having a really great team. In this age of AI, I think the best skill set that anybody could have is a deep curiosity and hunger. I was meeting with some students last week and was talking to them as they’re trying to navigate [things] like, “What do I do with my career?” and “Everything’s changing so fast.”
What’s crazy is one of the things that I’ve started doing … when I’m going down the road, I’ll put ChatGPT on voice mode and I’ll say, “Tell me something new. Help me learn something new.” You have Einstein in your pocket. You have access to information that was not possible even two years ago.
So the knowledge, the information, that’s readily accessible. What’s not as accessible or just apparent are the right questions or being hungry to learn. If you get a really great group of people around you [who] are all asking great, but different, questions or [who] bring different points of view, it makes that product, it makes that experience a lot stronger.
The other thing that I would say we’ve done is, again, it’s not pretty, but it’s just sitting and watching, asking customers. I will get on TikTok, and I’ll just watch. Customers will post their videos of their experience of going through and using the platform. Then a hundred people will comment and say, “Oh, that didn’t work,” or, “That sucks.” And they’ll just post [their] unfiltered thoughts and opinions. Sometimes great, sometimes not.
That’s really, really valuable feedback to go, “Oh, we hit it there. Oh, we didn’t get it there. We need to go back and make that better.” So if you have a great group of people around you and you’re constantly learning, you’re constantly asking questions. My hope is that a year from now, we look back and we go, “Man, that was so primitive. That was so basic. We’ve come a really far way.”
There was a time where I would worry. “Oh man, that’s a hundred-dollar order. I don’t know if it can handle that,” or, “Oh, they said that [was] weird.” I don’t worry about that now. We’ve moved well past that. It’s that building that trust again, [like] that Tesla example of just letting it go and trusting that it can take the wheel.
Sam Ransbotham: Has using artificial intelligence in the drive-through … changed how you measure things? What is different about metrics now?
Will Croushorn: There are those traditional KPIs: check size, speed of service, etc. What has changed is the insight. One of the metrics that we never would’ve looked at before is the number of “sorries.” As we’re looking for friction, well, if the agent or a customer is saying “sorry,” that means something went wrong. That was a new one for us to go, “Oh, wait, maybe we should start tracking that.” So we did this whole analysis. We’ve reduced the number of times the agent says “sorry” by about 60% over the last few months. That’s one of those not obvious metrics, but it’s made a huge impact on the customer experience.
Sam Ransbotham: I love the idea of metrics. Once you say that, it seems so obvious, but it would’ve taken me forever to figure that out. How did you figure out that was a keyword to look for?
Will Croushorn: Again, so much of this is, the more you spend time, you start to see these patterns. … I’ve just spent so much time in the drive-through or interacting with customers or watching. The agent sometimes will say the same phrase over and over, and so you’ll go, “Oh, wait, why did it keep saying ‘sorry’?” Then, “Wait, let’s see. Maybe that’s a metric that we should dig into.”
What’s fascinating in this process, and we talked about this, there’s no rule book for how you build generative AI products and platforms. So much of this is … being curious and hungry, and just like as we spend time, you’re just sort of making the playbook as you go. [You’re] sitting in a room with Google, and their engineers are going, “Well, we’ve never done this before,” and you’re figuring [it] out together. There’s something really beautiful and energizing about that experience. Things like the sorry metric come out of that.
Sam Ransbotham: It seems like you’re approaching this very much from a learning perspective. If we think about the benchmark — I hate to break it to you, but human customer service people are not perfect. You mentioned driving a couple of times. Humans killed 40,000 people last year in car accidents. Our benchmark [for] these technologies is often [that] they have to be perfect on day one, when the reference to that standpoint is nowhere near perfect. So it seems like you’re really approaching that from, “How do we learn from … mistakes? How do we get this right?” Where do you go to get these ideas and to get innovative ideas and new things to try?
Will Croushorn: I am so glad you asked. That is one of my favorite things. I am not looking to competitors. Obviously, I’m aware of what’s happening in the space, but one of the things that we’ve done is we’ve spent time at Disney World. [Walt] Disney Imagineering and Disney Parks have done an incredible job of getting guests in a line to enjoy it. You’re interacting. You’re having fun. Literally, one of the things that’s like, can I get somebody to say, “I want to go to a drive-through” in the same way that they say, “I wanna go to Disney World”? We’re not quite there yet.
Sam Ransbotham: That seems like a pretty hard … a pretty long [way] to go.
Will Croushorn: But I think it’s very doable. Could you pull up an order from your favorite character? Or we’ve already started playing around with Easter eggs, or if you say a different phrase, it’ll unlock certain content in the drive-through.
Sam Ransbotham: I like that. Actually, I hadn’t even thought about that. I’m thinking about, “Oh man, can we get the order right?” That just shows my engineering mind going down the path. Rather, it’s, yeah, put an Easter egg in, or have them talk like a pirate today.
Will Croushorn: Exactly. That’s just one of the many ways that you can put in these little moments of delight that take this thing from being, “Oh, that was really frustrating” to “Oh, that was actually really fun. She was kind of snarky there.” We were at the MIT Museum, and one of the things was research that was done on — I believe it was called NeuroQuery — and it was understanding how typing could predict brain health, Parkinson’s, etc. But it was that type-to-text and the sequences that you see: What does it tell you about how that person is functioning?
So while we’re not quite doing that, literally that visit was an inspiration for, “Oh, wait a minute. We have 150,000 speech-to-text orders. Can you start to see patterns? Can you start to see, oh, they said ‘chicken’ [or] they didn’t say ‘chicken.’ What can you learn from that to make this more efficient?”
One of the things we realized was it takes 12 steps — we call them turns. So I say something, and the agent sends it back. It took about 12 turns to order one of our main menu items. And we said, “Oh, that’s not great. How do we reduce that?” Because anytime there’s friction, it costs money, it causes frustration. Getting down a little bit to the syllable level, we were able to reduce that down to three turns. So it’s a lot faster. It’s a lot more efficient.
The best inspiration is [what] I call [the] what-if mentality. It’s like, go get out of your office, go get into the real world, go sit in that drive-through, go to competitors, go to Disney World, and just be really curious and hungry. It is sort of similar to the iPhone keyboard. I was reading a book recently. It was talking about how [people] had done similar things but not quite like Apple did with the first iPhone, where you have tech typography and art, and then you infuse that with this technology, and then you get this glass touch keyboard that’s actually kind of fun to use, sometimes frustrating. But it was the first of its kind, and it was this mirroring of two different fields. You put [them] together, and that’s where innovation happens.
For me, it’s looking at what is Disney doing? When I’m ordering one touch from Amazon or going to that museum down the street. You have to get out. That’s where those ideas come from.
Sam Ransbotham: How did you get into this? Tell us a little bit about your background.
Will Croushorn: I have the most eclectic background, and it’s something I’m actually really proud of. I did my undergrad in foreign policy. I ended up moving to northern Iraq and doing a startup. We started a school for refugees in the Middle East. [When I] came back, [I] was really interested in products. I’m obsessed with what is that customer interaction like? How can you use these products and technology and software to create, again, that Disney-esque, “Oh my gosh, that was cool. I will never forget.” You’ve created that moment. So when I moved back to the U.S., I started getting more into the product and technology space.
I feel like we’re in one of those opportunity moments right now where every person in every business is trying to figure out, “What do you do with this?” For me personally, it’s my own curiosity on what this thing can do, and it’s led me down this really fun path.
Sam Ransbotham: We have a segment where I’m going to ask you a bunch of rapid-fire questions. So just think about the first thing that comes to your mind.
Will Croushorn: OK.
Sam Ransbotham: What are people doing wrong with artificial intelligence?
Will Croushorn: They’re applying it for the sake of adding AI. There’s no real value add.
Sam Ransbotham: Everything looks like a nail if you have a hammer?
Will Croushorn: Exactly.
Sam Ransbotham: What do you wish that AI could do better?
Will Croushorn: I think be more context aware. Right now, it takes so much work to, you know, if I wanted to respond to an email or I want it to respond to, “Hey, I have this problem,” there’s so much context I have to give it for it to give me the response that’s actually helpful. I think that’s a problem that in a couple years won’t exist. But in its current state, it’s so siloed off that it’s only so helpful.
Sam Ransbotham: That probably ties to our own reticence to share with the technology the way we share with a human. You can’t expect context if you’re not sharing that context at the same time.
Will Croushorn: Exactly.
Sam Ransbotham: Has using artificial intelligence made you spend more or less time with technology in general?
Will Croushorn: I would say I use technology more but in different ways. I find myself on my screen less. I actually spend a lot more time talking and asking questions and learning in a way that I didn’t do. It’s so interesting to go and just see, like, “Oh, I have this itch. Let me go ask it about. …” Yesterday I was asking it about the Cold War and things like that. The sky’s the limit on what you can learn, and it’s right there in your pocket. It’s fascinating.
Sam Ransbotham: What’s the biggest misconception that people have about AI?
Will Croushorn: I think the thought is AI will solve all of my problems and AI is the answer. I firmly believe the fundamentals don’t change. If you’re UPS, it’s, “I need to get packages from one point to the other as fast as possible, as cheaply as possible, and make it great for the customer.” That has nothing to do with technology. That’s just a fundamental value.
For us, it’s delivering fresh food consistently with a great experience, every single time. AI is a new way we can serve with accessibility or with the experience. It allows us to serve those fundamentals in a way that we absolutely couldn’t do before. But that fundamental doesn’t change. It doesn’t matter if Gemini [has] a new model in six months, or OpenAI does something crazy in the next year. It doesn’t matter. That fundamental is still going to be there.
Sam Ransbotham: One of the things I like about these episodes and about this podcast in general is that lots of times I talk to people, and they open up ideas that I’d never thought about before. I certainly had not thought a lot about the drive-through experience, and it’s obviously much more complicated than [I] ever dreamed. But I also like that you connected to the idea of being able to serve lots of different people in a way that they want to be, that’s best for them. Thanks for taking the time to talk with us today.
Will Croushorn: Thank you, Sam. It’s been a pleasure.
Sam Ransbotham: Thanks for listening, everyone. We’ll be bringing you some bonus episodes this winter while we ramp up for Season 13, premiering March 10. Thanks for your continued support of our show, and thanks for listening.
Allison Ryder: Thanks for listening to Me, Myself, and AI. Our show is able to continue, in large part, due to listener support. Your streams and downloads make a big difference. If you have a moment, please consider leaving us an Apple Podcasts review or a rating on Spotify. And share our show with others you think might find it interesting and helpful.