Bridging Human and AI Solutions - Ryan Wang - Assembled - Episode #71

I just thought break the company in terms of trying to do too many things. But it turns out breaking the company in terms of culture is a very real thing.

Welcome to Not Another CEO Podcast. I'm your host, David Politis. Every week we talk to inspiring leaders and get the true stories, the ups and downs, the lessons learned and come away with actionable advice for our own journeys.

Today's guest is Ryan Wang, the founder and CEO of Assembled. Ryan and his co founders, one being his brother John, started Assembled to solve one of the biggest challenges in modern customer support. How to scale operations without losing efficiency or customer experience. What began as a simple scheduling tool has grown into a category defining AI customer support platform that is trusted by leading companies like Doordash, Salesforce and Ashley. Furniture Assembled has raised over 70 million from top investors including NEA, Emergence Capital, Stripe and more. The company has become a go to solution for high growth teams, combining deep empathy for support organizations with a product first mindset. With that, please welcome Ryan Wang.

Good to be here. Thanks.

Excited to have you. First question, first question I ask everyone, what is the one thing you've done at Assembled, big or small, that's had the biggest impact? And you do again if you're CEO of another company in the future.

Yeah.

When I talk to founders that I look up to and want to learn from, one of the first takeaways is that they're just surprisingly in the weeds and the details. And for me, the specific thing that I do and would do again is just to keep getting deep into the weeds and in particular leading different functions for a month to three months at a time. I think the shorter the better. But you know, I was at a customer success conference in New York just yesterday. I'm interim head of customer success. And I think one of the things that happens when you get that deep into the function is you're forced to really understand what is really going on. What are the challenges? Who are the folks that you're working with? What are they running into? What are their abilities? You know, where are they going with their careers? How can you help them?

And there was something that, when I worked at Stripe that Patrick and John Collison did as well, which was, you know, anytime they were hiring, they would go ask, what does great look like in this function or in this role?

And when you're leading it, you're kind of forced to go ask that question. You can go seek it out. So you go find the. When I was doing engineering, the first VP of engineer at Airbnb, Mike Curtis, and go pick his brand. Like, what did it look like when you were scaling up Airbnb? First up of engineering at Facebook, Mike Vernal. What did that look like with Facebook? And you kind of hear them talk. And Mike Vernal had this example of, from Magic the Gathering, he described people who were dual lands. They could do this and do that. They had multiple superpowers and both. That gives you a picture of.

How they operated, but also how they think. It's very evocative that they've got this engineering leader using Magic the Gathering references. So you start to piece together. Yeah, what does great look like? And you carry it into the function. And then, and then you. Of course, when I say you don't want to stay there too long, it's. There are people who are much better at leading customer success teams, leading engineering teams and so on. Like, I'm not pretending that I'm the world's expert. I'm trying to learn from them to get a mental model and that. Bring somebody in to take care of the function and then, and then you move on. But then you have a clear sense of.

What is actually happening here. And maybe you cycle through when things change over time. But right now, over the last year, two years of building out our executive team, that's been the MO is learning deeply and then bringing the right person.

So a couple of people have said, wear every hat, do every job, go deep in these different things. You're the first person to say, go find, go talk to the best of that function. You're the first person who said that. And I, I literally, like, I love that so much.

How do you get in front of those people? I mean, the people you're talking about are like, these are not easy people, at least I wouldn't think to get in, in touch with. Like, how do you get in front of them?

Yeah, I'm, I, I think that.

The, the, the, the surprising thing about people who are the world's best at something is that they are way more approachable than you think. I think in this customer success conference, you know, we had the SVP at, at GitHub, we had the head of Customer Success at Notion, we had a woman who runs Customer Success at Vanta, and, and I had talked to her, Kelly Bray.

Actually over Zoom, you know, before the conference. And it was a friend of mine who had a, another friend. And this is when we were doing marketing. So, so this woman, Nami, who had worked at Slack Run Product Marketing at Slack Run Product Marketing at Ramp, she had worked together with Kelly. And, and because I had picked her brain long ago on product marketing, I said hey, you know, can you give me an introduction to Kelly? And, and, and she was up for. Because we, we had had a positive interaction. I learned a lot from Nami and we'd worked together on some projects. So, so these things I think are compounding. The more that you find people who are interesting to learn from and they can tell that you're genuinely interested in learning, they're much more willing to, to open up their networks. And so I've definitely found it wasn't like on day one, it was, hey, I've cold outbounding, you know, Mike Curtis, can you give me 30 minutes of your time? But, but working through people that you know and like slowly growing out the network. And then I think the other thing too is that people can tell when you're really trying to learn. Like nobody wants to network, nobody wants to just waste their time. So with these people, you know, I tell them, hey, here's a 15 minute calendar link. I'm gonna make it super easy. If you'd prefer that I call you over the phone, I'll call you on the phone. If you want to talk on Saturday, I'll talk Saturday. I'll talk to you at any time. Right. And, and I'm going to have all my notes ready to go and what exactly I want to learn and so people know I'm not wasting their time and I think that contributes to it too. It's really great. People are generous with their time, but they just don't want you to. They don't want to be sold something, they don't want you to waste it. They want to know that it's valuable.

That part about that's very good. The tactical advice there, which is when you're reaching out to be explicit, I'm going to work around your schedule is what I hear you saying. I don't care when that is. Day, night, weekend, doesn't matter. And I'm not going to waste your time because I'm going to come prepared. But I really do want to learn from you because you're the best at it. And what you're saying is people will respond to that message because it's, they feel like they're paying it forward, they're helping someone who really wants to learn. But that tactical thing I think shouldn't be glossed over of if you're going to do that, you have to be ready to kind of do whatever is necessary to make it easy for them.

And every single signal, you know, because they'd probably get a million emails, they'd probably have a million people come up to my conferences with questions where they're just trying to sell them something or and you can instantly see because I've tried to sell people things, you know, at conferences as well, you can tell. Oh and by the way, here's what assembled a, you know, the wall goes up. But if they can detect. Genuinely I'm trying to learn. People are very, very generous and so every signal is around like I'm trying to learn. I'm, I'm trying to move quickly. I'm not going to waste your time.

It's good advice and something I wish I did actually because I think I made many mistakes myself in hiring and I've seen other people because you don't know what great. Especially if it's the first time you're hiring for that role. How would you know? Yeah, what it looks like, you know, and so having those conversations I fully you, you see in those people, you meet a couple of them and you say oh wow, now I see I may, I'm not going to get that person probably. But at least I understand what I'm.

Shooting for for sure. And, and, and even to circle back to the, you know, going through functions I find that the most valuable thing like sitting with customer success, sitting with engineering, the most valuable thing is to raise people's eyeline to say hey, this is how I hire. You know, I go out and find the world's best at X. And so you know, we have a bunch of new people in our customer success team who are first time managers. And I think the most valuable thing I've left them with is not you know, here's how to do the customer journey or here's the KPIs to measure. Here's how you multi thread. It's rather, hey, when you're going to hire, don't just try to find the person that fills the role. Like do the same thing that I'm doing. That's the thing that I'm trying to leave them with. Run this process of understand what great looks like and for you it will be different. But here's how you do it. And when you really tell people I want you to go meet the world's best, then it leaves them with a very clear picture of what we're going for.

Now when you talk about jumping into these different roles again, having done this before, it's not that easy to become the interim. I mean you have a real Company at real scale. So when you become the interim head of whatever, how do you do that again, tactically, time wise? I mean, do you. You're doing the CEO job and you're doing this other job. How, how do you handle that? How do you, how do you do that?

Yeah, it takes a lot of time. It's really painful.

Ron. It's. It's not, it's not fun. I mean, it is fun, but it takes a long time. And I think, and I think for other people as well, it's difficult. So for people on a team, you have to be able to recognize that, yeah, like, you inhabit this role, like I inhabit this role, CEO. And so things that I say, people listen to in a particular way. And so, you know, I try to, I, I try to signpost a lot. So, hey, I'm wearing my customer success hat. Hey, I'm wearing my engineering hat. I'm not talking to you as the CEO of Assemble. I'm talking to you as your peer and head of customer success. I'm talking to you as your kind of direct manager, not somebody punching through the wall. It only goes so far because people, you know, like apartment pie so much, including myself. But I think to the extent that we're able to compartmentalize and say, yeah, I'm talking super, super tactically, I want you to push back on me. I found that that's really important.

I think helping set people's expectations around timing. It's like, this is not, we're not going to do this forever. We are going to go higher ahead of customer success. Part of what I'm doing at this conference as well was building my network and sharing out with people. Just like the thought process of, where are we at in this function, in this organization, in this company? I found that that's really helpful because, yeah, people want to know, like, are you going to do this forever? Don't you have a day job already? Should all the rest of us also be doing two, three, four different things at a time?

But I think the biggest one is around decision making and helping people come to their own decisions and not bulldozing through them. Because by default, almost every single meeting is a skip bubble meeting.

Right.

Of all the functions you've done, dug deep into, what is the one you've surprised? You've been surprised with how interesting it was or how much you enjoyed it?

I think every, every single one, I've, I've taken something away. I mean, I'm the type of person who, you know, went to college to study Economics and ended up with a degree in statistics and worked at a management consulting company where I was actually a data scientist and became a software engineer. So I just like jumping around and learning new things.

But I would say that.

With engineering, I was surprised by how much of it is classical people management challenges. Helping people find focus, helping people figure out to tie their personal career development to the needs and impact of the business.

Helping them figure out how to work together better. You know, I think when you think of engineering, it feels like this very different world of different cast of characters. Right. Different types of personalities, different way in which they're working. But, but at the end of the day, the commonality is, is, you know, it's a team of people.

So, so if anything, engineering management is essentially management management. And, and I think across all the functions I've worked in, maybe that's been the surprising thread. Like you get to. Yeah, the specifics of the function. But management is management. And helping people work together well and motivating them, that's a universal challenge.

You know, as you're saying all of these things, I'm thinking about some of the best people I've had in my entire career who have moved across functions as leaders and been successful in multiple functions. And you do actually realize that.

I.

Mean, other than engineering, I definitely could not run engineering, but other than that, you know, maybe, maybe, I don't know. But other than that, you know, there's something about just being curious and getting your hands dirty and, and being a good people manager and if you put those things together, of course there's, there's domain expertise and everything else, but it's surprising how much you can, you can get done. And I think a lot of founders get very scared to go in the areas that are not their areas. And I, I think it's a big mistake, 100%.

And isn't it ironic that, you know, part of the job which is all about get yourself uncomfortable is, well, I need an expert to, to handle.

It helps when you don't have a choice as well.

Right, Right.

If you don't have a choice, then you have to do it. You learn pretty quick.

Yeah. At one point I took over sales at Better Cloud and I had, remember, 1012 reps reporting to me, which was crazy because I had my rest of my job. But I learned so much. I learned.

And this is at a point we're already scaling, so I, I needed to learn things about how Salesforce was set up and how activities were logged and opportunity stage gates that, you know, at some stage get further away from that. And then you get in, you go, why do we do that? That takes 10 extra steps. That's a really stupid button. You know, you start to go into the, the weeds of it and you say wow, like this. And I think that is what maybe people get. You said it earlier, you said you kind of dove in, but only for some period of time and then hired someone and pulled yourself out. And I think people sometimes confused when they, I think when they hear the founder mode story, they think it means be in the weeds of, of everything all the time micromanaging. And that's not actually what we're saying.

You can't. Because if you had 12 AES and you're trying to, to scale that up, I'm guessing just every single day that you, and not another per, you know, a true world class sales leader or doing that, you can see the opportunity cost and maybe see the kind of money getting lit up.

So you didn't start as CEO of assembled, you stepped into this role. Talking about, talking about a role to step into. So can you talk a little bit about how that came about?

Yeah. The company had three co founders, myself, a fellow named Brian Z who was the first CEO, and then a fellow named John Wang who's my brother. So from very early on we had this interesting kooky dynamic. I think.

John was at mit, worked on Ruby on Rails, engineers. Engineer Brian was one of the first salespeople at Stripe before they even called it sales. I think.

Biz ops and biz ops would do anything and everything and then I was kind of in between. I was working on code. In the early days with Sembled I had been a software engineer at Stripe, but I didn't start that way. And so we had this kind of nice balanced co founding group in terms of skill sets. So very early days it made sense. Well, in the very, very early days we didn't have a CEO. Just yeah, it's like what's the point? We'd never been asked that question. We're just trying to, you know, build the product and get it to market. I think right around, right around our seed route. And after we had a couple customers, it made sense to have a CEO and it made sense for Brian to be that CEO. He was the main seller, he was the go to market person, he was the face of the company.

And shortly after our Series A, which is I think jarring to our investors, but I think it's worked out for them, shortly after our Series A, he decided, you know, what.

He had a good run. And he said as I was thinking about what would be best for the company, I realized on Sunday night I wasn't thinking about what is going into the week, I was thinking about other things. And we need somebody who's going to think about the company at all times. And so I think it's time to trade spots.

I thought that was a really incredible thing for him to have done because just the self awareness and especially at that time, right after we'd raised around, I was like, wait a second, if we want to get to the next level, actually we need this trade seats.

So I was in Manhattan beach, walking on the beach when I got this phone call. Oh, wow.

That'S big.

But it was executed pretty quickly and pretty seamlessly in the sense that we, I would say had had ongoing conversations over time of just roles and responsibilities. And I had always wanted to be CEO. I'd always wanted to test myself in that way. And I thought that there were things that I can do in the business that other people couldn't. And so for example, our, our first executive hire, also highly unorthodox, where we had hired a head of marketing. We'd worked with an exec search firm. Brian was CEO and I had been working on marketing. And we had this conversation really early on which is like, I think I should be leading this search. The search firm told usually the CEO is hiring the executives, they're building out the executive team. I don't know how we're going to explain this to people. And our argument at the time was, well, we were 10, 15 people or something like that. The right person won't really be worried about that kind of reporting structure that just be willing to jump in. And you know, I think in retrospect it probably would have made more sense for Brian to leave that search. But again we were, we had this kind of dynamic where we could kind of work through these types of things together and ultimately just ask, you know, what's best for the business. So we did find somebody who fit that bill and who.

Ended up staying with the company for four years as our first executive.

Past like a 30x or something in revenue and you know, much, much longer than the typical executive. And I just remember when we gave her the offer, Brian was CEO and by the time she joined.

That kind of sort of came closer question.

Was.

She surprised when she, when she started or not really?

I think she was surprised. She was pleasantly surprised. And the way that the search firm said, you know, well, you know, this is only Good for her.

To make things easier.

Yeah. What do you think? You said, you know, you always wanted to be a CEO at some point in time. What do you think is the part of the job that's.

Harder than you expected it to be?

So many things. I. I think it's a very particular job, and. And it's difficult in its own ways. And I'll tell you that when. When Brian was CEO and I was not CEO, we would get into all these arguments about what should happen in the business. For example, you know, who should lead this. This search, you know, on the executive hire. And.

One time we were in New York, like, walking all the way down from Times Square to where we were staying. I think it was a Tribeca or something, visiting a customer. And we just had this enormous argument. I can't even remember about what, but it was something to do with product direction. And so, you know, we were walking all the way down.

Yelling at each other.

Full volume, stopped at a McDonald's, walked into McDonald's, grabbed some food, walked out, and resumed yelling at each other all the way down.

So there were a lot of moments like this. There was just high tension and, you know, strong personalities and strong thoughts about what should happen, like, work again, what will make the company better. I think that was really the conviction that I had and that he had. But the first thing I called him afterwards, you know, I think a week after I'd been CEO and people were doing the same to me. You know, I told them, wow, I'm sorry that I was such a pain. You know what? You know, it's like, it's a difficult job because you're. You're trying. You don't want to tell people, hey, like, this is what we gotta do. This is what I think we should do. You want to hear people out. You want to help them remain motivated to push things forward, that they should be pushing forward. And you have to hold the line when it is, no, this is. This is not your decision. This is my decision. And that's a really difficult thing to do when you have people that feel very passionately. So I think that. I think that was the main difference was when you are the person who's the ultimate decider, you know, you can't just ram it all the way through. So, you know, that would certainly make life easy. But then you don't have to deal with the consequences of that. You have to deal with everybody that has opinions on what needs to happen.

This has come up in a number of conversations, and I've had this experience myself where people work at a company, they have this situation with their CEO, then they leave and they start a company and then they call the former CEO and apologize because they now realize.

That situation that they, when they're, when they're working for you and they're saying no, this is the right way and we have to do this, they, they don't appreciate the other aspects that you're having to take into account and the dynamic with that investor and then the round that's going to come up and then the person that promise it to with the customer and then the, and it's interesting because so many people, I think, especially at tech companies, I think a lot of people probably think to themselves, I want to be the CEO, I could be the, you know, one day I'll be. And then when you actually get there, they're like this, I don't want, yeah, be here.

Yeah, it's a special kind of thing and it's a special kind of pressure and responsibility and, and, and, and yeah, you've got to, you've got to have different ways of getting things done sometimes that involve a lot of, a lot of big opinions.

Yeah. Your product has evolved from what I've gathered and read, your product has evolved a lot from when you first started the company. Can you just maybe give us the story arc of where it started and where it is today?

Yeah. The question that we've tried to answer has always been the same and the question is going back to when Brian and I worked at Stripe together on deploying machine learning for customer support.

Well, the real story is initially we asked how do you automate away all of customer support and how do you apply machine learning to customer support? Because we have these tools in our toolkit. And what we realized along the way was the wrong question, the right question was how do you scale great customer support? In the early days of Stripe, Patrick and John Collison, the co founders, they, you know, they were doing support themselves. They would have the whole company over to their apartment to do customer support. So they deeply cared about it. But as an 800 person company, as a multi thousand person company with many different products.

You know, it's a different type of beast. And so I think every single company we work with has gone from that point of co founders of the empowerment or everybody deeply caring about customer support and how do you scale it? So when we started assemble, the question was that how do you scale great customer support? And more specifically going to support leaders.

And asking what I think should be called the product market fit question, which is Brian came up with this very particular wording. What is software that you need to buy where you hate your options? And so the need to buy part and the hate your options part kind of bakes in, well, yeah, there's going to be some software that you need to go replace. And for us, we heard about a space called workforce management, which was about the planning and the staffing and the resource allocation of customer support. This guy named Bob Van Winden, he ran early user operations support at Stripe and he had seen it evolve at Google and seen the problem kind of fall apart from about a thousand people in support to multiple thousands and the need for the software. So he told us about it. We set out and worked on it. Throughout the history of the company, we'd always been of the belief that new products should come bottoms up. Like the most, the most talented, the most motivated engineers and.

They just create things and sometimes you want to point them at the roadmap and sometimes look at the Google 10% time, sometimes you want to just let them try stuff. And so one of the tri stuff things that emerged was right after ChatGPT launched in November 2022, we had a hackathon and one of our early engineers named Jason Ma, he created this chatbot that showed up in Slack and it was answering questions for our own customer support. How do you set up the workday integration? And it was really surprisingly good. And so we asked ourselves this question, how do companies scale great customer support? It feels like we have a new answer to that question. It feels like the set of what's possible with LLMs and technology has changed pretty dramatically. And so Jason, you should definitely go work on this project and even more than that, we'll spin off a separate team to work with you. And it was called the new products team. And they were in a separate Slack, they were in a separate room of the office.

And you know all the kind of classic, you're going to play by different rules and build a new startup within this existing startup. But it worked out because both they were able to run. But we had this kind of coherent thread between all the products that emerged. It wasn't we're just going to go do AI to do AI because it's cool and we're going to automate away people. It was because that was a legitimate answer to the question, how do you scale great customer support?

I want the new products team part.

Can you walk through a little bit more? Like how many people on the different team? At least for what I'm seeing in companies, it feels like the only way for companies that have an established product and customer base and revenue and everything and everyone's talking about we got to embed AI. You got at least if the ones I've seen, the only ones I've seen be successful. Did what you just said. Can you just talk through that maybe a little bit more in detail?

Yeah, I think.

The, the way that we set it up and I wish we had a full pizza box team. It was a four person team, so half a pizza box. I think if we had more people in the company with spirit than I would run a full pizza box team. But we actually, we didn't draft people in because we had learned that the hard way where previously we had tried to create a new product. So this was actually not our first rodeo. We had just to give a little bit of context there and it ended up as a very powerful feature. It was kind of a differentiating feature for us in the enterprise. But we had built this, what we thought might be a new product around managing BPOs outsourcers and that had been super top down. Like we had this intern with an MBA who's very talented. She's at OpenAI now, but she built out the strategy around, okay, here's why this is a super compelling potential product and here are the people we should draft into the team. And it took us three, six months to get it off the ground. So we said we're not going to do that again. The strategy is we don't care. We're going to run through Y Combinator the just the same plan. We're going to do 12 weeks hard sprint. We're going to do a demo day at the end and we're going to see who wants to do it and we'll send out applications, we'll see in the company, you know, who wants to join this team and you know, roughly the target is, you know, two or three engineers and one go to market person, keep it balanced but you know, will depend on who, who, who's interested in. So I think the questions the application.

Were.

Why would you possibly want to do this? What have you done at assemble to date and you know, what's your experience with slash understanding of AI? And this was 2022, so it was.

Not quite the same as it is today where you have people clearly a ton of experience. You had to kind of really pull on the thread. So we had a lot of interest. We kind of picked together the team that we thought would work well Together. And then I think literally the most important thing was that we were running through. We didn't reinvent Y Combinator. It was just. We just take their playback and just try to do it in this room in the separate slack. I think 12 weeks is a pretty short amount of time. And so in truth, it wasn't like the demo day. Oh, great. Companies all in. This is a big pillar of our product strategy going forward. It took a little bit more time than that. There was another demo day three months later than that. There was another demo day three months later than that. And when it seemed like it was maybe working and we needed to put more resources into it in both engineering.

And go to market, that started to be a discussion that happened at the board level and throughout our executive team. Just how are we going to move around the pieces? But. But yeah, it did start with just a very particular.

Don'T reinvent the wheel, do the YC thing. But just within.

I really. The thing about people applying to work on is a good idea because I think when you do, when you do these things, a lot of people are going to be excited to work on the new shiny thing. And a lot of those people maybe aren't even good at their existing job, if we're being honest, you know, in some cases. And they're like, hey, I'll do something new, like put me on that. And. But also drafting people also may not be the right strategy because then maybe they don't give a shit on that, that thing. And I like the application. So who did the demo day? Was that just a one person?

It was a four person. It was, it ended up as a four person team. So it was. It was two engineers, one. And she had been our second business hire. So business generalist was her title and you can see why she was a good fit for that theme. And then it was my brother John, like our CTO. It was the four of them.

Pretty cool.

So you mentioned the LLMs. You mentioned what's happened. A lot has changed, obviously for all of us, a lot has changed. But you've really been, it feels to me in the middle of this change and this shift. And.

How do you stay. How does the product strategy stay on top of all these changes that are occurring? Because it does feel like things are happening every day. There's new products every day, there's new competitors every day. How do you stay on top of that? How do you deal with that? Do you. A big question I have is how much are you looking outward and how much are you looking inward when it comes to that.

Yeah, it's super tough. And especially with AI for customer support where we're competing with a new startup every single week. I mean truly every single week I hear about a new AI native automation, chat agent, voice agent, copilot, agent, whatever, right. And they're raising big rounds so it's really competitive.

For us. And maybe this is the benefit of being a company where this is not our first rodeo.

You know, I used to think mission was bullshit. I used to think the tagline, you know, why are we doing this? Is bullshit. At stripe it was we're going to increase the GDP of the Internet. And I remember when I was an engineer thinking that's what does that even mean? Right? But, but over time you see there's a difference between where a payments company just trying to grow more ARR and you know, live up to really high valuations, yada yada to we're going to grow the GDP of the Internet. A lot of the things that they do that you, you know, stablecoins, risk products, banking products, they've got a press. It's like we're trying to grow the GDP of the Internet here. So for assemble that it really is, we're trying to help companies scale great customer support. We've all been there as consumers. Customer support is not amazing most of the time. And it's not about AI. Like you talk to an AI and you use these tools, sometimes you just want to get to a person and.

Sometimes a person is helpful because they're empathetic. Sometimes a person is helpful because they're not going to just follow the policy that's in the book. You can tell, hey, this matters and I'm going to make a difference here if I just tweak the policy a little bit.

Sometimes it's a person because they know how to work the system just like that, Right. But for various reasons you want to have this as a consumer ability to just get your problem solved. And then when you look inside of the company, then what we tell people today is you want a holistic strategy. You want AI to automate certain things. You want AI to augment your people to make them more productive, to help them ramp faster. And you still want people and you're still going to have big teams and coordination and resource allocation is a problem. So you want to make sure that your customers get to an AI agent or a human agent or something in between right away. And so the way that we've tried to keep up, tried to.

Stand out in this pretty crowded field is to both look inwards and outwards. The inwards part is to stay true to what it is that we're doing. We're trying to help companies scale, great customer support, full stop. How we do that is just different types of answers to what we think will be most effective. And then when you look out, it's to say, yeah, these AI companies, AI native companies, they work a different way, they use a different tech stack, they're taking advantage of different types of go to market tactics and we have to learn from that and adopt it really quickly because they are moving really quickly. So it's a bit of both.

Do you.

The moat. I, I look at all the, the, the speed not just in your space. Every, literally every market is just flooded now. Flooded with new companies, new everything. I've been thinking a lot myself about what is the moat in today's world because it is hard to make the product the moat. I mean when it's the speed at which people are developing and, and everything else. The mission as moat is a real, that is a real thing. Purpose as moat. Because people approach their jobs. I, I think people approach their jobs comp. Customers.

Are drawn to those missions in a different way as well. I think execution as moat. I think there's all this Moat brand which I was truly never a believer in, I think is now becoming moat because over time the other things maybe data, I mean probably data on the product side because most of these AI companies have no. If you're a new company, you have no data by definition. I, I assume so. I think all of that.

Do you feel that. I guess what I'm, I'm asking is I'm not in the trenches right now, you know, in that battle, but do you feel these kind of different kinds of moat in your business?

For sure. And I think when they all line up to the same thing, when they overlap with each other, the value of that compounds. So what I mean by that is mission is mode for sure. We talk to so many people who are really talented engineers and increasingly you hear it more and more over the last several months when people think maybe AI is a little bit overhyped and.

Maybe the implications of we're going to get rid of all jobs, like that's not something I really want to do, you know, that's not something I believe in. And, and, and people tell us, you know, this view where we want AI and humans to work well together and customer support that really resonates. We want to build copilot tools that make people better. And over 50% of our users are outside the US so they really resonate with that as well, the audience. And then when we go to customers, I think part of the product mode and the, the pitch there is not just getting AI, you're getting a holistic strategy. Because maybe your C suite still believes, or maybe your investors don't believe you want to cut all of customer support. I think that was maybe true six months a year ago, but that's not really true today. You know, people are saying, whoa, okay, you know, maybe we, there was a famous company in our space called Klarna. So we got rid of all of customer support and we're going to. Or they had gotten rid of 700 people, get rid of all of it. And it was just way worse. The quality was bad, the response times were worse. You know, they were sending out bad answers. So now they're trying to hire back. And I just think there's a much more thoughtful approach from our customers and that very much ties to the same story we're telling in terms of the mission mode. Hey, we understand customer support, we deeply understand customer support and that's why we've come to this approach and people resonate with that on the consumer side, on the customer side. So I do think these things stack together and then we start to think about more tactically or more strategic like product strategy or go to market strategy. We've got data in our workforce management platform that is really helpful to make your AI agent better. If you are. One of our customers is Honeylove and they're an E commerce company and they're pretty sophisticated automation.

Damn frustrated customers that come in and say, I want to get to a person. And so with the data we can reach in and say, oh yeah, there's somebody available, somebody who's a billing expert. Are we going to get you to them right away? Or we can say, you know what? Actually, no, there's, it's going to be a 15 minute wait. Everybody's tied up, or we didn't staff properly today. So you could say, you know, have the AI, try harder. You can tell the person like, hey, nobody's available. Are you sure you want to go to a person or you want to keep working with me? But you can design these customer experiences now that are more end to end because you have the data. And again, that, that ties to the philosophy that we have. It's human and AI, not just AI that ties to what customers want from us in terms of what they're the way that they're designing their operation and so all these things stack together in terms of model.

What is the biggest challenge you faced since starting assembled and how have you overcome that?

I, I think it is this moment of, of, of adapting to AI And.

I think I remember so Emergence Capital was one of our investors, they were early investors in a company called Viva. Most people don't know about Viva. It's a huge, it's one of the biggest staff companies out there. And there's this guy named Peter Gassner who I had the very lucky chance to pick his brain a little bit right as the ZIRP window was closing, I think this was.

Beginning middle of 2022. And.

We got on the topic of building multiple products, building a second product. And he told me that they intentionally went multi product early on and had the second product as far away from the first one as humanly possible. Because the belief was that everything else in between would kind of fill itself in. Natural gravity is for you to be a little bit more derivative, right? Like I'm gonna so pull this product roadmap like this. And then he said, we almost broke the company. Culturally, these two things could not exist together. And I think the challenge which I, which I hadn't appreciated, I just thought break the company in terms of trying to do too many things. But it turns out breaking the company in terms of culture is a very real thing. We had, you know, as our AI products were starting to get successful, we had people who were playing by different roles and people who are over here like, what the hell? How come they're having so much fun, right? Or in the reverse, you know, we had this group who was saying, you know, it's us against the rest of the company. Because if, if we're not successful enough at this next demo day, our project is going to get shut down and everything we worked on won't matter.

And then when you're reattaching sales, our first product was classic SaaS. Second products usage based, different types of motions, not just even terms of like the technical, but just the, the pricing mechanics.

And you have to learn a new thing. And you know, the innovator's dilemma is real. You have to learn a new thing when you're doing pretty well on your first thing. So you know, why, why are you going to put the effort in to do this new thing when you're, when you still have your old thing? So all of the challenges around, we had a kind of successful where you could see this kind of trajectory, new products and you're trying to attach it into an existing product and tell people the story as you're figuring it all at the same time. All of these turned into huge festering cultural problems where.

Like Peter Gastner said, we almost broke the company.

Having again been through some of these things before.

This, this actually is great. Full circle back to the conversation about being the CEO and having to make these decisions that other people can't necessarily see or understand for the long term, but in the short term, the pain that it causes people. People get frustrated. You know, I had a situation like this, did the same thing, roadmap. I didn't even think about it that way, but stretch the roadmap and everyone except for one salesperson, the entire go to market team quit over a period of 18 months because they also, what the hell are we do? What are we doing? And I was very angry at the time. And when I reflected on, I said, I can't really blame them because if I were them, I'd be confused, I'd be frustrated, I'd, you know, and. But to get to the next stage of the company. If I didn't do that, we'd be out of business for sure.

That's such a hard thing. I think we got lucky because before everybody on sales quit, we had tried this thing where.

We tried to open up the new product to everybody and that failed disastrously. We said, hey, we really want you to sell AI products because AI is the future. And it didn't really stick and, and people were really frustrated and we got lucky that our, our currently bestseller. This guy's having an amazing, amazing, amazing year. Like 300, 400% or something. But this time last year he was having a real done year. I think Ryan's on the board.

It was pretty easy to, to go to him and say, hey, Brian, you know, like, seems like things aren't really worth.

Do you want to be, you know, the dedicated seller on this new product that nobody wants to know.

That nobody wants to sell?

But of course I get, yeah, yeah.

It'S the right moment for him and he really leaned in. We got very lucky on that front.

Where is assembled in three years, it's 2028, you know, look out, almost end of 2028. What is, what does the company look like?

Yeah. I think what really gets me excited is not just customer support. You know, I mentioned that we, we want to help companies scale. Great customer support. That's the question we're about to answer. And you can see pretty clearly how the combination of AI for automation for augmentation and for operations as well. How? That's going to have a pretty good answer to that question.

I've always thought about this, this, this other question, which is the last flight that I took into New York I think was delayed four hours. You know, we went out, you know, under the, to the Runway and you could hear something was weird, like the engine was weird. And then you just kind of sat there and they were running through their checks. And then, yeah, there's some operational challenges and we're going to go back to the gate. And then we went back to the gate and people came on and anyway, it was painful. It was really painful. And I think about just 120 years ago now, over 100, it was early 1900s. Flight was invented. And you know, that must have felt very magical. Probably just as if not more magical than, you know, the first time you use ChatGPT. Oh, wow, that's pretty, that's pretty good. And yet our day to day experience with flight is just absolutely horrible. And you can see all these little things, like all the things around. Flying itself is pretty straightforward. It's still pretty magical. But to get to the airport, to get through the security, to all this stuff before you get into the air, all the stuff after you get out of the air, that's the painful part. And I think customer support is one of those problems that comes after the big idea. After your product goes to market, after your technology goes to billions and billions of people in operations. Just like with flight, just like with healthcare, just like with manufacturing, there are a lot of other functions that rhyme with support, where it's the operation, the operations that come after the big idea. So I think assemble would start solving some of those things. Taking the primitives in terms of staffing, planning.

In terms of negotiating. What is the difference between what AI and humans are handling, in terms of simplifying some of the workflows and automating parts, a way that should be automated and then augmenting where they should be augmented. We'll take it outside of customer support and use support as the blueprint.

Cool.

I want to transition to your background. Where are you from originally?

I'm from Chicago, so the Midwest. Everything we talk about as far as the company, the values and even these operational challenges we talk about, I think come from being Chicago. It's a very Chicago thing.

Did you, I mean, you and your brother, were you always very close? Even at like a young age?

I would say I would not have predicted that we'd be working this closely. Together.

And.

You know, some people are close in that they're good friends, and some people are close in that, you know, they're a little competitive with each other. And I've, I've definitely had people assemble, asked. And this is something you have to be careful about too. When you work with a family member or siblings, is that how you talk to your brother?

For our whole lives.

You were close for the kind of a competitive way early on.

Was there something in your upbringing, entrepreneurial, something with your parents, something with family, something that you were exposed to that put you down this path? Or did you just come out of the Stripe experience? Where did the entrepreneurial spirit come from?

Yeah, I, I think I'm not like most people who, who start companies in that. I thought I would be a professor. I thought I was going to be, you know, an economics or a statistics professor. And.

I worked for this guy Steve Levitt, like at his, he had a consulting company and he was the co author of Freakonomics. And I just have this very kind of like deeply burned into my memory, going to his office and ask him, hey, Steve, I think I want to be, you know, I want to apply to grad school and being an economics professor. And he asked me, do you want to do that? And, you know, I give this really, you know, what I thought at the time was a genuine response and said, I don't think you really want to be a professor.

So, so, so, so not. Because I think it was always, you know, burned into my brain like, okay, we're gonna, I'm gonna go start a company. But, but I think if I, you know, piece together some of the things, it kind of emerged over time. Like, I really, I went to this really kooky school called the Illinois Math and Science Academy. And it's a, it's a public boarding math and science school.

Public boarding I don't think I've ever heard of.

There's very few of them in the US from a, from like the late 80s, early 90s. It's, it's, it's really a special thing because I think, yeah, going to a boarding magnet school when you're 15 or something, it really forces you to kind of learn for your own. And I think a lot of, a lot of the skills that I have today I owe to that experience. And then certainly at Stripe, you know, amazing place. My, my recruiter was Danielle Amade, who is now president and co founder of Anthropic, you know, week one. Greg Brockman, the CTO of stripe @ the time, like ran the onboarding and vice president of OpenDam. You know, when you're kind of in that, when you're in that talent density and in that pool and, and, you know, I think part of it was, yeah, I, I think, you know, these people are really smart. I want to learn from them and be, you know, I keep up with them and, and also I can do the same types of things. They can. I think that was one piece of it too. Just seeing it happen at Stripe and seeing, and being part of it and kind of being inspired to say that, oh, yeah, I can do that too. And then I think the last thing, just being the problem tied to it, like, it just, it just kind of happened. Well, yeah, the thing I'm working on feels like it could be a.

Company.

What.

The thing about being inside of Stripe and seeing that and, and I'm assuming I, I. There must be so many Stripe alums that have started companies. And I think that's a big thing because when you don't see people doing it, you may have that idea, but not think it's possible to go do it. But when you're around it all the time and you see everyone else doing, you say, yeah, I have an idea. Why don't I go do it? It's one of the things I've learned in these, in these conversations is people who are the founders usually had somebody, it could be anybody, somebody that they saw start something, build something, could be their parents, could be their co workers, something that made them see, oh, it is possible. Because if you don't see it's possible.

Making the leap is pretty scary and hard. If you don't see that it's possible. I can, I've never been in a company like Stripe or Google. I can only imagine what that.

Energy is, is.

Like. You definitely, you definitely. You know the truism put yourself around great people and you'll be the average of, you know, the six people that you spend the most time with. That's been very much true in my.

Experience. What is it that drives you, that motivates you kind of deep at your core? Why, why do you want to be.

Successful? I think at this point in time, like, I've been, I've been very lucky and like I said, I could have imagined being a professor. And so I feel really quite lucky to have been on the trajectory that I've been on and been in the places that I've been.

And for me now, it really is this kind of feeling that.

People aren't paying attention to Something in the world, nothing being technology pointed at the boring operational problems. And so it really is this idea that within customer support and more broadly.

Just somebody's got to go fix that. And we're the ones to go fix that in terms of making customer support scale better, in terms of taking those learnings and applying them elsewhere with flight logistics. Because absent that, we're just going to have the same cruddy stuff for a really, really long time. And the world's best people are going to be doing the shiny new thing, which is amazing and awesome and important, but nobody's paying attention over.

Here.

If you go back, Last question. If you go back knowing everything you know today and all the experiences you've had, if you go back and give yourself one piece of advice before you started your first job ever, what would that piece of advice.

Be? I think it would be to, to, to go be more open and to go seek out people. I, I think in, I went to the University of Chicago and it's where fun goes to die. And I enjoyed that. And you know, part of where fun goes to die is that you, you know, because you're in the library or, you know, you're working on your eighth problem set for the week. But, but then you leave and you look around and start all the people who are in these classes, who you spend time with together, the, you know, it's the, the trope that it's, you don't go to school for the school, you go to school for who you're exposed to. And they're really interesting, amazing people. And I probably AM Close to 20% of the people that today I would say, oh man, I, I, I would have spent more time with them picking their brain trading ideas. So I, I think that's the advice that I would give myself is just be a little bit more open and seek people.

Out. Great advice. First person who said that and it's, it's great advice. Ryan, thank you so much for doing this with me. I really enjoyed this, this conversation. I learned from this. So thank you for doing.

This. Yeah, thank.

You. Awesome. Awesome. Well, I hope everyone enjoyed listening. If you did, please share this out with your networks and we'll see you for the next episode of Not Another CEO Podcast. That's a wrap for this week's episode of Not Another CEO Podcast. Thanks for joining. For show notes and more, please Visit not another CEOPodcast. Com. We'll see you next week.