How This $2B+ Technology Company is Preparing for the Future [Ft. Elia Wallen, Engine]
Most important thing with AI is you have to still solve big problems. Talk about AI. From the product side, how are you thinking about it? There's a lot of speculation on where the consumer goes. There's I don't think a lot of speculation around the value of AI and the impact that it will make. It's massive. It's extraordinary. We're seeing it. We've got hundreds of thousands of cases that are now fully automated, right, without any human assist. You've grown this company to this scale without a chief product officer. Is that because you don't think somebody can do it or you don't want somebody to do it? Somebody can definitely do it. But I want flat, man. As flat as we can be for as long as we can be. I wanna know what you're thinking about for the future. Where is your mind going of, like, how to future proof engine? That to me is like We have Eli Wallin here with us, founder and CEO of Engine. Thanks for having me. Alright. So you are founder CEO. You've been around startups your whole life. Your dad, if I ever had, have owned a health food store. Was, like, before Whole Foods was a thing? Oh, yeah. Yeah. Cutting edge. Bleeding edge. He, yeah, he started a couple health food stores down in Naples, Florida. Got up to, I think, three and, you know, not Whole Foods, but think think of that mom and pop kinda little grocery store that they were still helping you pick out which vitamins and brands and things, you know, that you'd buy. So yeah. Yeah. And then you had a couple startups before Engine? Several. Yeah. I was I was the definition of a serial entrepreneur. If I saw an opportunity, I would I would I must have been one of the best LLC creators, generators back then before LegalZoom. I could you spin up an LLC. Yeah. No problem. Now that the statute of limitations is up, you wanna talk a little bit about that casino you had going on in your parents' garage? Yeah. Yeah. That was that that I did not have an LLC for. Yeah. I mean, you gotta you know, we were just kids being kids, and, yeah, we started a little casino, and it grew. We had three tables at one point, and we were not just, you know, playing playing blackjack, but we were selling stogies and beers to, you know, other things. Yeah. Was fun to Alright. So fast forward, here you are, Engine Now travel management. You wanna give just a little explanation of what Engine does? Yeah. Modern travel management platform. Yeah. Yeah. Built more specifically for for the SMB. Great. And for those who don't know, I worked at Engine with you for a while, so that's exciting. We we go That's awesome. Way back. Founder mode was huge. I remember a couple years ago, remember us reading about it. Was, like, one probably my first week or two there, that article I think had come out, and you're kind of the definition of it. Here you are with over a thousand employees at Engine. Can you actually live founder mode at that scale? Yeah. I I don't think the founder mode I mean, it it kinda got torn apart a little bit post coming out. I think everybody you know? But, ultimately, I think when when you break it down to just the the basic principles of what it mean, like, staying involved in the business is something that's we've we've done, I think, very well. You gotta live in the details. You lose the details, you lose everything. And I think for us, that's just what we've done. And I think founder mode, and and again, in the purest sense, is is trying to define that, staying close to things, not building these layers in the hierarchy. So, yeah, with a thousand people, it's absolutely I mean, absolutely, without question. I think all of the execs of a business, all the managers, I mean, everyone needs to understand the business deeply. And I don't think that that was maybe historically what happened as much, but you you look at history and the people even Rockefeller knew every single cent and dollar, you know, every point of his business. And, yeah, time and time again, like, that's that's where it works. So early on, No Rules Rules, the Netflix book was wildly, like, embedded in the culture. Yes. Right? A lot of that relies on having people that are really accountable, stream ownership in a lot of cases. Have there been pain points as you've grown, like, trying to live that philosophy? Yeah. That takes multiple ingredients to pull off, right, that that type of culture. Talent density is one of them. Talent density. And you don't get there overnight. And I think as you start to pull back rules, you can only do that when the talent density of the organization starts to grow. Yeah. I mean, it's it's it's tricky, and you thread the needle, and you remove some, you know, rules and restrictions, some barriers, but, you know, you kinda do it over time. It it's not something that just happens overnight. All of sudden, like, freedom and responsibility for everyone. Let's go let's go. Y'all, you know, full agency with everything. But it is cool to see the evolution, no doubt. And and I absolutely am convinced that's the way to build an enduring business. Okay. So speaking of talent, you've gotta hire a lot of people, now over a thousand employees and growing fifty, sixty percent year over year. Right. You've gotta hire, I'm sure, a ton. So you're doing a lot of interviews, guys doing case studies, which I love. It's like one of the things that I've I've always gonna take from engine and never hire anybody without having to do a case study. So that was one of the best learnings I had. But when you think about the talent of who you're going after, and are you looking for scrappiness? Are you looking for they've seen this movie before. And has that changed as the company has grown? Yeah. Look for different people at different stages. Yeah. I would say, you know, somewhere in between ambition and experience, and some people can have the experience and keep that ambition and keep that hunger and drive. I think it becomes more and more rare. For us, we're still in absolute builder mode. Like, we I want people to be in the business, and I think as you try to find people that have done it before, it's harder to find those people that still want to get back into the trenches with you. And so I've always preferred finding up and comers. People that are still extremely hungry, chip on their shoulder, want to have something to prove. I would just say that will is much, much more important than experience because the world's changed so fast. The experience they had ten years ago, five years ago is simply you know, a lot of it may not be transferable. Okay. So company's growing quickly. Twenty twenty one hits. You did a series b at the time. Got unicorn status, one point three billion. How'd it feel? Woke up. Everything was not much different, man. A little bit more money in the bank, not much more, and, you know, we just moved forward. It it it wasn't this game changing thing. It wasn't for us. It was it was a great milestone. Right? Do a quick victory lap, small with the team, and then you just move on. You know, I was there for the series c twenty twenty four. It was Premira led it, two point one billion valuation, which, you know, you'd look at the the math and someone from the outside goes, okay. One point three billion in twenty twenty one versus two point one in twenty twenty four. Okay. They're they're, you know, doubling a couple years. But, realistically, when you look at the the actual valuations, right, the multiples that you were getting in twenty twenty one at thirty x versus nine to ten x in twenty twenty four, you might have really been a four million four hundred million dollar company Yeah. In twenty twenty one. So the growth is is unbelievable. We should've I don't like, I guess my point is I don't even remember the victory lap. I don't know. We must have sent a Slack or something out. I'm sure somewhere there was some sort of little thing internally. High five. That wasn't yeah. I mean, that that wasn't the point of the raise. Right? And and I think going back to your point really quick, the raises in twenty twenty one, anyone else that raised the next following years, most companies had a flat or down round. So, yes, I I do think that there's something underneath the numbers that show on the surface it looked like maybe a double, but it it was much more than that for us, certainly. Okay. Now company is, I mean, that was twenty twenty four. You guys are growing so fast. Company is probably valued in the the threes. Who knows? You know, next round will probably show higher. That's what I'd like to think too. You've done this. You've grown this company to this scale without a chief product officer. Yeah. Is that because you don't think somebody can do it, or you don't want somebody to do it? Oh, somebody can definitely do it. But I I want flat, man. I I like we have an incredible product team. Giving them the agency and the ability to get into the business and make the decisions while I can stay close to it while the rest of the business can stay close to it. I think those layers, even at that level, it's another layer. I man, as flat as we can be for as long as we can be is the path that we're choosing. And, you know, I think you're starting to see more and more companies do this. You're seeing middle management layers start to get removed, especially with AI and the the speed in which businesses and teams can operate when you don't have people in the way, actually slowing it down, decision by committee, bureaucracy, all this stuff. For me, Flatter is better, and in this case, like, we've got a great product team, we're moving very quickly, and, yeah, I like where it is. Of all the board meetings I joined at my time at Amgen, every one of them had some part of it focused on how do we get Eli to have less direct reports? Yeah. How many do you have now? Fifteen. Okay. What's the most you've had? Twenty five. K. Wild for for most people to to think about. What about the one on one structure? We have I remember this being really an interesting point of view from you in terms of just, like, a lot of one on ones are done, like, check ins. Right? But you don't see it that way. No. I mean, I I think for me, like, we've got a talent dense organization. We've got great people, and they know the mission. We are mission first. We're focused on delivering the goods there. And so I think my job really is to help unblock these folks and help them see blind spots. There's all these benchmarks and rule of seven and all this stuff with direct reports. Like, literally all of that to me is noise. And some of it works, some of it doesn't. It doesn't mean that you can't learn from the history, but it doesn't mean you have to repeat and copy it. And so for us, I think we do things that work, and if it doesn't work, we change it. And, yeah, twenty five direct reports operating kinda how it is, it's probably not the best for the business. But, you know, this this whole concept that you have way too many, like, where is that rationale? Where where how are you coming up with that assumption? Because another company in the app doesn't have it? Like, I don't I don't buy it. Well, he could truly operate like that, where everybody who reports to you is coming to you for your one on one with an agenda. They're talking at you, not you being like, how are things going? And they're going, here's where I need unlocking. Then adding that extra layer in between only serves to that person and now have to ask you potentially, right, if they if they wanna check-in. It's it's maybe even more inefficient to have that. If ninety nine percent of things are going right, wouldn't say about the one percent wrong. I mean, that's what we spend our time on. Those problems, I wanna obsess about the problems. And I think that's what the team does pretty well, and that's what those one on ones are for. What's what's the issue? How are we gonna solve it? And let's move on to the next issue and make it very, very comfortable to talk about. Speaking of problems, you know, there has to be points in the history of where problems became really big. Yeah. What's kind of the lowest low you can think of in the company's trajectory? Yeah. We were just chatting about this. Like, business is problems. If you don't like that business, get out of business altogether. Like, you're in the business of solving problems, of dealing with problems every single day, and problems happen all the time. So I don't some bigger than others, but at the end of the day, sun's gonna come up tomorrow, you gotta solve it. And so for us, though, less about problem, more about fear. Obviously, we we I have maybe healthy paranoia, maybe maybe a little bit unhealthy. But I think the way that I think about it is one of the worst challenge most challenging times for us is we were about to run out of cash right before we raised our series a. How close? Weeks. Vapors in the tank. I mean, there's not much left. How many employees at this point? So this was both companies. So this TravelSaven and Engine, I don't know. There's probably hundred and fifty, hundred and eighty of us a while back, and it it got really scary. And I remember calling friends, asking for money, and being turned on even though I had a couple successful businesses. It was risky. And luckily, the series a was delayed by a week, freaked out. It closed, and we we you know, disaster was averted. And that was Telescope. Yeah. Yeah. Telescope. Mickey Arabella. Yeah. He was Like, I think he might know that story now, but we were we were down to the wire. And he had some leverage over me probably that he didn't know about, but he could've he could've maybe tightened the screws, but he didn't, of course. A great guy, and and we closed, and, you know, the rest is history. One thing I think other founders might be interested in in hearing is your point of view on investors. And, I mean, everybody who has who's invested is minority at this point. Right? So everyone's minority. You got Blackstone, Telescope, Elephant, Premira. Right? How do you like, when you're choosing because you are in a position where you can choose. Some founders are in positions where they they have to take who's there, and you got really lucky with Mickey. I think Mickey's an amazing person. Telescope's awesome, and, you know, you you were at the wire and you ended up going with him. That's great. But I remember a story you you telling just about how Mickey kind of impressed you when he he came in. Can you tell us about that? I'm insanely fortunate for my, you know, first real primary investor to be Mickey and Telescope. Cut from a different cloth, you know, he was all about alignment and creating value, not what can I extract, how can I how can I get an angle on this? And he's still to this day. You know? True is the day is long that he's he's all about helping create value, not judging. There's no dysfunction. It's crazy lucky that that was my first experience, and, you know, then he led the series b, and, like, so that pays off in a sense. Right? Like, he's such a great guy, gets money in early, and you wanna work with him, you know, it was the easy button for us, you know, as he describes it. So the series b was the easy button, and Blackstone came along in that race. But, yeah, very, very fortunate that that he came along when he did. Let's move on to AI. How are you thinking about this? Engine is a travel management company. Businesses are using it to book hotels, book flights, book cars. I still use it all the time. Just getting it in at at Cadre, used it for this trip. I know. So Yeah. Let's go. Saves a ton of money, but you've got big competitors who are I mean, I don't know that there's so much competing in the the small business space. You got Expedia, you got big travel platforms who are probably throwing a lot into how AI is going to improve the travel experience. Yeah. How are you thinking about it at engine in terms of AI on the product side? A lot. I mean, we're we're literally thinking about every interaction with AI, both customer facing and internal. There's massive, massive opportunities. Like, I'm not saying anything that that people don't already know. I think, though, that the big thing is gonna be customer adoption and behavior. And we're actually gonna see today, which is kind of strange, like, you're not seeing a ton in the shopping experience, really in any travel spot. I mean, certainly, there's there's some of these, you know, smaller things that are popping up here and there, and maybe there will be some traction with it. We'll see. Time will tell. But I think for us, it's more about personalization and going to where the customer wants to be. You know? So so I think you'll see us do more with voice. I think you'll see us do more with chat. You'll see a lot more personalization, significant personalization around just like, we know what you want. Let's just stop the madness. Right? You don't need to scroll. You don't need to search. So I think you'll start to see more and more of that, and we'll there's it's just massive testing that's happening in the background that I think will ultimately take us where we wanna go. Internally, when you think about the you got the product side, AI folks. Do you have a AI focused team on the product side who, like, that's all they're folk thinking about, or does the travel and the groups and each, you know, individual section and product have its own kind of view on AI? Our thought process is every person and product of the company needs to understand and be willing to adopt and think about wake up every day and think about AI and how it's gonna transform and change. It's interesting. As we hire folks, like, it's still so new. There's still a lot of people that are uncertain about it. Like, there's still people that you have to break these habits. Even age doesn't matter what they've been doing. You know? It's like, it's still it's interesting. You know? But, yeah, I mean, every every person this is gonna be a core core part of their function, right, is is to think through an AI lens when they're designing and building net new features for our customers, and and obviously, the historical features that we've built. Then you got AI able to deliver efficiency with the team. So just whether that's, you know, people doing more with less. Yeah. How are you thinking about AI when it comes to, you know, the people internally and making those workflows more efficient? Do you have, you know are were there lessons learned? I know at some point we had IT kinda focus on AI. I think now it lives in a different department in in engine. So what do we learn? Seeing a lot more velocity or acceleration growth there. The the reason is the user test, it's small. Right? This is our team, and we're getting real feedback immediately on the things that we're changing, and we know what's to change. Like, we have all the data on every one of the processes of every person in the company, so we can see and make those changes very, very rapidly without worrying about what customers we're gonna alienate, what customers wanna adopt, what customers don't wanna adopt internally, we literally can just we can run that play a little bit more aggressively, and we are in massive, massive improvements and changes in efficiency. Where any departments you've seen it work better in than others? I mean, certainly on our client op side. Right? That's that's the that's the easy one. Think most people that are calling what we've seen, you know, we've got hundreds of thousands of cases that are now fully automated, right, without any human assist. Yeah. Take it. Yes. That's right. I gotta change my flight. Yeah. I have to Yeah. Didn't get my points. That's right. Over fifty percent of our cases now are done without any sort of human assist. And, yeah, and so, I mean, those those are the things that you can roll out pretty quickly because what we found, CSAT is actually a bit higher too when our customers are engaging directly with AI because, really, it's not about they just want their problem solved at the end of the day in the fastest, most efficient way. What we have, though, there's some scar tissue of some of these old school automated, you know, prompts in in the phones when you call, like, it couldn't help, couldn't help, couldn't help, and then you say agent or let me speak to a representative. Like, that was the first thing we'd do when you'd hear that. So, you know, there there's some of those folks that, you know, we've we've experienced that. And so you got some of that scar tissue to to overcome, but it's getting there. Right? And people are becoming much more comfortable with this newer, more modern version of of, yeah, agentic help. Do I remember it correctly that there was a time, and maybe it's changed by now, but there's, like, something like fifty thousand inbound calls, chats, emails, whatever coming in, and at the time, there was a team of humans that were just reading them and then saying, that should go to this team. That thing Yeah. This team is solving anything. Yeah. Routing. Yeah. Wild type. Oh, yeah. Yeah. Yeah. Well, I mean, yeah. These are these are some just reading, categorization, teeing it up to the yeah. That that's all done. I mean, a lot a lot now is is fully automated. It's very interesting to see CSAT scores improve, and you can put those folks on more I mean, the the the good thing for us is, like, you know, the business is doubling. Right? We're growing very fast. And so there's more and more of those high value touch points that we still need humans for, and we will, you know, probably always maintain an element of that, like, if we want that true white glove experience. And so that's a really brand decision, and I think we're all in on that. And so, like, we're we're in a fortunate position that, you know, we can move those folks, repurpose, redeploy on on some of those those other key areas that are continuing to need human assistance. At Engine, I remember hearing people say this a lot, you know, the world's different in a month and two months. Planning too far ahead felt just silly because things change so quickly, and you've got to have that kind of growth mindset of like, give me the problems, and let's let's go where the problems are and fix them. Having said that, I wanna know what you're thinking about for the future in terms of, like, if you fast forward to twenty thirty or you're trying to future proof the business in some way, like, where is your mind going of, like, how to future proof engine for Yeah. Whatever year it is, twenty thirty? For one, I'm just I'm planning really quick. People don't understand the complexities of the world if you try to make a five year plan and stick to it. And that that to me is, like, such a a crazy concept. I mean, if you go back a couple years, like, that is how business was done. You know, I I'm I'm glad. I'm hopeful to see less and less of that structured, rigid planning rollout, and it's gotta be modern. It's gotta be fast. It's gotta be agile. So anyways, I think I think the world is starting to catch on to that, and I think that you'll see fewer and fewer. What's it gonna look like in five years? My crystal ball's broken. I mean, I I don't think anyone can tell that answer. I don't care how good of an expert you are, so let's stop trying. Right? And let's just start to like, new information comes in, change your mind. It's fine. And if everyone can just rally around that, I think you're the the business will be in a much better place. So we really try to drive that home that don't get too married to any of these any of these decisions because they most likely will change because the the world is changing faster now than ever before. And that's something you live. I know it because the the term we've used is strong convictions loosely held. That's right. I have heard you say convincingly multiple times, we will never do flights and cars. We are a hotel booking platform. We're gonna be the best in the world at that. That's right. And weeks later, you know, I'm writing the the script for Summit. Yeah. You know, with our all of our employees, and it's like, oh, by the way, throw in something about you know, they're like, plus, we're doing flights and cars. Like, oh, okay. Yeah. That's a mindset that you live by. Right? Absolutely. Yeah. We have to. And we'll get it wrong. We won't get it all right, but certainly, I think with that mentality, you're not gonna be caught flat footed. Right? You're not gonna be in a position like, oh, shit. How do we get out of this now? I think everyone in the business needs to be entrepreneurial. They need to be thinking about those problems, the paranoia. We're gonna fail if we don't, you know, adapt quickly. Everyone just has to believe in that. And I think when you do, you have less friction. There's less stiffness. Right? It's hard about, like, not letting the old man into the business. I did this this morning with the company. Letting the old man in, you get stale, you get stiff, you get rigid. And so we gotta keep bureaucracy out. We gotta keep layers out. It's we've gotta stay young as an organization. And as you get bigger, I mean, even Amazon. Right? Like, day one mentality. Right? And, like, everyone tries to do that for as long as they can, think, some companies more successfully than not, but we're still deeply entrenched in we got we gotta stay young as an organization even though we're growing. I wanna cut process. I wanna delete everything that we can delete all the damn time, rethink the road map, rethink how we approach the problems we're trying to solve because it just these problems change every single day. Yeah. And when problems come up, what do we say? We say good. Right? Good. Anyone who hasn't seen that Jocko good Google, Jocko's good. Fantastic. Yeah. We played it at summits. We we played it all the time. It's, you know, you get a problem, something's going wrong. Yeah. It's opportunity to fix it, opportunity to get better. And that's what you're going back to earlier, just like focus on the problems, not the good stuff. And that's probably why I don't remember a celebration at any of the They weren't in any. The big rounds. No. Focus on the past. Yeah. Cool. Eli Wallin, CEO and founder of Etude. Thanks for coming by. Thanks, buddy. Appreciate it. Appreciate it. Thank you.
Most boards pressure founders to reduce direct reports as they scale. Elia Wallen took the opposite approach: he manages 15 direct reports while growing Engine past 1,000 employees to a $2.1B valuation, and he eliminated the Chief Product Officer role entirely. His logic: additional management layers slow decision-making when speed matters most. When you build talent density and restructure one-on-ones around problem-solving instead of status updates, you can operate with higher spans of control.
That philosophy was nearly tested to breaking point. Engine came within weeks of running out of cash before their Series A with Telescope Partners closed. At the time, they had 150-180 employees across two entities. That near-death experience shaped Wallen's rejection of rigid planning. He refuses to create five-year plans, preferring to pivot quickly when new information emerges. Case in point: he publicly declared Engine would never do flights and cars, then reversed the decision weeks later. On AI, they've now automated over 50% of support cases while actually improving customer satisfaction scores—not by replacing people, but by redeploying them to higher-value work as the company doubles annually.
Topics discussed:
Engine is the modern travel platform for booking and managing work trips. It saves businesses time and money through an intuitive travel network that connects to nearly every hotel, airline, and car rental company in the U.S. It offers single invoice billing, the flexibility to modify trips at any time without sunk costs, and a unified view of all company travel and spend. Customers rely on Engine to not only make travel easier to manage, but to make it enjoyable for everyone involved. The company is backed by Telescope Partners, Blackstone, Elefund and Permira.
You think about the talent of who you're going after, and are you looking for scrappiness? Are you looking for they've seen this movie before. And has that changed as the company has I've grown? Yeah. Look for different people at different stages? Yeah. I would say, you know, somewhere in between ambition and experience, and some people can have the experience and keep that ambition and keep that hunger and drive. I think it becomes more and more rare. For us, we're still in absolute builder mode. Like, we I want people to be in the business, And I think as you try to find people that have done it before, it's harder to find those people that still want to get back into the trenches with you. And so I've always preferred finding up and comers, people that are still extremely hungry, chip on their shoulder, want to have something to prove, and then they'll figure it out. But I for me, will is is the thing we have to stick with.
You've grown this company to this scale without a chief product officer. Is that because you don't think somebody can do it, or you don't want somebody to do it? Somebody can definitely do it. But I I want Flatman. I I like we have an incredible product team. Giving them the agency and the ability to get into the business and make the decisions while I can stay close to it while the rest of the business can stay close to it, I think those layers, even at that level, it's another layer. As flat as we can be for as long as we can be is the path that we're choosing. And, you know, I think you're starting to see more and more companies do this. You're seeing middle management layers start to get removed, especially with AI and the speed in which businesses and teams can operate when you don't have people in the way, actually slowing it down, decision by committee, bureaucracy, all this stuff. For me, Flatter is better. And in this case, like, we've got a great product team that we're moving very quickly, and I like where it is.
People don't understand the complexities of the world if you try to make a five year plan and stick to it. And that's that to me is, like, such a a crazy concept. I mean, if you go back a couple years, like, that is how business was done. I'm hopeful to see less and less of that structured, rigid planning rollout. It's gotta be modern. It's gotta be fast. It's gotta be agile. So, anyways, I think I think the world is starting to catch on to that, and I think that you'll see fewer and fewer. What's it gonna look like in five years? My crystal ball's broken. I mean, I I don't think anyone can tell that answer. I don't care how good of an expert you are, so let's stop trying. Right? New information comes in, change your mind. It's fine. And if everyone can just rally around that, I think you're the the business will be in a much better place. So we really try to drive that home that don't get too married to any of these any of these decisions because it most likely will change because the the world is changing faster now than ever before.
I think everyone in the business needs to be entrepreneurial. They need to be thinking about those problems, the paranoia that we're gonna fail if we don't, you know, adapt quickly. Everyone just has to believe in that. And I think when you do, you have less friction. There's less stiffness. Right? It's hard about, like, not letting the old man into the business. I did this this morning with the company. Letting the old man in, you get stale, you get stiff, you get rigid, and so we gotta keep bureaucracy out. We gotta keep layers out. It's we've gotta stay young as an organization. And as you get bigger, I mean, even Amazon. Right? Like, day one mentality. Right? And, like, everyone tries to do that for as long as they can. I think some companies more successful, but we're still deeply entrenched in we gotta stay young as an organization even though we're growing. I wanna cut process. I wanna delete everything that we can delete all the damn time, rethink the road map, rethink how we approach the problems we're trying to solve because it just these problems change every single day.

