Inside Deel's $1M → $1.5B Sales Machine | Chris Lee

0:00You scaled Deal as one of the first sales hires from$1 million to$1.5 billion.

0:07Chris Lee: First year at Deal, we went from$1 million to, I think we ended the year at$50 million. The next year was$50 million to$300 million. And within four years, we hit$1 billion in revenue. We were rated as the fastest growing software company in history. This was pre-AI. It was quite crazy. Chris Lee, head of sales Americas at Deal. She had, I believe, zero attrition of director-level sales leaders in five and a half years. How? We could onboard them in two months, not nine. Speed can be a reason why people buy. Deal can be a trillion-dollar company. I know it's controversial, but I'll tell you why.

0:57Chris, welcome to GTM Now.

1:00Chris Lee: Thank you. Honored to be here. Honored also. Super excited. Like you said, GTM Now exclusive. We'll take it. But, you know, you scaled Deal as one of the first sales hires from$1 million to$1.5 billion, which is just tremendous growth. And so take us back through that journey, through all the pivotal moments. And let's start with the very first one, which was what was going through your mind when you joined Deal? Like what brought you to Deal? What did you see in this small startup before it obviously exploded? Yeah. So my background is this. I originally joined my first startup was this company called Granular.

1:43Chris Lee: It was another Andreessen Horowitz company. they did something unique, which was software for farmers, mainly financial software. A lot of farmers spend their time in spreadsheets, managing multi-million dollar businesses in spreadsheets. And there was an opportunity that I was looking into. Like, for example, what was the next frontier that software was going to disrupt? And you had companies at that time, This was like 2014, 15. Like Procore, if you heard of them, they were disrupting the construction industry. And they had become a billion-dollar company off of construction tech. And I was going down the list of what other industries are left that are left to be disrupted because I didn't grow up on a farm.

2:35Chris Lee: And agriculture came up. And so that's what attracted me to this company. I was attracted to the challenge of here's this industry that's kind of old school, but it's bound to get disrupted by technology. And Andreessen had invested in this strong executive team and a tech company called Granular to go disrupt them. Ultimately, we ended up growing that company. I joined as employee number 11 pre-revenue. We grew that company$35 million in revenue. We got acquired for$300 million. At the time, that was interesting. It was like it wasn't a grand slam. A grand slam was like a few billion in like 2017.

3:23Chris Lee: But$300 billion was interesting. And I worked for DuPont for a while. Now, how I found Deal, this is how I weave in the story. How I found Deal, as we were growing granular, I was leading the sales team in the U.S. And we were trying to expand into new markets. so another large agriculture market is in Australia a lot of farms in Australia and we had approached the market by just you know I was I was personally cold calling email outbounding farmers in Australia working crazy time zones and you know it doesn't scale I even got to the point where I'm going to move to Australia for like four or six months to go launch a team there.

4:13Chris Lee: Now, what went wrong with that? Because the company had never had experience going global. We didn't have experience doing it. Now the executives did. Maybe that was like a lacking thing at the time, but we were learning as we were going. And as I interviewed a bunch of people, I finally found the first few people that I wanted to hire. I go to make the offer and the HR team stops me and they say, hey, we can't hire this person. We are not ready to hire this person. We don't have the compliance. We don't have a business entity in Australia. There is no way to pay these people in Australia. Right.

4:55Chris Lee: And fast forward, that set the company back from launching internationally by about nine months. It took nine months to finally set up the business entity. And that always stuck with me because as a startup, you want to move fast and launch into new markets and find new revenue streams. And because of compliance and complexity international, we couldn't do it. So fast forward, I worked for DuPont for a few years who acquired Granular. I end up launching my own company. Terrible idea. Not many people know this. But in January, I've always wanted to start a business, right? Right. And I learned a lot from this.

5:40Chris Lee: But in January of 2020, I started a recruiting firm, a tech-enabled recruiting firm, right, where you leverage data. At the time, I didn't know. I couldn't have predicted what would happen. But what happened is every company stops hiring. Pandemic hits, shutdowns, you know, nobody's going into the office, freezing the hiring budgets. Nothing's happening. And I thought this is the world's worst time to start a recruiting company. And so I go about it for a few months. It's failing. I'm like, I see the writing on the wall. The pandemic's not getting any easier. And I just, hey, let's chalk it up to bad timing.

6:28Chris Lee: I also learned a lot in the process. I didn't think recruiting was the best business. I wouldn't do it again. Even the tech-enabled recruiters, you rely on LinkedIn. That's a side note. You rely on LinkedIn. LinkedIn, you can't scrape. I don't know. There's all sorts of problems with that. But I decided I'm going to pivot. I really want to get back into sales leadership. I want to find a company where I can invest the next 10 years at. And as I was looking across the landscape of companies that Andreessen has, I have this notepad of, sorry, an Evernote of companies that I wrote down at the time.

7:08Chris Lee: This is in 2020. And Deal was one of them. And I reached out to Alex and Schwo. And on. How did you reach out? On LinkedIn. LinkedIn. Multi-thread. You got to multi-dread. So I apply online. Now, here's the catch. Here's the funny part. There was not a head of sales role on the career page, but I knew I really wanted to join the company. And there was a head of sales APAC role on the career page. So I apply to that. I ping Alex and Shoah on LinkedIn. I send them an email. Hey, I just applied to this role. Would love to meet you and got into the interview process because I had experience launching Australia in my previous company.

7:54Chris Lee: I was willing to move to APAC if necessary. This is at the time. I didn't have a family or anything like that. Now, what was funny in the interview process after like eight interviews, they end up saying, hey, we like you, but we don't like you for the head of sales APAC role. We want you to lead our sales team in the U.S. I said, okay, even better. And I ended up joining the company. And the thing that resonated with me, because at the time, Deal had some early signs of success, but it wasn't apparent. It wasn't apparent it was going to be a rocket ship at the time. One million in revenue. They got some traction, a couple hundred customers.

8:39Chris Lee: It was mainly the founders selling and a few sales reps that they had just hired. But what attracted me was I resonated with the business problem that they are solving because had my previous company, Granular, had deal, they would have launched in Australia in two days, not nine months. And to me, it just resonated with me. I was like, that is pure value. I understand this. And if I understand it and if I know my previous company could have been a fit for this, I know there's other startups looking to expand globally who would be a fit. So I understood the problem. That's what attracted me. Which is such an important part.

9:21I think one of the most underrated parts everyone says is to really feel the pain and be passionate when you're selling it.

9:27Chris Lee: Yeah, that's right. And so you join at around a million ARR, mostly founder-led selling, like you said, maybe a couple sales hires or SDRs in the mix. But you're really building out sales in America. What were some of the key inflection points of that build and of your scale that has now led you to$1.5 billion in revenue? I learned a lesson in the first 30 days of joining. And this is from our CEO, Alex Bouaziz, who taught me this lesson. and so I come in with a lot of experience. At the time, I had managed a team of 50 sales reps roughly and I come in and I'm ready to make, I'm analyzing everything in the business and I'm ready to make changes.

10:13Chris Lee: I come up with a playbook, here are my thoughts, here's what I think is going wrong, here's what we're gonna do. Alex rips that apart and says, no. Within like the first week, you're going to go sell and that's what you're going to do. And you're going to learn from that process and then you're going to build this up from scratch. And that's a principle actually that I've instituted as part of our culture on the sales team. Every leader that we hire, you are going to spend your time the first 30 days taking inbound leads and selling. You're we launch new products, our directors, including myself, we're going to learn how to pitch those products.

10:59Chris Lee: We cannot be the types of leaders that are in our ivory tower making decisions without understanding what's happening on the ground. And so that was my first bit in the whole 1 million to 1.5 billion journey was, okay, I'm going to be in the trenches, I'm going to sell, and I'm going to learn from that process. And it was eye-opening as to what we could potentially build. That's a, I mean, super fantastic lesson and definitely a very important one now with AI and realizing that everybody is now a practitioner. And if we even take a step back and just zoom out a little bit, for anyone unfamiliar with Deal, which I feel like most people are, but just in case, would you mind giving just a quick summary on Deal before we continue?

11:44Chris Lee: Yeah, so Deal has evolved. And what we are today are a global HR, payroll, IT, and now AI platform. We have four verticals, okay? And what that means in terms of like what products people buy and what problems we solve, whether you're a U.S. company that is just looking to hire people and pay people and ensure that they get a laptop on time and in time for their start date, Deal is going to manage that entire process for you. But where we are really strong, where a differentiator is, is we also have built the infrastructure outside the U.S. So as you build abroad and you want to expand into new markets, Deal can help you.

12:34Chris Lee: It's a fully compliant HR payroll platform in pretty much any country, any non-sanctioned country. We can help you hire, pay, manage your employees. Perfect. Super, super helpful. Thank you. And very timely, like we were saying with the pandemic now and post-pandemic when people are running more distributed organizations, including yourself. You know, you're running a distributed sales org, I believe, at Deal. Before we jump back into some of the key lessons learned, just as you built out the organization, how have you been able to scale a team successfully remotely? What are some tips for anyone that's looking to scale a remote team?

13:14Chris Lee: Remote teams, yeah. I had never worked at a company remote. It was in office culture at my previous company. So the first time I'd worked remote was at deal. And I don't think I would change anything. Like I'm going to be working remote the rest of my career. I don't know if I ever want to go back into the office. And, you know, it's not all that different. If you work for a large company and you have one of these skyscrapers, like the Salesforce building, for example, if you work in the Salesforce building, you have colleagues that you work with on other floors. And as a sales rep, you're going to be in demos.

13:53Chris Lee: You find yourselves in one of those telephone booths or locked in an office on Zoom calls all day and even on internal meetings. So what's the difference really between going to the office, locking yourself in a room, joining Zoom calls versus being at home, being on Zoom calls? But you don't have that commute back in home, back to and from work. So you save time, you save money from doing that. And it's much more efficient as an individual if you can work from home where you have your setup. I have my multi, what do you call it? I have my two screens. I have my strong Wi-Fi. So that's the thing on remote work.

14:41Chris Lee: Second, how do you build a business around this? How do you scale a sales team around this? I actually think it's easier. I think I have an easier job to scale a sales team remote company than if it were a company just in San Francisco. Why? Why? Because I have access to a talent pool anywhere across the U.S. and Canada. I'm not just trying to hire in a 30-mile radius of the office. And that allows me to hire the best of the best talent regardless of where they're located. I do think that's a superpower for our company. Yeah. Rapport is something that people often bring up with remote organizations.

15:28But I think the reality is even when you are remote, you're still getting together every so often. You've typically got some off sites or typically got some other ways of building rapport. It's more of an evolution than simply in person where you might go for lunch.

15:41Chris Lee: Yeah. In terms of building rapport, there are some cool things that we do. We have an annual sales kickoff where it's always been international. So last year we went to Dubai. The year before we were in Spain. and it's always somewhere cool. And then we fly the global sales team out to that location for a week. So we have this annual kickoff. We do quarterly offsites. We have hubs of people where people work and they do a lot of stuff. They get WeWorks. They have WeWork days. They'll do dinners and whatnot. So that exists. And we're very Slack native. I'm always sending audio notes and things like this.

16:27Chris Lee: There are ways, videos, there are ways to bridge the gap, create rapport, establish relationships with people aside from being in person. Now, I will say because you don't see your colleagues in the office every single day, when you do meet in person, it is so special. um you uh there have been times where i've worked with someone for years and i've never met them in person and finally get to and it's like knowing a friend that you've never met um and you immediately just kick it off i don't think you experience that quite as much if you just see the same people in the office every day yeah you have to really be intentional about how time is allocated, whether it's work time or building report time when you're in office.

17:18But you're right. You get that cool surprise and delight. So you scale this organization globally. You've done that after that lesson in the first 30 days. What are the other lessons along the way or pivotal go-to-market and sales decisions that really has led to this outcome?

17:35Chris Lee: Yeah. So when you launch a company, you usually identify a specific problem that you're solving in the market. and it starts with one product and you're focused on a single segment. And so for us, it was a very transactional product. It was a SMB types of companies that we were selling into sometimes. I mean, Alex and Shwo were incredible at selling deals over the phone on the first call. So within the first 30 minutes, getting them to sign up. And obviously as you grow, Usually companies don't build billion dollar, hundred billion dollar businesses off of one product. You have to scale into multi-products.

18:21Chris Lee: You have to be a platform. You have to scale into different segments. What's crazy about deal is we achieve this scale when most companies take seven to ten years to get to the scale and level of maturity. And that is time that you earn where you have the time to adjust and build. And you have tenured talent who can build playbooks and process. We didn't have that luxury. You had to build this within one or two years at the same level of scale. And so it really was drinking from the fire hose in terms of how do you scale fast? and within the first year at Deal, we went from$1 million to I think we ended the year at$50 million.

19:11Chris Lee: The next year it was$50 million to$300 million and then it went from$300 to I think$500 or$600. And within four years, we hit a billion dollars in revenue and now what we've ended with, well, what's public today is$1.5 billion in revenue. I think the thing that put Deal on the map, what made the company noteworthy was in 2023, 2024, we were scaling so fast. And as a software company, we were rated as the fastest growing software company in history. This was pre-AI. This was super impressive pre-AI. Nowadays, we've been eclipsed by a few companies, Claude, for example, OpenAI, for example, and a few others that are just crushing it at an incredible pace.

20:06Chris Lee: But we still continue to move fast and we still hold that culture of moving fast as a business. And I've heard, actually maybe before that, you know, this is true with now a lot of AI companies, but an important note is many of them have a PLG motion, whereas deal scale predominantly, I believe, with sales-led motion, which feels like it should get its own throne from a sales motion perspective. Or B2C versus B2B. Yes, yes, precisely. Exactly. There's some key differences there. Yeah. And, you know, I would love to see a PLG motion. The thing is, we deal with complex products and companies come to us.

20:55Chris Lee: They are trying to understand how did they overhaul their existing systems? A lot of companies are using old school HR platforms, payroll platforms. They've pieced together 10 different products to actually make global HR and payroll and IT work for their business. So there's a lot to unpack there. We have over 20 different products today. But it's certainly a big feat to rip and replace a company's HRAS system. This is their source of truth. It's like a sales force for any sales leader. we're ripping and replacing the HR team CRM, essentially. But not only that, you know, what we're doing is consolidation deals.

21:41Chris Lee: This is the number one reason why we win right now is consolidation. Companies are looking to get rid of all these vendors that don't all talk to each other well and are old school and are not AI native. And they are looking to optimize that and consolidate that into one place. So that is a huge evolution in terms of our product, in terms of our sales team. To go from a very transactional sales process to a multi-product, go up market into mid-market and enterprise, you are selling a very complex product, not transactional. That in a lot of ways requires a different profile of talent. It requires enablement and training.

22:32Chris Lee: And again, we didn't have seven to 10 years to go through that evolution. We had one to two. It was quite crazy, but we've done it. And we're still improving. And deals obviously known for speed of growth, deal speed, if you will. What are some key insights of how to actually move fast? Because that's the speed that most companies, most founders are aspiring to do. So we have a few different company values. And for a lot of companies, you know, it's fluff. It's corporate jargon. I don't subscribe to a lot of company values. I'm not saying deals. But the one that resonates with me the most is deal speed.

23:15Chris Lee: And it's something that started when we were in our infancy. What deal speed means, it translates to everything that we do. You know, the decisions that we make, the processes that we build, and even the product. Speed can be a reason why companies buy. I'll give you an example. Coinbase, for example, one of our first enterprise customers. And when we approached Coinbase, they were looking at, you know, one of the legacy vendors who's known for payroll. Everybody knows this name. And they were looking to expand into Japan. And this company said it would take them nine months to expand into Japan, nine-month onboarding process.

24:02Chris Lee: They have a lengthy onboarding process. They move at a certain pace. And as a tech company for Coinbase, they're not moving at a tech company pace. So Deal approached them. And one of the primary reasons we won, because we didn't have the credibility. We were a company with just a couple years under our belt, just approaching enterprise. No enterprise company was using us. We didn't have any references. But the thing that won was the fact that we could onboard them in two months, not nine. And again, for a business who wants to expand into new markets, that's meaningful. So speed can be a reason why people buy.

24:46Chris Lee: And we often think about that in the product. How can we be the fastest company, the fastest product to onboard someone from start to finish? How can you be the fastest for when you fund your payroll to when the employees actually get paid? That can make a difference. So speed in the product is really important. Speed in decision-making, operating style, and culture is one of the things that set deal apart. I'll explain that too. Okay. One of my favorite operators is Frank Slootman. Do you know Frank? I don't know him personally, but I've heard great things about him from Chris Denion, who was the first sales hire at Snowflake and worked closely with him.

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26:56Chris Lee: So if you don't know Frank, this guy is a three-time CEO who's taken three companies public. And I can tell you that doesn't happen with luck. This guy is a machine and I think he's retired now. So, you know, you can't joined his next company. But his first company was this company called like Data something. I can't remember. It was in the 2000s. Then he was the CEO of ServiceNow. Then he was the CEO of Snowflake. And he wrote a book. It's called Amp It Up. And for the first time, I read a book where I 100 % resonated with this guy. I was like, yes, finally. It's not fluff. It's not corporate BS.

27:48Chris Lee: It's not someone who maybe was a leader 50 years ago and is finally writing a book. It's now. And these are fundamentals. And so I'm a huge believer in this book, Amped Up. But in the book, he talks about speed. And this is the thing that resonated with us the most. He talks about speed. He talks about – he put it in a way that I couldn't describe better. That's why I'm bringing it up. Yeah. He talks about speed as make your competitors' years your months. Make your competitors' months your weeks. Make your competitors' weeks your days. And, you know, speed and hustle and work ethic are reasons why companies win.

28:38Chris Lee: It's not just the right idea that wins. Because plenty of, by the way, plenty of companies have tried to do what Deal did. We were not the first company to have a unique product to go after this unique problem. There were plenty of companies. Within a few years, we dominated this place because of this cultural value called Deal Speed. and uh i actually um funny enough i reached out to frank slutman and uh yeah how did you reach out similar question as you'd expect linkedin multi-thread multi-thread beautiful i re i in fact we were selling snowflake and um i got the finance leader of snowflake to introduce me perfect Even better.

29:26Chris Lee: Yeah. And what attracted him, I explained to him, hey, I've read your book. I literally brought this book to our leadership offsite. We bought the book for everyone at the company. Our number one company value is deal speed. It really resonates with how you think about business. And we have a sales kickoff coming up, and I would love for you to do the opening speech. And although he didn't fly in, we did have him live remote to do the first five minutes opening speech in 2023 for our sales kickoff for the sales team. It was awesome. Very, very cool. It all comes full circle. It's incredible to see the impact that he's had through that book alone.

30:14Chris Lee: Yeah. And when you're moving at such speed, obviously you need to be hiring people. and you were hiring a lot of salespeople along the way, but you've actually had, I believe, zero attrition of director-level sales leaders in five and a half years. How? So I've had the honor of managing these 14 directors that I have today. I haven't had any voluntary or regrettable attrition at the director level and very few at the manager level as well over the last five and a half years. I'm not sure how long I can keep that record going. I mean, time will eventually catch up with us and somebody will leave.

30:58Chris Lee: But I think I've done a good job of hiring the right talent for the right role and who continually to uplevel the team. I think I've also made a lot of hiring mistakes. and I have a big principle when it comes to terminations. So some of those mistakes, I'll just explain, for example. Yeah. There have been people that come on our radar, that apply to our roles, that I get introduced to, who have an impeccable resume and who come from really noteworthy companies, right? and who, when doing back-channeling and getting references, have had celebrity CEOs put a reference for this person. And then I find myself thinking that they're not working out.

31:54Chris Lee: And when you've hired someone and you've made a mistake and it's something that you've overlooked in the hiring process, one of the biggest second mistakes that you can make is keeping them around too long. If you hire a bad leader who isn't a culture fit, who maybe doesn't have the right experience or mindset or skills for the job that they have, that's going to have a compounding effect on your business. Hiring is in terms of like a pyramid of what is most important for me, how I spend my time. Hiring is number one. If you hire the wrong leader, they're going to hire the wrong people under them who are probably going to hire the wrong people under them.

32:45Chris Lee: And it's going to take a long time to try to untangle that mess. And in a lot of cases, and I've seen it, it can set a company or a department back a year or a couple years to try to backtrack and get this back on the right track. And for a company that's moving as fast as deal, you don't have the time for that. You don't have the time for that. You have crazy goals to hit. So I have this principle where for the directors that I've hired, they've been with me for years and we have this super strong bond and relationship. And for the directors that are no longer with us, I have let go. And they were let go within a few months.

33:26Chris Lee: So hire slow, fire fast is basically the principle. And I think that's better for us as a company, but also that individual if it's not working out. And was it the cultural element that didn't work out for people that may have the right resume and these celebrity CEOs endorsing them. What was the factor that made it not a fit? Because I'm sure a lot of founders and operators also are receiving and seeing this and they're trying to actually decipher who the right fit is. Culture can be a huge piece of it. It goes back to that story about, you know, in the first 30 days, you need to be in the trenches with the salespeople.

34:03Chris Lee: You need to understand the role of the sales rep. If it's an SDR leader I hire, I want you to make cold calls. You're going to do outbound. You're going to understand the role of the people on the ground, and that's going to help you best shape that business. If you don't do that, what do people do? They do surveys across the team when they join, like, oh, what do you think are the problems? They make judgments based on how the company does it versus how their previous company did it. That's a massive mistake. Like I've seen that a million times. Culturally, not every leader, especially the higher up you get, the more senior, they aren't willing to get in the trenches and do that.

34:51Chris Lee: And so that was a big thing. Second thing that I think is really underrated is critical thinking. Critical thinking skills. Common sense, actually. so so how do you how do you suss out some of this stuff let's say critical thinking whether you're a leader that you're interviewing for or a sales rep your first sales hire that you're interviewing for one controversial take that i have in the interview process that a lot of leaders have been uh doctrinated indoctrinated with is i don't know what they call it i think it's like star or something interviewing, interview questions, something like that, where it goes like this.

35:36Chris Lee: They're behavioral-based interview questions. Tell me about a time. And tell me, so it'll go like, tell me about a time where you faced a challenge and you overcame it. And first of all, I would be offended if somebody asked me this in an interview. I would actually probably hang up on the interview. But it's actually the majority of leaders, they use these behavioral questions, tell me about a time. And I actually think it doesn't optimize for the right thing. It optimizes for who's the best liar, who can on the spot tell me a story of how they faced a challenge and overcame it. And there's probably a skill in that too.

36:23Chris Lee: I'm not going to deny that. Storytelling. But instead, I like to ask a scenario question instead. And I will lay out the scenario. And it's a scenario that every sales rep or every leader has ran into. And I will want them to talk me through it. If they are in this scenario and they're stuck at this pivotal point, what are they going to do? How do they handle that? How do they think about this problem? And we'll just chop it up back and forth on, okay, well, what about this? Well, what about that? Okay, well, you think that this is going to happen, but what if this actually happens? Because sales is unpredictable.

37:13Chris Lee: And I think you get a better sense of how people think. Again, it goes back to critical thinking, not who can make up the best story. And that has been effective for sussing out great sales reps and sales leaders. That's a great tactic and one that I'm sure a lot of people now employ. And speaking of a star methodology that you mentioned, I believe you also have some star methodologies for your actual sales process. You know, what is a three star versus a five star sales process? Tell us a little bit about that. That's a good segue. Yeah. So there's this topic that I haven't really talked about publicly.

37:54Chris Lee: And it's funny because people ask me about this in panels and conferences and whatnot. And the thing I say is, look, if we're doing something unique, the last thing I want to do is tell hundreds of thousands of people what we're doing. because sales is one of these things where people, sales and marketing, they quickly iterate. They're always looking for the new thing and they're copying, you know, what's working from others. I can tell you this. So there's a whole story about how do you operate a five-star sales experience? You've heard of customer experience. I'm talking about sales experience.

38:35Chris Lee: Nobody really talks about this. And where I got inspiration for this is, well, everybody stayed at a three-star hotel, like a Marriott or whatever. Maybe that's a four-star. I don't know. Everybody stayed at those types of hotels. And what is that experience like? You travel hours to your destination. You finally arrive. You have to wait 20 minutes in line to check in at the hotel. They finally give you the hotel room. You go up to your room, you unpack, et cetera. It's actually, you know what you're getting, but it's not, there's no wow factor in a three-star hotel experience. Now, for the audience, if you've never stayed, I try to say this without sounding pretentious, but one time I was at a wedding.

39:25Chris Lee: We stayed at a five-star, like ultra luxury hotel. Let me tell you the experience. You drive up, there's a gate to even get to the hotel. they know who you are they know what time you're you're going to arrive um you check in with the security you drive up to the lobby people are waiting for you to open the car door and greet you hello mr lee welcome to x you've already prepaid up front for your room you've already given them your ID and credit card through a portal. And there is no waiting line. Here's your key card. Let me take your bags. Let's go up to your room. There's chocolates on the pillow.

40:13Chris Lee: There's a concierge who's asked you, hey, what are your plans for the week? Do you plan to have dinner tonight? Let me book a reservation for you. It's quite a different experience at a five-star hotel. And I try to think about that framework in the sales team and in the sales process. When a lead comes in and they're interested in deal, what is that experience like? And the only way you do this, because I don't want to give away too much, is you map out your entire sales process today, end to end. And you think to yourself, what is a four-star sales experience? If today is a three, if today is mediocre, what is a five-star?

41:06Chris Lee: And you can even take this to the extreme of like, what is a 10-star if just for the hell of it? Make your own scale. Yeah. And you decide what are the things that make sense for your business to invest in? You know, there are things you can bridge the gap on to create a really personalized experience with your clients, with AI, that you couldn't do before. There are things that cost money. There's things that don't. And you can decide at every step of the journey what that experience can look like based on your product and your persona and your industry. So you have to think about the experience that you're giving your clients when they come in through the door.

41:54Chris Lee: And as an example, are they coming in on a weekday or a weekend? Maybe it's a founder who wants to meet with you on the weekend. Are you available? Five-star hotel would be available 24-7. Yeah. When a prospect does a demo of the product, does your senior leadership team get introduced to them saying, hey, I'm going to move mountains for you. I love your company. I've researched it. I'm super excited about potentially doing business for you. if there is anything that we can do, here's me, the head of sales, here's our director, here's the sales manager of the account executive that you're working with.

42:40Chris Lee: Here's my phone number. I've given my cell phone number to thousands of people at this point. You reach out anytime. And number one, all I ask from you is one, tell us about your experience. What do you like about deal, what you don't like, what could be improved in the sales process. And what I can promise to you is that we're going to move mountains to ensure that you're successful should you choose deal as your vendor of choice. And that simple thing has been incredible. I actually have a leaderboard, internal leaderboard. Most of the sales reps don't know this, but I have a leaderboard of responses from prospects, whether the sentiment is positive or negative about the sales process.

43:29Chris Lee: Because again, if you're a five-star hotel, you care about experience. You want to be delightful to the customers that come in. And I do think, although it's old school, one reason why people buy is because of the person who's selling them. Like, do they like that person? Are they proven to be a very competent professional that's going to help guide them through this evaluation that is not cheap and might be a headache for them? So this is something that we track. The five-star experience is something that we're mapping out. AI really unlocks this like never before. you can finally you know these are things that you would invest in for enterprise companies like if you had amazon come inbound or something like how are you going to treat amazon right are the founders going to reach out to the decision maker yeah um you can uh do things that were once important for enterprise same with account-based marketing why is it in the past that account-based marketing was limited to enterprise.

44:39Chris Lee: What is account-based marketing? It's basically personalizing the marketing and the content that a company sees. So when they're scrolling on Instagram or they download, they're surfacing a piece of content for them. It is personal. It might even have the company logo certainly customized to the persona, but it is personalized. Now, traditionally, that's always been done for enterprise because it's time-consuming for the marketing team. There's a lot of work required. AI disrupts that. Why can't you do account-based marketing for the S &P market, for anybody who comes through the door? Why? You got to show this five-star experience.

45:20Chris Lee: And that's what I'll leave it at. That's such a refreshing and important perspective because I think a lot of the time now with AI, people are excited to almost cut back that human experience as this part of the sales process. But you just mentioned key stakeholders are actually getting involved and things that are almost counter to that because at the end of the day, it is an experience. So very refreshing perspective. And now you're at$1.5 billion with Deal. What's next? Yeah. So here's a bit about the vision. Here's how I think about it. Deal can be, I know it's controversial, but Deal can be a trillion dollar company.

46:00Chris Lee: It's not that crazy, and I'll tell you why. Every company needs payroll. And there are, well, there's about$300 billion in market cap of public companies who do payroll and HR. There's a few hundred billion more of private companies who do payroll and HR. The most mature market is in the U.S. and what these companies have optimized for in their product is building HR and payroll for the U.S. market. Now, what's funny to me that everybody ignored, and one of the reasons why Deal was growing fast, is because the U.S. only represents 5 % of the world's population. You have 300 million people in the U.S., but it's much less in terms of like working class people who would be on payroll.

46:56Chris Lee: So if 5 % of the world's population is in the US, that means 95 % is outside. And the bigger market is if you can become the HR, payroll, IT, AI leader of the world, you should be a trillion dollar company. And certainly Deal is building the infrastructure to do that. I'll give you an example. of why infrastructure is so important. So an example. Yeah. You know, Amazon Prime. Of course. You order something if you're in the U.S., you order something and come same day, maybe a day later, most of the time. Right. Yeah. That didn't exist 10 years ago. Remember the days when you would order something and it would take a week, two weeks to arrive to your door.

47:54Chris Lee: That's because it relied on the infrastructure, the logistics infrastructure of UPS and FedEx. And over time, as Amazon grew, they knew they needed to control this. Goes back to experience. Goes back to speed as to why people buy. People love Amazon Prime because it's fast. Yeah. They would choose to buy from Amazon because they'll get it tomorrow and not a week from now. And so Amazon had this dilemma. Over time, they became the largest customer of FedEx. And during peak holidays, Amazon had to compete with other businesses who were also making deliveries to their customers. And they would have to rely on the infrastructure and the logistics of another company to ensure that their customers had a great experience.

48:43Chris Lee: And it's something that that they had no control over. And so what they started building was their own logistics infrastructure from the warehouses to the custom delivery vans that are optimized for the Amazon boxes. They make their own boxes too. And that is what enabled them to deliver Amazon Prime. And that has really changed the business. And that is a moat for Amazon. Nobody can deliver Amazon Prime speed today unless you're Prime. Nobody else has this infrastructure. Even the greats who focus on this, like FedEx and UPS, can't compete. And so that's how I think of infrastructure. And it's the picks and shovels.

49:37Chris Lee: It's the – if in our business of payroll, a lot of companies use third-party vendors. They use these old-school service-based vendors who are calculating payroll for you. They use a bunch of different systems. No one actually owns the payroll calculator. the math behind if this person with this visa and they're spending time in this country, in that country, how much should they be taxed? There is a payroll and a tax engine calculator behind all of that. And nobody really owns it. And so everybody uses the same few set of tools. And because of that, everyone's reliant on those vendors to deliver for us to be in control of our customer experience.

50:30Chris Lee: And in the spirit of deal speed, that's just not acceptable. So we started building our own infrastructure, building our own engines. To my knowledge, we are the company with the most engines globally. Define engines. Yes. So everybody knows of ADP in the U.S. ADP has a payroll engine in the U.S. We have built payroll engines in about 60 plus countries today. That's growing every quarter, including the U.S. So not just the U.S., but anywhere. And that ensures that this type of speed and experience when you're running payroll that you're used to in the U.S., which all the vendors have, you're going to get that in any country that you hire through deal.

51:25Incredible. Well, really appreciate you sharing that vision. Chris, you shared a lot about what has worked along the journey. What about what hasn't? Have there been any kind of near-death experiences or really challenging points throughout the scaling journey?

51:40Chris Lee: I wouldn't say we've had a near-death experience, but certainly it's not always been up and to the right. And I think one thing that I've learned and some experiences that I've never gone through before in my own career, as you grow larger as a business, none of the great companies that you think of that are public companies have a flawless track record in the media. And, you know, Now, one of the most attractive things to the media that will get the most clicks is not positive news, but it's negative news. And as you get larger, you're going to have people, competitors, who are going to try to cut you down.

52:29Chris Lee: They don't want you to grow so fast. So you rise above. You fight. You don't give up. You can cry, but only for a day. and you suck it up. I love it. I love it. And take me through or take us through a little bit more around your thinking in a different manner. You know, you just shared your thinking around these challenging times and how you actually communicate to the team. But what about more of, you know, the systems thinking of sales itself? Yeah. So systems thinking. over my career, I've gone through different inflections in my own learning, my own self-development. I always want to be a student in my career.

53:17Chris Lee: And where it started out was finance and investing. That's where I thought I was going to start a career. It's what I studied in college. I read every book on investing, every major book. I got into sales. I immediately started to read every sales book. This was before podcasts were popular. And it was an incredible experience because you know what? If someone writes a book, it means they are a true domain expert in something. If you're reading a book on negotiation or discovery, this is a person who has lived and studied this topic for years. And as a new salesperson in a role, you know, you have three options.

54:10Chris Lee: You can just do trial and error, which is actually the slowest. Yeah. You can hopefully, you can only hope that you learn from your mistakes because you have your own self-awareness to learn from your mistakes. Number two, you can learn from others or expect to learn from your manager, which is the wrong expectation and we can go into that too if you want. But this is also slow. Or you can try to consume as much information as possible. Nowadays, it's podcasts and eBooks and maybe TikToks on sales or something. But in my day, it was books on sales. And this is what had allowed me to level up so fast.

54:52Chris Lee: I'm a young guy. I have maybe 10 years younger than most heads of sales in my role. but this is what allowed me to scale up in my career so as my role in my career has has evolved over time I went from learning about sales to consuming every book I could on leadership and leadership and culture and how to drive a team to do things that you you have a mission how to drive them to accomplish that mission. And I've read every book there. I'm actually tapped out on books. And I've learned a lot from that process. And that's helped me grow as a leader. Where I'm at today with AI is, well, everyone goes through this mini evolution.

55:47Claude, OpenAI launches. Every CEO is like, how do we implement this into the business?

55:54Chris Lee: If you're not using AI, you're falling behind. Right. I spend countless hours. I actually like to think I wasted time. Not in a good way. I wasted time just fiddling with AI tools and building products internally that were subpar. and I kind of got to this point where you know so much of my career I have gone back to the basics let's be a student again let's go I learned about sales I learned about leadership what are the fundamental things what are the first principles of AI that I would need to learn if I'm an operator of the future and how I was reminded of this if you were to start a company today.

56:45Chris Lee: I wouldn't go hire a big sales team. The first thing I would do is optimize a AI-driven sales process. And if you want to go down that path, you need to be a systems thinker. And I don't like to outsource things. I don't want to outsource knowledge on what should be the future of how to build a business with AI to an operations team or rev ops or something like this who are systems thinkers who build systems and processes. So I went back to school and figuratively and started reading books on first principles, systems thinking, that sort of thing. and this is providing a really solid foundation for myself.

57:38Chris Lee: So when you think about your business, every department, this is not just a sales thing, but when you think about sales, there is a process. There is a system here. Again, leads come in, what happens? If this happens, then that happens, there's a huge set of branching trees and workflows that are essentially made up of your sales process. These things are made up of the talent that you hire, the incentives that you structure that ultimately dictate the behavior that your team drives, to the things like, you know, in order to get a deal done, you have to rely on some other departments like legal, like deal desk, if you're a larger company, um, like rev ops and, uh, onboarding.

58:35Chris Lee: So, um, there is a huge system here. And sometimes like, I wish, I really hope that I could someday get this. I haven't seen this doesn't exist, but I want to be able to visualize this kind of, I don't know. I bounce back and forth between different analogies. Maybe it's an engine. Maybe it's a watch with a bunch of gears. And with a really healthy go-to-market system, the watch is running perfectly. The watch is running on time. And if you have one gear in that watch that is broken or that is not working, that is not timed properly, it clogs up the rest of the system and it's not going to tell time on time.

59:21Chris Lee: And I would love to visualize that because, you know, as you think about your go-to-market process, if you have something that is a process or you have SLAs that delay other things that you want to accomplish, that might break the system. And you do have to be a systems thinker in order to unpack that in your business. The other thing that I think a lot about in terms of first principles is you have to break down a problem into its smallest constraints. And something, a framework that I give my team and they know, they already know. We've been working together, again, with my leaders for years together.

1:00:15Chris Lee: They know how I operate. So when they come to me with a problem, they already frame it in here's the situation, here's the problem, and here's my proposed solution. And instead of complaining, because I don't like complaints, they have to think about what is the problem, what are they trying to solve, why is that a problem. problem and I think you know first principles systems thinking whatever these are buzzwords but these are the things that go back to a leader who can be strong at critical thinking who can unpack problems rebuild them from first principles not just copy what they did at their last company but understand the situation at hand, what are the constraints, and optimize around that.

1:01:07Chris Lee: That's what we think a lot about. You know, on LinkedIn and on your careers page, there's a role live with the title Ghostbuster. Tell us what this means and whether other people should be hiring Ghostbusters. Yeah, I think so. Every, look, Ghostbuster, it's a real title. It's a real role. It's on our career page. They are paid handsomely. Who are they? They are people with experience in building AI workflows, probably consulting backgrounds, operations backgrounds, systems thinkers. And what do they do? So look, as you grow a company from 30 people when I joined to 7 ,000 people today, there becomes operational bloat.

1:02:02Chris Lee: And again, I mentioned our number one company value, it's deal speed. Over time, companies will grow and they get to scale and they start to slow down. And what can you do in order to ensure that you are developing decision-making operational power at a speed faster than you decay as you grow? This is what a Ghostbuster is optimized for. So as a company grows, it's unintentional, but companies start to slow down. Most companies do. They start to decay. And it's unintentional because, you know, as a startup, you start out as a generalist. Everybody does everything. You are in survival mode. You will do anything to get stuff done, right?

1:02:59Chris Lee: As you start to grow, you start to build processes. You have defined teams with defined SLAs. and if one thing used to take a day, all of a sudden there's actually multiple teams required in order to get this thing done. Each team has an SLA. They're all abiding by their SLAs. Nobody pays attention to when I want to do this thing. It actually goes through multiple teams. Each team is abiding by their SLAs. Each team is saying, I'm hitting my target. But for the customer, it's three or four days before they hear back. And that's a problem. This is where a ghostbuster comes in. They will analyze across the entire business the different processes that are in place and the speed at which it takes to actually get things done.

1:03:54Chris Lee: And oftentimes processes in the old world were manual. And now with AI, you can automate stuff. And as a big business, there is a whole lot that we need to go automate. And this is essentially what the Ghostbuster does. So whenever I have a problem, department agnostic, I can insert a Ghostbuster who will coordinate with all the different departments, who will understand from a first principles perspective, what is going on and suggest a new workflow or a new solution and then go out and do it. And they own the project end to end, which is difficult when it's multi-department problems. These are hairy.

1:04:42Chris Lee: Maybe my problem is not another department's number one problem. To have this third-party owner who owns it end to end and works with everybody has proven that even deal operating at a 7 ,000-person company, we have not slowed down. We have the same culture. We have the same startup mentality as we did as a 30-person startup versus a 7 ,000-person team. That is amazing. That is exactly what every company is trying to hold on to as they scale. Well, Chris, this has been fantastic. Really appreciate you joining us. All the insight that you've imparted on sales and the journey scaling deal. Where can people find you if they want to follow along with your journey?

1:05:25Yeah.

1:05:25Chris Lee: So on LinkedIn, it's LinkedIn.com slash techcontrarian, like technology, T-E-C-H. That is a fun fact. And on X, it's at techcontrarian. How did that start, that handle? I thought we were ending the podcast. I know. So, again, I wanted to be in finance in college. And I read a lot of books on Warren Buffett. he writes this book called The Intelligent Investor. Or no, Benjamin Graham, his teacher, wrote a book called The Intelligent Investor. Okay. And in there they talk about the contrarian investor, the person while people are selling, he's buying. And I've always thought about myself in the same way, the types of companies that I choose to work for, and the different decisions that we make as sometimes against the herd or contrarian.

1:06:27Chris Lee: And Chris Lee, at Chris Lee wasn't available, so I did at Tech Contrarian. Fair. That was my assumption. It may be a common name, but I love it. Tech Contrarian, for anyone looking, will be where to find Chris. Chris, thank you so much. Thank you.