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The Art & Science of Scaling a Sales Team

Career Journey to CRO

Barry: Let’s start off by telling a bit about who you are, Matt, and who you work for, and also how you got into high tech. The story you told me quite recently that I thoroughly enjoyed.

Matt:  Thanks so much for having me on the podcast. I’m currently the Chief Revenue Officer at Trulioo. We are an identity and business verification platform, working with companies all over the globe. How I got into tech, I grew up in the Bay Area in California, went to school at a small university in San Antonio, Texas called Trinity. And after graduating, I went and became a sixth-grade social studies teacher.

And at the same time, I had a couple of really good friends at Trinity who ended up forming Rackspace. There wasn’t a lot of tech going on in San Antonio, and so they were building this great company. And one of the founders, Pat, approached me when I was teaching. He said, “Matt, I really want you to come and join Rackspace,” and I thought, “What the heck am I going to do for you, Pat? I don’t know anything about technology. I’m a sixth-grade social studies teacher,” and he looks at me and he says, “Matt,” he’s like, “you’re selling kids every single day on why they need to go and learn social studies. You know sales. Come on over and work with your best friends and let’s go and build something great.” So I was able to go and join Rackspace and spent 10 amazing years there.

Barry: Love that. I really love that. I think this could also be a promo for getting people into high tech that were sixth-grade social studies. So that’s amazing. You also told me a bit about your career. I think it’s super interesting. Right now you’re the CRO of Trulioo, but beforehand, what got you to this position?

Matt: I’d say I got 10 great years at Rackspace, got a chance to have a lot of different sales leadership positions, had the opportunity to live in the UK, spent two and a half years there, spent a year in Hong Kong, running APAC sales. From there, I had the opportunity to do a turnaround at a company as CO at a very small pay-per-click SEO company. Then I moved to Austin, Texas, had the chance to go and run go-to-market for a company called Bazaarvoice right as they were approaching an IPO. I had a chance to go and spend a lot of time in Japan, Australia, and Brazil in that role.

And then, I was able to go from there to a company called WP Engine, which was a really fun six years of my life where I helped grow the sales organization from a single person. I started over there as the VP of Sales. I said, “Great, how many people are on my team,” and I heard the answer is one, and over the course of six years built that up to about 150 folks across the globe.

And then I took a CRO role at a company called Cosential, which was a CRM company. Spent about 18 months there when we sold it, and then was really blessed and fortunate to find Trulioo and have been there for about a year now.

Scaling a Sales Team in Early-Stage Companies

Barry Mueller: Cool. Love that. So a lot of sales experience, a lot of scaling experience going from one employee to 150 sales employees. I think it would be relevant then to discuss maybe scaling sales teams and scaling also the company. I want to differentiate between the two because the sales team is a siloed team, but now that you’re CRO you’re scaling a company as a whole, not just your sales team, but also making sure that the sales team is playing nice with some of the other teams or the other teams are playing nice with sales. 

So let’s start with the hiring process for scaling a sales team. What are the steps that you took when you had one sales rep? What were you guys focusing on then? And when you wanted to start hiring more sales reps, how many were you hiring and what did you need in order to get those hires onboard quickly in a good culture?

Matt: Yeah, great questions there. So first off, I start to go and try to go and build the model. And this is one of the things that I have seen time and again with early-stage companies with the sales team is they’re never quite sure when to go and start adding more additional sales reps. And a lot of times, maybe the sales team is performing pretty good, maybe not blowing it out of the water, and there’s a lot of thoughts like, “Well, how am I able to go and add more salespeople if my current team maybe isn’t averaging 110%? When’s that ‘right time’, and what percentage of the team do I look at before I start to go and add more people?”

And for me, the answer is really around getting into the inputs and not the outputs. Building a model, and every organization’s a little bit different, but you might have your SDR team and you’re looking at maybe some inbound leads, maybe some outbound leads, and you’re feeding that sales team some opportunities, maybe you’re asking them to go and do their own self prospecting, you got ABM campaigns and so forth. You start there and say, “Okay, let’s build a model that says we want to go and get each sales rep with X number of opportunities and average deal size of X. We’re looking for a conversion rate of this. Based on this average sales cycle, we want to go maybe there’s a channel player or whatever.” But you start with the model and then you hold people accountable to hitting that model, the conversion rate, the average yield size, and so forth. And then you can go and add enablement into certain areas where they might not be performing at a certain level. And then once you start to go and get that model, then it becomes really easy to be able to go and scale.

Sales Enablement That Focuses on Good Sales Behavior

Matt: One of the really interesting things that has happened now at three different companies that I’ve worked at, is sales teams performing okay, but once again, there’s this hesitation of, “Well, how do I add more people? What’s my current team going to say if I go and add more people?” You start digging into the model, and in three different cases the reason why the sales team wasn’t performing. There was a bit of a lack of enablement and a lack of really understanding the value propositions. But more than anything, they were forcing bad behaviors by the sales reps because they were actually over-feeding them opportunities. They had so many opportunities that they were forced to get really surface level with those opportunities, almost to the point of, “Let’s rush to a demo, and I’m not going to call you. Barry, if you’re interested, you can call me back, but I’m off to the next demo.” Of course then the performance wasn’t there.

And the industry actually in a couple of those companies was simply, “Let’s just add more people so actually people have less opportunities so they actually have more time to focus. Let’s make sure we have really good sales behavior, really good execution,” and the attainment went way up. So it’s really about understanding the model that you’re trying to go and do. Forget about the outputs. Figure out what the right inputs are, coach, and manage those inputs, and that will really start to go and help unlock when to go, scale, and when to add more people.

Barry: Right. I love that. It sounds like it’s the opposite of what most companies do. Most companies get numbers from their board that they promised either the board or the board told them to expect once they got the funding, and then they’re like, “Okay, how do we get those numbers?” And this is saying, “No, start from the beginning.” I would even say maybe when you even had one employee, start building what you expect from percentages, start putting in the numbers, see what your average contract value is, see how long it took to close, and then when you add more people, ensure that those numbers are consistent. If they’re not consistent, then you have enablement fill in those gaps. But you’re starting from the inputs, not the outputs.

Matt: Absolutely. And when you do that, then you avoid the possibility of having somebody that is underperforming. If you’re only looking at the output, what do you tell that person? “Hey, I need you to work a little bit harder, really need you to dig in. I really need you to go and lean in. I need 110% this quarter.” What’s a rep supposed to do with that? Quite frankly, it’s BS. But if you go into those inputs and you say, “Hey, here’s where I’m seeing the inflection point. Your conversion rate on outbound SDR-generated opportunities is half what it is for the other team, so this is where we really need to go and focus. Let’s get best practices from the other team members. Let’s learn what they’re doing, and so we can go and alter those steps.”

Understanding What’s Driving Good Sales Behaviors

Matt: For your top performers, you’re actually being able to go and put the right person on the pedestal. That person that does 150%, maybe they got the lucky lead. Maybe that former customer said, “Oh, Barry, I really screwed up. I should have never left you all. Now I realize why you all charge a premium.” And that’s the reason why they got 150%. You don’t want to put that person on a pedestal. But if you go into the inputs, you can really understand what’s driving that great behavior.

Then, the other thing that’s great for those top performers is typically when you’re looking at those inputs, you’ll find something that they could improve upon. So rather than giving them that pat on their shoulder, “Yeah, hey, great job, Sally. Keep it up,” you can actually go and really challenge them to be able to go and get better. Because at the end of the day, if you’re going to your top performers and you’re just patting them on the shoulder and saying, “Great job. Keep it up. Sorry, I don’t have a lot of time to go and talk to you. I got to go and talk to somebody else,” that top performer should leave your organization because you’re not making them better. But if you really understand the inputs, you can actually really go and help them become even better than they are.

Barry: Cool. Awesome. And you probably have a few of your friends or VP sales heroes. Without throwing any specific names under the bus, would you say that sales operations people are implementing this inputs versus outputs kind of measure, or would you say it’s still common to do more outputs?

Matt: I think it’s still very common to go and do the outputs, especially in early-stage companies. That’s what’s putting money into the bank, so it’s very easy to go and get fixated on that. But the problem with that is, it makes it really hard to go and get a repeatable outcome. A lot of times what you have is those early-stage companies where you’re only looking at the output and you don’t really know why that person’s successful. It’s just like, “Oh, they’re just really good. They really believe in this company,” or whatever it is, some sort of lackluster response. And then it actually hurts trying to be able to go and scale that company because now you’re trying to go and find the almost superheroes, and you’re actually creating a heroic culture rather than a repeatable culture. That’s going to be the company’s downfall until they can go and get out of that.

How big should my sales pipeline be?

Barry: Love that. Go for a repeatable sales process, not heroic. And then the other thing that is important to remember, is just that too many opportunities bring down everyone’s, not just the company’s sales, but also probably the sales rep’s sales because he’s not giving enough attention to the client or to the potential buyer. 

Matt: Absolutely. When I joined Trulioo, the first thing I did was, how many opportunities are in the pipeline? How long is their average sales cycle? How many touchpoints does it take? How much time do we actually have to go and spend with a client in order to go and get them across the finish line? And then it’s just simple math. Okay, they’re working 40-50 hours a week, so how many opportunities could they actually have in the pipeline? It’s pretty simple math to be able to go and back into that. And then you have an idea of how many opportunities should somebody have in the pipeline in total before you’re actually going to go and get really diminishing returns.

Barry: To follow up on that, you’ve worked at a few diverse companies, right? If companies have similar touchpoints and the average contract value is similar, is there a difference in the number of leads that they can handle?

Matt: It depends on that value how many touchpoints exactly. But a lot of companies, it’s pretty similar. Now, you get to big enterprise sales, it’s going to vary drastically when you’re asking somebody to go and close two or three deals a year, that type of thing. But in, say, a quarterly-driven model, if the average sales cycle has fairly similar touchpoints, give or take one or two or three ops, but it’s all pretty similar.

Barry: So can you give us the magic number?

Matt: Well, in a lot of jobs what I’ve seen, where it is fairly transactional, what we have found the magic number for us is, on a mid-market sales rep, is eight opportunities per month, or 24 per quarter for us with a conversion rate, once again depending on the inbound or outbound of looking at about 50% conversion rate, and then being able to go back into the math there. That’s been fairly common for mid-market, fairly transactional, but it is going to vary depending on the type of business.

The Art and Science of Managing the Sales Organization

Barry: So we were discussing scaling the sales team and we made it scientific. So now, selling is an art and it’s a science, but what about managing the sales organization? What about making sure that the whole sales department is scaling correctly and the teams are connected to the sales? How much science is involved in creating a scalable sales process? When I say science, I’m talking about putting inputs instead of just outputs and how much of it is an art, culture, or can we even bring culture to a science? I’ll let you take it from there.

Matt: Yeah. Both are incredibly important. And both are different, but they also coalesce together. So let’s talk about more of the science part. The other piece is that all departments need to be operating and moving in the same direction. So you start with, say, marketing sales, which is the obvious connection point. You got to be able to go and agree on that marketing funnel, and you got to have a handshake there that marketing is going to, say, develop X amount of leads, or whatever your nomenclature is. You call it leads, MQLs, SQLs, and all that kind of stuff. I still get confused about what everything means. But you do have to have clarity on the definitions and understand what the math is. There’s going to be this many on the top of the funnel, marketing may nurture to this extent, and then once this happens, it becomes a sales qualified lead, and there’s going to be this many sales qualified leads maybe flowing into the SDR side.

From the SDRs, now you’re going to have conversion rates. Maybe it’s content downloads, maybe it’s demo requests, maybe it’s emails or Drift or something like that. You’re going to have conversion rates on every single one of those aspects, and then that’s going to flow into how many opportunities are being produced to the sales team, which will allow you to be able to go and scale that sales team. Because at the end of the day, the only thing that matters is, are we putting revenue up on the board? And it’s not about they’re doing this and they’re doing that and you get these disagreements, but if you have this conversation and this agreement of what that funnel from the very top looks like all the way through, now we’re swimming in the same direction toward your revenue targets. And then you add the products in there. You’ve got products that are delivering new products and there’s an agreed-upon inflection point in terms of how much revenue that’s going to be able to go and add to the team. And you’ve got dollars behind what a successful product launch looks like. You’ve got products engaged with that, combined with new marketing assets and so forth into the sales side, and everybody is working together.

My current CEO, Stephen Ufford, he’s a product person. He’s an amazing gentleman. He talks a lot about whether you’re either in sales or you’re in sales support. Everything needs to be able to go and help our customers, that typically the output is more sales, either expansion or acquisition, having everybody with that mindset. But having math to be able to go and tie off all the way across is super important.

The Importance of Sales Team Culture

Matt: Sales culture is in my wheelhouse and I’m super passionate about that. And I learned that early on at Rackspace about the importance of culture. At the end of the day, at Rackspace, we were the plumbing of the internet. It was like the most boring part of the internet. We were going to a data center and taking a server and plugging it in, and on top of it plugging in a Cisco router and then maybe a firewall. And then if it was a big sale, you’d put a couple of servers in. It’s like anybody can do that. You talk about a commoditized industry. That’s driving down to the bare minimum. What was interesting is that Rackspace was able to offer value-led pricing and it was because no matter how great the technology was, customers still had questions. They still needed answers. We differentiate ourselves by offering the very best support in the industry. It wasn’t about the technology. We didn’t have really any differentiated tech whatsoever, but it was about delivering that best customer experience possible.

But in order to go and deliver that best customer experience, you better have a culture where people enjoy going to work and they want to be able to go and deliver that exceptional customer service. So we really focus on culture, building that community of Rackers and people, borrowing from Simon Sinek here, they wanted to go and volunteer their best. I talk about this all the time.

Every employee has a choice every day when they show up. You and I had a choice today, are we showing up, or are we volunteering our best? And when you go and create a culture where people want to volunteer their best, oh, man, the world’s your oyster at that point. I think that nowadays it’s even more important. There’s just war for talent out there, and people are constantly looking around. For most organizations, especially early stage, you’re not going to be paying the most out there. You probably don’t have the best benefits.

My brother-in-law works at a Fortune 500 company. Man, the benefits that they get, it’s crazy. It’s nuts all the things that they go and get, all the baristas making their personal coffee and the gyms and the personal trainers. I try to get in touch with him during the day, he’s like, “Sorry, we got a company-led yoga class. I’ll be back.” Sounds really cool. But in a lot of early-stage companies, you don’t have that. So you got to go and figure out, why should somebody go and join you on the journey? And I’ll tell you this. The answer, in my personal opinion, shouldn’t be, “Come and join us, and we’re going to go and have an exit in three years, or we’re going to go public in five years,” or something like that. That’s so short-term, and invariably it doesn’t happen. So then why should that person go and stay? There’s a company in Austin that it seems like every 18 months, they’ve been 18 months away from going public for the last eight years. And every 18 months they have this mass attrition because that was the value there. There’s got to be something more. And I think that really focusing on, how are you going to go and get people to go and volunteer their best?

We’re coming up on holiday time right now and you have a lot of holiday parties and so forth. I would say that’s not culture. That’s how you’re celebrating culture. Before everybody went remote, you had the foosball table, the ping-pong table, the video game, the pizza on Fridays, and the beer with the CEO on Thursdays. That’s not culture. That’s how you’re celebrating culture. But culture is really all about, how can you go and get people to come in and volunteer their best? How are you enabling them to do a great job? How are they learning? How are they growing? There are five great questions that I think every employee should be asking themselves. Am I learning? Am I growing? Am I having fun? Does my manager have my back? And do I believe in the mission of the company? You go and focus on those five things right there. That comes from Heather Brunner, the CEO of WP Engine. I don’t want anybody thinking I’m that smart. It’s just a quote from her. Am I learning? Am I growing? Am I having fun? Does my manager have my back? Do I believe in the mission of the company? You nail those five things, you got culture right there. You got people that want to go and volunteer their best every day.

The Challenge of Hiring for Culture

Barry: Did you find when you went from one to 150, was there any point where it becomes more challenging to hire for culture? Was it ever challenging after you hired them, where the culture shifted and there were some things you weren’t expecting, even though they fit your core hiring values when you hired them?

Matt: It’s always a challenge. At every stage, it’s a challenge. But culture is one of those things that’s also not top-down. It can’t just start with the CEO. It has to go and start with everybody. It has to start with everybody believing in the mission of the company so they want to go and volunteer their best. It’s not, “This is what my paycheck is going to go and look like,” or that type of thing. But it’s really about understanding the mission, understanding the strategy, getting people to go and believe in that strategy, understanding where they participate in the execution of that strategy.

What Advice Would You Give to Sales Leaders?

Matt: I also think part of that culture as you continue to go and scale out and get bigger, is learning as a leader, I don’t have to have all the answers. Sometimes, especially early on or first-time sales managers, it’s like, “Okay, this is why I got put in this position. I’m supposed to have all the answers.” That doesn’t scale, that doesn’t work, and actually it’s not true leadership. It’s your ability to go and get the answers out of the people and bring them up to the service. That actually really builds confidence.

I’ve talked to so many, especially first-time managers or mentors, and they start saying, “Matt, I don’t know how to do this. I’ve only got four or five people and I can’t do this anymore. I don’t understand how I can scale to seven or eight or nine people.” And when you dig into it, the reason why it doesn’t scale is because they’re giving people the right answers. Somebody says, “Yeah, hey, Barry, you’ve been here for a while. You just got promoted. You’ve probably seen this over and over. This is what the customer said. What should my response be?” And the worst thing that you can do is to say, “Hey, say this, do this. Then they’re probably going to say this, and then when they do that, do this. And boom, you’re going to be able to go and send out a contract,” whatever that is. In this case, it’s sales.

Now sales rep goes back and says, “Wow, Barry is great. Man, if I hadn’t gone to Barry I would never have closed this deal.” And you go home and you’re getting to see your newborn baby daughter and you’re saying hi to your wife, and you think, “Man, this company’s so lucky to have me. We would’ve lost that deal.” And then the next day, guess what? That sales rep’s back at your desk. “Okay, Barry, I got another one,” and then, “Barry, I got another one.” Now they don’t have any confidence. They don’t know how to go and think for themselves. Great leaders take a few more minutes and say, “Well, what do you think?” And if it’s not a very good idea, you say, “That’s interesting. What’s another way to go and approach this? What’s another way to go and approach this?” You avoid that transfer of ownership and you build up the confidence in people, so there are not as many people coming to your desk because they have that confidence in themselves. And that’s something that’s super important as you continue to go and scale.

Barry: Yep. That makes sense. And that almost sounds like it couldn’t even be a science versus art versus it’s something you have to work on. And you don’t see the numbers. But in theory, you could put that into numbers. How many people are coming to me? How often are they coming? How much time are they spending? And then how much time are they doing these things by themselves? We don’t think it’s science, because we don’t see it. It’s not in our CRM, right? But the data can be worked on and worked on into a science.

Matt: Absolutely. As a sales leader, leave your ego at the door and spend the extra few minutes bringing the answers out of people. Because also, at the end of the day, as a leader, how many customers are you actually talking to every day versus your ICs? They really know what’s going on. And maybe you got to go and help kind of bring those answers out of them, but it’s worth that couple of extra minutes and that empowerment and that confidence that you build within the team. That’s something that you can go and scale.

The Pressure on the CROs of Startup Organizations

Barry: As a CRO, you have lots of teams. You have your sales team, you have the implementation team, the customer success team. And then you also have all this pressure, not necessarily from your CEO, but from just startup pressure of trying to grow quickly, like every other startup. So tell me about some of that pressure. Tell me about what that pressure sometimes does to teams, whether it’s something you’ve experienced or you’ve heard. Obviously, stories are more interesting. And we’ll take it from there.

Matt: Yeah. Absolutely. And this is something that I’ve been thinking about quite a bit lately. There’s always pressure, but I think that most companies will have, at some point, their go-for-it year, and typically it might involve a round of funding. You follow the red pill, you take the cash, but now you got to go and run like heck. There’s a lot of even greater expectations. I’ve experienced this a couple of times on a big round of funding. Also experienced it on a run-up to an IPO a couple of times, and this is our big go-for-it year and so forth. There’s always pressure, but there’s always that one year where the pressure really, really, really mounts.

What’s interesting to me is if you went back in my career and you went to that go-for-it year in each of the companies that I’ve worked at, everybody puts together this risk slide. It’s like, “Okay, this is our go-for-it year, but let’s understand the risks.” And the risks are all the same. If you went back to every company, you could use the exact same slide. The risks are something around products. We need a couple of new products, or we need our product to mature a little bit or something, but there’s always a couple lines around the product. Couple lines around marketing execution. We need to do a better job marketing. We need to go and create a bunch more opportunities. We’re not quite sure how we’re going to put some more money on there because we just got some funding, but we got to go and find that.

Then you got sales execution. Can we continue to go and refine and go and get more efficient on sales? Then there’s hiring. Are we going to be able to go and fill and put butts in all these seats right here? And then there’s attrition. Now we got the butts in there. How do we go and make sure that they don’t leave? It’s typically those five things. And there might be some engineering pieces on that, but you got people in culture, HR, on the hiring and the attrition side, and everybody’s in it together. And you might have a couple macro conditions that you throw on the list just to show the board that you’re really understanding the macro conditions. But you can’t control the macro conditions. And everybody signs off on this and says, “Yes. Okay,” and then you go kind of bullet point by bullet point, how are we going to go and make sure that we cover these risks and so forth?

But what I figured out and particularly for a long time, that’s not the biggest risk. None of those things that you write down will be the biggest risk. The biggest risk as that pressure mounts is that you have fragmentation within departments, and it’s for the first time that the company is no longer marching in the same direction. But for the first time now you have departments turning on each other. I’m doing a good job. It’s all of those folks over there. I’m doing a great job in sales, but it’s the product team. That’s why we’re not missing. And the product team is saying, “Well, we didn’t get enough support from engineering,” and marketing is saying… doing a horrible job, but marketing’s hitting their numbers and so forth. That fragmentation is what kills you.

And so as you’re putting together that risk and you got that go-for-it year, yeah, absolutely cover the product risk, cover the marketing, cover the sales, cover the hiring, cover the attrition risk. But you got to go and make sure that everybody is on the same page and we’re all marching in the same direction, just like you were all the way up to that go-for-it year. The minute that you have finger-pointing, you do not wait a moment until you jump into that and you crush that and you squash it really quickly. You talk about it on that lead-up to it, because it’s going to be tough. There’s going to be a lot of pressure and high expectations and so forth. It’s really interesting to see human behavior happen. In every company that I’ve worked at when there’s that go-for-it year, that’s been the biggest number one risk. That’s what you have to avoid, making sure that everybody is supporting each other and all marching the same direction and you don’t elicit that one department pointing fingers at the other.

Barry: Yeah. No, that makes a lot of sense. So one piece of advice you just gave was to squash it right when it happens. Is there anything we can do to squash it beforehand?

Matt: Yeah. At Trulioo, right now, we talk about it all the time. We closed a great round of funding over the summer from TCB, their largest investment ever. Huge opportunity for us, massive opportunity. The TAM is so expansive. It’s only growing. It’s global. Our product is incredibly sticky. There’s just so much to love about this business. And look, now we’re coming into 2022, and this is our new go-for-it year. 2023 will be another go-for-it year. But this is our big go-for-it year. We’ve got all the same risks, but the most important thing is that as an organization we stick together and we got each other’s back. And as long as we go and do that, it truly is going to be incredibly successful. We’ll figure out the product, we’ll figure out marketing, we’ll figure out sales, we’ll figure out all that kind of stuff. And it’s not going to go and run perfectly, but as long as we’re going and doing it together as a group, I’ve got no doubt we’re going to be incredibly successful. But that’s so important.

So, yeah, we talk about it a lot, but it also goes back to the metrics. Let’s make sure that we’ve got these metrics that we’re aligned in what success looks like. But the overall success is, how are we growing this organization? Nothing else matters if we’re not delighting our customers and our prospects every single day. Let’s also be really clear about that as well.

Goal Framework for Scaling Revenue Operations

Barry: Right. So it sounds like conversation, making it on top of mind so then if there’s even a tingling, you could quash it right away before even people realize that they were doing that. Does your team use an OKR framework, or is there a goal framework that everyone’s aligned on, or it’s more of an Excel.

Matt: There’s definitely a whole framework as well. And the other thing too, Barry, is I’m a people person. We got to go and get people together, sometimes virtually like this, and sometimes, every once in a while, you can go and do it in person. I know you’re in the office today, running into people. But as you get bigger and bigger, sometimes departments start to go and head off and just do their own thing, where it’s a lot smaller company-wide. There’s nothing like human relationships. We’re going to go and do a virtual happy hour. We’re going to go and do an actual lunch in person. Let’s make sure the product people are there, let’s make sure the marketing people are there, let’s make sure implementation is there, and let’s not just make it our own department thing. Even little things like that, they really matter and they’re important.

Sometimes at earlier stage companies, those just happen naturally. Heck, I’ve even seen at Rackspace, we used to sit together all on one floor. We were super small. Everybody could hear what they were talking about, and the sales people were like, “Man, those support people are amazing. They do so well,” and the support people were like, “Man, it’s really hard to go and sell. Those folks are doing a great job,” and so forth. Then we got bigger and we had to go to two floors. Guess what happened? “Man, what the heck’s support doing? What the heck’s sales doing,” and all that. It was just moving a floor, and we really had to go and focus on that and bringing those teams back together. Everybody walk a mile in each other’s shoes.

The Impact of Giving Back on Company Culture

Barry: Yeah, love that. I also love that you’re bringing up Rackspace for culture. There was someone a few years ago in Israel named Allen, and maybe you overlapped with him. His whole goal with, he worked for Rackspace, was to just give back to the people, help startups succeed, even if they weren’t using Rackspace. I totally agree with the culture. I never sat with him for more than 10 minutes, but I already felt the Rackspace culture, even though I never met him for more than 10 minutes. That’s great.

Matt: It’s amazing to see some of the former Rackers and what they’ve done to be able to go and help support local communities. I think the lesson there too is to be generous with your time. Even if you don’t think that it’s going to directly impact you, make time for people. Be generous with your time. It comes back to you tenfold, but be generous.

At my conclusion in my Rackspace career, I took 18 months off and I formed a nonprofit and spent a lot of time in Southeast Asia and tried to give back, teaching English to novice Buddhist monks and orphans in Cambodia, and ultimately Myanmar, building schools and orphanages and playgrounds. I like being generous with my time, giving back. Yeah, guess what? I got so much more back to me than I could have ever done for the people that I was trying to go and help. It was actually almost arrogant of me, like “Here I am. I’ve been successful. I want to go and help these people out.” And the level of guilt that I felt during that time was immense because it was just – I learned so much about what’s important in life and learned so much about myself through these people that I was trying to help. It turned out they were the ones that were helping me.

Barry: Love that. That’s awesome. That’s really a cool experience. We’ll have to do a different podcast just on that experience. So we covered a lot today, how to go from sixth grade teacher to CRO, from one to 150 on the sales team, to disgruntled, maybe that’s a little too intense, but not happy employees to happy employees. I think our listeners really appreciated all this information. I think it’s important as we go into 2022 and we’re doing projections that people think about the people and not just projections. But when you can make something scientific, try to do it earlier than later, not just outputs, but also inputs. That, I think, is gold, as well as connecting with people. I love all of this.

Matt, thanks so much. Before we go, maybe tell me a book you’re reading or one of your favorite books. Something I ask all of our podcast guests.

Matt: Yeah. A buddy of mine, Lorenzo Gomez, wrote an awesome book called Cilantro Diaries, and I recommend that everybody read that book. He has been incredibly successful, and without a college education. He talks about, in the absence of college education, how did he go and get there? And if you got a PhD or you’re a high school dropout, it should be required reading. It’s an incredible book.