Exiting three companies, moving from individual contributor to leadership, and telling a story with numbers with David Greiff (CRO at PlayOn! Sports)

Callan Harrington 00:01
You're listening to "That Worked," a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here.

Callan Harrington 00:21
We have David Greiff with us today. Now, when you look at David’s profile on LinkedIn, this guy has done literally everything—from co-founding a company to working for a large company like Oracle. He’s got three exits to his name across private equity and venture capital. David, you've pretty much done it all. Welcome to the show.

David Greiff 00:40
Thank you, Callan. I really appreciate the time.

Callan Harrington 00:42
Absolutely. So why don't you start by telling us what you're doing right now?

David Greiff 00:48
Yeah, so right now I am CRO of a tech platform that's focused on the high school and K-12 space. We provide ticketing to high schools and middle schools, and we also provide a streaming service to high schools. So if you want to go to the game, we can provide the tickets. Or if you want to watch from home, we do the streaming.

Callan Harrington 01:10
Gotcha, absolutely. Now, I know you guys have been growing for a while. Before that, you were acquired by KKR and had an acquisition with a couple of companies. So what's kind of the ballpark size of the company? How many employees do you guys have right now?

David Greiff 01:28
So right now, we're a little over 300 employees—full-time and part-time—but about 200 full-time, 300 with the part-time folks on the service side.

Callan Harrington 01:40
Great, great. So we'll dive into some of that. To kind of kick everything off, how did you get here? What brought you to where you're at today?

David Greiff 01:48
That is a good question. If you go all the way back to when I started, I had two paths—either go down the consulting path, which a lot of my friends did, or go down the sales path. I chose door number two. I don’t know why, but I ended up becoming a salesperson, which turned out to be a pretty good decision in the long run. I started as a sales rep slinging telecom equipment, and from there, I kind of worked my way up and did a lot of different things to get me to be a CRO of a combined org of close to $200 million in revenue.

Callan Harrington 02:20
Now that’s incredible. So you could have gone into consulting. Why not? Why did you choose sales?

David Greiff 02:28
I was the social chairman of my fraternity when I was about to graduate, and I had to convince this sorority to be our partner. I just thought, "Man, I’m really good at convincing someone to do something." So, I convinced them to select us as their partner for homecoming, and the light just went off. I thought I could be really good at selling and convincing. Of course, selling is a lot more than just convincing people, but that was the light bulb moment for me, and I decided that would be a fun career.

Callan Harrington 02:55
And you wanted to move to Atlanta after the Olympics, right? What was it about Atlanta that excited you?

David Greiff 03:03
It was just overall, like, the crazy growth that I was experiencing. Post-Olympics, a lot of people were moving here. It’s a silly answer, but a lot of my friends were moving here, and there was this opportunity to go to a city that was experiencing exponential growth. It made a lot of sense. It’s a young town, and I wanted to be in a place where there were lots of young professionals like myself. It just seemed like an easy city to live in, and I figured at some point, I’d probably have to travel for a job. Living in Atlanta, you can get pretty much anywhere in the world with one flight, so that probably nailed it for me. And the weather is great as well.

Callan Harrington 03:40
That is so true. Of course, in Columbus, Ohio, right? We do not—Atlanta is unique in that it’s got the biggest airport in the world. But in sales, it’s a huge convenience to be located close to a place like that. I think it doesn’t get talked about enough—the difference between getting a direct flight and having a layover in a sales role. In my opinion, it actually does make a difference. How do you feel about that?

David Greiff 04:06
100% because I can do a day trip versus having to spend two days, or I can get in and out of a meeting. I don’t think that happens as much anymore, going for just one meeting, but before the pandemic, you could fly, and I could be in New York for the morning and leave that afternoon—really anywhere minus the West Coast. So I think that’s huge. And when you’re leading large teams like I’ve done in the past, being able to get out of the city and get back home and go to the next place is really important. So I was probably—I don’t know if I really thought about that much when I was that young, but it definitely paid off as I was traveling the world to work with my different teams.

Callan Harrington 04:48
Yep, it makes complete sense. So you started off as an individual contributor, as a sales rep. Were you selling to enterprise, SMB, or SMB?

David Greiff 05:00
I was. It’s a funny story. I was selling telecom equipment, literally knocking on doors in buildings and getting chased out of buildings. So whenever one of my sales reps complains about not having enough leads, I’m like, "Dude, I had the yellow pages as my lead book." Then I would just knock on doors and ask people what they were doing for their telecom—what phone systems they had, or what long-distance carrier they had. It was hard but fun, and I was pretty good at it. I don’t know if it was the timing—it was right before the bubble—so maybe that helped, but I ended up being a pretty good little sales rep, knowing nothing. I knew nothing about sales besides selling my fraternity to a sorority for homecoming.

Callan Harrington 05:36
I love that that was the spark that did it.

David Greiff 05:39
It’s a truthful answer. It’s funny—I got into sales because my best friend went in to interview at Northwestern Mutual to be an insurance agent for their intern program, and they asked him for a referral. I was the only number he had memorized, and I had no internships lined up whatsoever. I remember I picked up the phone—I was hungover when I picked it up, probably sounded terrible—but I picked it up, and they were like, "Hey, this is Northwestern Mutual." I thought it was one of my friends prank-calling me. I didn’t take it seriously, but sure enough, that’s what got me into it. It’s one of those things where nobody I know—very few people—says, "I just can’t wait to graduate and get into sales."

Callan Harrington 06:20
Yeah, that’s awesome. I love that. So when you were an individual contributor, was there anything in particular—whether it was a habit or something you were doing—that led to your success?

David Greiff 06:32
My first sales manager was really good. I got really lucky to have a good sales manager and coach. It was all about preparation—knowing your client before you walk in the door, not when you’re cold calling, of course, because when you’re just knocking on doors in a big building, whoever opens the door is a good thing. But it was just not being afraid to lose. I know that sounds kind of simple, but he said, "Put 10 pennies in your pocket." I tell this story to this day, and I think it goes over well. Put 10 pennies in your left pocket, and when you get to the ninth penny in your right pocket, you’re going to close the deal. Every time you get to the nine no's, you’ll get to the one yes. I think that just helped me put it all in perspective. It’s okay to lose—it’s a lot of just sheer will. You learn to be a better salesperson and start reading books and all that sort of stuff, but in the beginning, it’s just about working as hard as you can and working smart at the same time. If I wasn’t having a great day or didn’t have a lot of meetings, I’d pick up the Yellow Pages and start banging out phone calls. I did that enough that I was, like I said, pretty successful.

Callan Harrington 07:55
It’s one of those things. I’ve found this—I don’t know if you’ve seen this—but I’ve found that at every single stop, that 10-3-1 rule. You talk with 10 people, 3 will give you the time of day, and 1 will become a client. It’s ridiculous how much that still adds up. Now, of course, large enterprise is different, and micro SMB or B2C is different, but as a whole, that ratio is really interesting. I love the 10 pennies, because correct me if I’m wrong, but essentially, it’s what tasks are going to move the needle the absolute most, and how do we make sure that we’re holding ourselves accountable to them?

David Greiff 08:34
Yeah, and when you’re a young rep learning how to sell, you need to have an easy target that you can focus on every day. I tell the younger sales reps that I don’t spend as much time with as I’d love to because I have sales managers and all that, but imagine you’re at a bar and you’re going up to 10 different ladies or men or whatever you’re into, and by the 10th one, someone’s going to give you their phone number. If you treat it like that—as a game and you gamify your own world—it can kind of work.

Callan Harrington 09:05
No, I agree. Whatever it is, whatever kind of goals you need to lay out there, that’s one of the things that’s hard, right? I’ve maybe seen very few people who are like, "I can’t wait to cold call. I can’t wait to go knock on doors today." One of the best quotes I’ve ever heard is, "Successful people dislike doing the same things that unsuccessful people do, but they do it anyway, and they do it over and over again." So you were a good sales rep, yes. When did it happen along your career that you made that leap into sales leadership?

David Greiff 09:46
Well, after I did that, I moved up pretty quickly and was running the state of Georgia for that company, that telecom company, as a sales manager. I was like 24 years old or whatever, so that was my first time managing older people than me. That was a big lift—learning how to manage people and not doing all the selling myself. I did that for about a year or so, and then I had an opportunity. My life has been a series of paths, and I picked a lot of good ones and some not-so-good ones, but I had an opportunity to join Sun as a sales rep. This was pre-Oracle purchase, which is kind of funny because it’s full circle—I ended up at Oracle anyway. But it was either go to Oracle or start a company with some seed capital, and I figured since I could manage a sales team, I could certainly start a company.

David Greiff 10:27
Of course, I was way off, but I thought I could do it. I ended up saying, "Alright, I’m going to go start this company," which was a vaccination services company that was about 10 years too early. It would have been a great business a few years ago, but I started a vaccination services company in a small little office. I knew absolutely nothing about vaccinations or healthcare, minus my dad being a doctor. That was as far as I went, but I kind of treated it like a telecom company too, which had some good things and some bad things. But I was able to build a nice little company for nine years.

Callan Harrington 11:00
So before we get there, because I want to dive into that a little bit more, I think a lot of the listeners will find that interesting. You mentioned a key point in particular, and this is one that I think a lot of people, especially new leaders, struggle with—starting to manage people who are older than you. When you first started doing it, what were some of those concerns or fears? I remember mine. For me, it was like, "Are they going to take me seriously? I’m 10 years younger than this person. What am I going to teach them?" What was that like for you?

David Greiff 11:33
That was the hardest thing for me—how am I going to teach these guys who have been selling for five or ten more years than I have? And do they think I just got moved into this role? I had that—I forget what they call it now, but—

Callan Harrington 11:50
Imposter syndrome?

David Greiff 11:51
Yes, imposter syndrome. But back when I was first getting into this, that wasn’t talked about. I literally thought, "I’m not qualified to do this." Every day I woke up thinking that, and it just made me work harder, learn more, and read books because, back then, I’m going to date myself, there weren’t podcasts to listen to. There weren’t all these outside sources where you could go to get information. So I just made myself read as many terrible management books as I could so that I would at least, in my mind, provide some value to them. But then when you peel it back, you realize they picked me because I was doing really well. But not all good salespeople are good managers—that’s 100% accurate. So I think that was part of it. But just teaching myself how to be a good manager and how to help them be more successful. One lesson I picked up was that my only job, and I’ve said this to lots of people, is to increase their W-2. So I focused on how to get them more leads and all that sort of stuff. It worked, but it was definitely hard. I’m sure there were some reps who couldn’t stand me because I was this young, snot-nosed kid running a team. But it is what it is, right? I don’t know where those people are in their careers now, but it’s hard. It’s really hard. And that happened to me at a couple of stages along the way, even at Oracle.

Callan Harrington 13:05
No question. I found it very similar because, again, it’s one of those things that doesn’t really go away, right? That first time managing somebody who’s older than you, and then you realize people are people. It doesn’t matter. And that’s why diversity actually helps so much, because you get different thoughts, different opinions, different things like that. But I didn’t understand that as much earlier in my career. So you went on, co-founded a company. What drove you to do that? What was going through your mind at that time?

David Greiff 13:36
I don’t know. I wanted to do something on my own because my family has several entrepreneurs, and I figured that’s the quickest way—I mean, again, I was young—to make a lot of money and go live on the beach for the rest of my life. So that’s probably not a good reason to do it. I didn’t have some mission to go vaccinate the world. Usually, when someone starts a company, they’re on some mission. I did not. I was thinking more financially, which is probably not the greatest idea in the world, but at least I’m honest—that’s the way it was. So that’s what I was coming out of college thinking, "Okay, I want to go make as much money as possible."

Callan Harrington 14:13
Yeah, it was until years later that I started making decisions for fulfillment, energy, things like that. And you realize a lot of times the money does tend to follow, depending on your career. But you got in here, had this family of entrepreneurs, and thought, "Okay, if I want to relax at some time in my life, I need to get after it right now."

David Greiff 14:35
Yeah, I had a dream of retiring by 40. Obviously, that didn’t happen, but that was my dream. Then I thought I’d go into politics randomly. So neither of those happened. But I saw a need, a little bit of a need. And once I got into the business, I knew that I could outsell the local guys and make this a national-scale company. And so we did. It’s crazy to think about it now, but of the Fortune 50, I think 20 of them were my clients where I was going out providing. Yeah, it was nuts. It was sheer will again and using some of the sales tactics I picked up along the way. Then I had to build the infrastructure. That part is not natural to me, building the operational piece, so I had to really learn that. But we were pretty darn successful and ended up learning how to delegate, which has helped me along the way.

Callan Harrington 15:20
If you don’t mind, I want to reverse for a couple of those things. So another transition that you made was going from SMB to enterprise. How was that change?

David Greiff 15:30
I didn’t really—I think looking back, there’s a massive difference. But in my mind, it was a one-to-one. I was calling the HR person, the head of HR, or the head of health and safety. So for me, it wasn’t that—until you asked that question, I never really thought about that transition there. Obviously, now I know there’s a massive difference because I’m probably smarter, so maybe what I didn’t know helped me. I treated it more like, "Hey, I’m going to go meet some receptionist and then get her to have me talk to the office manager so I can go sell some telecom equipment." And that’s kind of how I used this—"Alright, I’m going to call every single HR person in all these big companies." You can find them. It wasn’t that hard to find them and convince them to outsource their vaccinations and health fairs to us. So it’s probably good that I was young and didn’t know the difference because I don’t think I had any idea what enterprise or small business was. It was just sales.

Callan Harrington 16:30
Yep, now I’m jaded.

David Greiff 16:33
Yeah, 100% know the difference now. There is an absolute difference in how you sell—using MEDDIC and MEDDPICC and all that sort of stuff. But yeah, that’s a great question. I just did it.

Callan Harrington 16:50
I find that super interesting. Here’s why—even as we’re talking about this now, I think about it because I did something very similar, and I didn’t think about it any differently. I didn’t think about going into it with all this different structure. And I’m a process person, right? So I like that structure, but I do sometimes think, especially in sales, especially as you’re scaling, that sometimes we try to over-engineer it. A lot of times, it’s just, "Okay, let’s go." Especially when you’re doing a new market or something like that, let’s go, let’s figure it out, see how it is. And it sounds like that was pretty similar to the approach that you took. As a result, you just said you had massive success. When you get 20—what did you say, 20 out of Fortune 50? That’s pretty insane.

David Greiff 17:35
Yeah, crazy.

Callan Harrington 17:37
Okay, so you’re at this startup, and you were there for almost eight years, right?

David Greiff 17:41
Yep, we ended up going out and raising some capital, which was my first foray into the world of VC and someone else’s money. I mean, we had some seed capital from my family, but yeah, we went out and did the tour and ended up raising some capital from a VC firm here in Atlanta. That was a whole different world. Now you have someone else asking questions, which was different for me because before it was just me asking my own questions in my head, right? But now I had some really smart people asking questions like, "Why’d you do this?" or "Do you think you should go faster here or slower here?" That was actually really interesting. It was a good experience.

Callan Harrington 18:23
It makes sense. I know that’s a hard transition for a lot of people, and some people will try it and go back to being bootstrapped because they find that they don’t enjoy it that much.

David Greiff 18:34
Yeah.

Callan Harrington 18:35
I think one of the interesting things about your career is you’ve got these different perspectives because you’ve done it all—whether it’s private equity, VC, bootstrapped. What were some of those early learnings that you found as you started to both raise capital and then after raising capital, working now that you have investors that have a vested interest as well?

David Greiff 18:57
Know the story and be able to tell the story with numbers. It took me a little while to get this right, but being able to tell the story with numbers is critical because, at the end of the day, a professional investor hears the story, but they’re really focused on the numbers because that’s what they do. They crunch through numbers and see things that you could never see. So being able to efficiently tell the story but also have the data or numbers behind it is critical. I didn’t know that in the beginning, and so it took a little while for us to hit our stride, but learning that is critical, and that’s served me throughout my career. Less about having the story short and quick, but being able to tell it with metrics and numbers—that’s critical. If you can’t do that, it’s really hard to move up the ladder, if you will. So that was great. I learned it on someone else’s dime, essentially.

Callan Harrington 19:47
I think that is a big piece, and I’ve actually never heard it described that way—tell the story with the numbers. When you think about doing that, what’s your process for doing that?

David Greiff 20:00
It’s a really good question. Metrics and numbers don’t lie. If you can look at what you’re trying to do and, for instance, if you want to show the TAM, go get the data and show, "Hey, look, this is how many in that world, Fortune 500 companies." That’s an easy number, but how many Fortune 500 companies with multiple locations, which was our sweet spot? So being able to back everything you say with numbers, or if you’re looking at your forecast, like, "Okay, here’s why I’m going to hit my forecast. This is my pipeline. This is what I expect to close." As long as I can show the story without me being in the room—maybe that’s the better way to say it—as long as I can provide the numbers, and someone who’s not in the room is looking at my data and they get it, then I’ve nailed it. The story only lasts so long, and in that world, we’re talking to 100 people a day. So you might be a good salesperson, which I think I’m pretty decent at, but if I can give them the numbers or the printout, they should still be able to tell the same story. That’s when you know you’ve nailed it.

Callan Harrington 20:58
That’s excellent. If I’ve told this story well enough, I don’t have to be the one to tell the story. They can look at the deck and see exactly how we derived this and why we have confidence in being able to achieve this.

David Greiff 21:10
Yeah, because they’re probably talking to slick salespeople all day long, right? So it’s more about the numbers. As long as the numbers tell the same story, and if you have them both hitting, that’s gold. If you can tell the story and have your numbers back it, that’s a home run.

Callan Harrington 21:29
That’s excellent. I love that. I love that. So you’re at this startup, you raised some money, and then I know you went to, I believe, EBIX after this?

David Greiff 21:41
I did.

Callan Harrington 21:42
What was that transition like? Walk us through that.

David Greiff 21:46
Yeah, let’s say it was really difficult because you went from running your own company to working for somebody else, even though you kind of work for someone else in the world of VC. But it was time for me to go. I made some really good decisions and really some bad decisions. If I could go back now, I would have taken that company and sold it five times, but I just didn’t know. I was too young and didn’t have enough experience. So maybe that’s one of the pitfalls of starting companies so early in your career. But working for someone else and working for a company—I had 60 employees at the max, and this was 1,500 employees—was a massive difference. I was, again, young. I was leading two teams, and we did two acquisitions. I ended up having four different sales teams underneath me. That was definitely challenging too. I had never done an acquisition, and I hadn’t been in a company that would buy and then cut everything. So that was totally different for me as well. It was a tough learning experience, but we were pretty good. I mean, we had a successful team, and I changed some things and trained the sales team up. That was more of an enterprise-type sale. That’s where I started really understanding, like, holy crap, there is a massive difference between selling telecom solutions to a small business and selling a large solution. I quickly learned the difference. Again, I don’t think there were a lot of podcasts there, so I was reading a lot of sales books and trying to train the team up. It was definitely challenging. It was hard in the beginning.

Callan Harrington 23:17
So let’s talk about the enterprise sale a little bit. What is it that you have found that really needs to be in place, let’s say from a team perspective, because it’s harder to see those nuances if you’ve got one person, and that person is you, going out and getting these clients? But when you’ve got a team and some of that rigor and process around it, what are some of those things that you believe need to be there to be successful?

David Greiff 23:45
Well, first of all, it takes a full team. I firmly believe it starts with content. You’ve got to have a content-producing machine. Wherever I go now, that’s one of my first hires—go hire a badass content person who can write and build because that pulls through to all aspects, from sales to marketing to CS to service at some point. It’s a full-on team sport. Start with the content person, obviously marketing. I think of it as almost like the funnel. That’s how I go build my team. I’ve got to have enough leads, MQLs, and SQLs to feed my organization. So I always start there first because I know if I can build that and it’s working, if I can get that engine to work, the rest will follow. That’s where I’m saying it’s fully a team sport. The way I structure my team, everybody knows what the revenue number is, and we’re all tied to that number. So from marketing to the content person, we’re always talking about where we have to go from a revenue growth perspective. If you can do that and nail that, then it works really well. Then obviously, you need a BDR, SDR team that will help the sales reps get in front of the right people. I don’t want my sales reps spending all their day prospecting. I’d rather have them in front of qualified prospects, especially from an enterprise standpoint, because those deals are so long and sloggy. If they’re sitting there picking up the yellow pages all day long, they’re not in front of enough customers. That’s not a good thing. They’re too highly paid to be doing that. Then just having a structure around how you manage the opportunity. I’m kind of high-leveling it a little bit, but I’ve always liked MEDDPICC over MEDDIC because I think the paper process is something that kills every sales rep, big enterprise in particular. Working in a place like Oracle, you can’t really miss forecasts, so you have to understand that process of how long it’s really going to take to get through their entire internal process. So having MEDDPICC, and then obviously having a good CRM and all that sort of stuff to track it, is important. But in my mind, it really starts with content. If you can get the content right, it goes all the way through.

Callan Harrington 25:54
Let’s zero in on that because I think this is something I don’t want to say is unique, but I think this is something personally that doesn’t get talked about enough when it comes to enterprise sales. Walk us through—what’s your process when you look at content from an enterprise sales perspective? What are you looking for? What does that process look like? What kinds of content are you building, and how is that deployed?

David Greiff 26:22
It’s everything about the industry and surrounding industry so that I can use that. It could be anything from a blog post to the website to just that the whole machine is using the same language and the same vernacular, if you will, for all parts of the process. So building the entire "why you should work with us," here are some interesting stories. It’s not always super salesy; it’s more about being informative. I’m a big believer in informing the customer, educating the customer, and they’ll come. But you’ve got to be salesy enough—it’s a tricky thing to hit. There’s definitely a fine line—salesy enough to get their attention, but informative enough so that people think you’re a good source of information and they’re going to reach out to you. Especially in enterprise, you’re not going to cold call someone and they’ll say, "Oh yeah, I was thinking about spending $10 million tomorrow. I knew there was something else I was working on—what was it?" That’s different. So you have to build that machine so people are like, "Holy crap, these guys know what they’re talking about. I’m going to call them when I get to that point." Without good content, none of that happens because I’ve seen places where they don’t invest in content, and it’s a lot harder to get those meetings. It’s all about that piece—it’s an art, and I could never be that person, but I know what I want. I can just tell them, "Hey, we need to go build this machine." Literally, everything we do is derived from that content—our CS material, our sales material, going to a trade show, whatever. All of it is the same because we want that message to be clean and crisp.

Callan Harrington 27:55
I love that. I love that. So you mentioned Oracle, and you mentioned specifically that you don’t miss forecasts at Oracle. Walk us through—what’s that mean?

David Greiff 28:07
Yeah, so when you go to Oracle, they are a machine. I tell the reps who work for me that at some point in their life and career, they’ve got to go work for one of the big boys because you learn so much around metrics and KPIs and how to forecast. When I say forecast, at the beginning of every quarter, you say, "Okay, I’m going to close $6 million, whatever the number is. I’m going to forecast $6 million of it. I’m going to put upside $3 million of it, and then there’s the pipeline of a million." Whatever that forecast number is, come hell or high water, you better damn well get that number because that all rolls up to the unit, and the unit rolls up to the GM of a massive unit, and that rolls up into headquarters. So you have to be really good at taking your pipeline, understanding your pipeline, working with your reps, and nailing your forecast. You just don’t miss it. If you miss the forecast, it’s a bad day at Oracle. Oracle is very quarterly-driven, so that whole process starts over every single quarter. You learn really quickly. I had a boss there who was the GM of a $2 billion unit, where his thing was, "Don’t use adjectives when you’re on the forecast calls," which is a really hard thing to do. I’ve tried taking that to other places, but it’s a little—

Callan Harrington 29:24
What’s that mean? Do you mind walking us through that?

David Greiff 29:27
Yeah, this is a great deal. I feel really strongly about it. It’s more about, "Here are the next steps. This is the date this is happening. This is the date this is happening, and this is it." So take all the emotion out of being sold yourself and just give them the data. It’s kind of like full circle back to when you’re reporting to a VC—be able to tell the story without any story. You can tell why it’s happening, but the underlying baseline is it is happening on this date because we have a meeting here, they’re going to budget approval on this day, they looked at these three competitors, and the reason they chose us is this. So understand your deals, and you learn that at Oracle. As a leader, and I was running the Americas for the insurance and healthcare unit, you’re forecasting all these different deals, so you’ve got to know your deal. Not using adjectives is hard, but you become pretty good at it.

Callan Harrington 30:22
Now that’s excellent. It cuts right to it. As a sales leader, I’ve done it—I’ve seen sales reps put artificial importance on certain things, a KPI, a deal, whatever that may be. I actually love that as a rule. I’ve never heard that. I really like that. So you’re at Oracle for a few years, and then I know from there, this is when you went on this tear of exits. You had multiple exits throughout the last three companies that you’ve been with that had significant acquisitions. When you look at those, is there anything you think, "This is what we did here, here, and here," or is each one unique?

David Greiff 31:10
They all have some uniqueness to them, but they all—the first one was about rebuilding a sales team, culture, and structure. It was a flat organization, meaning flat growth, and we had to rebuild the way we were thinking about attacking the market and hiring different types of people. I didn’t fall into the trap of always hiring someone who’s been in that same space for 100 years and has a Rolodex of 600 pages. I think that’s total bullshit, personally. I think you can hire and train people. They need to know the industry a little bit, so restructuring that team, and you can train them up on the intricacies of artificial intelligence or machine learning or whatever you know. But you need someone who’s going to follow that process because I know the process works. The process starts with content, starts with making x amount of calls, working with people, working with the SDRs, and trusting the process upstream. That was the first one. So that was more about restructuring. The second one, I was lucky—it was already a fast-growth company, but what they needed was structure and procedure to take it to the next level. I love going into a place where I can build the infrastructure and change the way the team is operating. So the structure of it, putting in the procedures and the metrics and the KPIs so that you know when you’re doing the right thing. Because if you don’t have all that, I’m not really sure how you manage a large team if you don’t have the metrics that you can look at every day and say, "Oh crap, this is working. This isn’t working." Looking at your leading and lagging indicators, all that. Then on this last round, similar story as the second one, which was growing really fast but didn’t have a true marketing team, didn’t have a CS team, didn’t have an SDR, BDR team. Everybody was doing something, and that’s kind of similar to the first one. Everybody had their hands in the cookie jar, and I’m like, "Yeah, that’s not going to work on my watch. Everyone’s going to have a specific role, and that’s what they’re going to do," because I don’t know how you measure it otherwise. It works really well in the early stages, but as you start to hit hyperscale and hypergrowth, you’ve got to have everything in a certain bucket so you can measure it. You know how I can affect change and make that better. Otherwise, it’s just too hard to do.

Callan Harrington 33:53
So if I’m hearing you correctly, to play that back, it’s we’ve got to have a process. You’ve almost taken a lot of these companies where you’ve had these situations where it’s like, "Okay, we’ve got a really good thing going here. Now, in order to get this to truly be set up for scale, we need to put some process and focus on both the sales process as well as focus in those different positions."

David Greiff 34:20
Yeah, the CS process, the marketing—just everything has to be—and maybe that’s just because of the way my brain works, I need to have it in certain buckets so that I can look at it. But I do believe you’re right. All three of those places were like, "Go build the structure and process, and the rest shall follow." I think if you get that right along with the content, it’s a hell of a lot easier to impact the change and the revenue growth that you’re looking for. Otherwise, it’s just too hard. You can’t grow your way into everybody doing everything.

Callan Harrington 34:55
Yeah, it makes total sense to me. So we’ve touched on a number of things that work right, which I think is excellent. We’ve talked a lot about what didn’t work and what we have to change in order to get there. Two questions, starting with, if you could have a conversation with the David that just jumped into sales, what would you say to him?

David Greiff 35:25
Don’t do it. No, just kidding. Find a good mentor. I tell—we’ve got some younger folks that work for me here—I like, "Constantly learn." I made them all take a Pavilion sales training. They’re all doing it. It’s super awesome because even if it doesn’t totally apply to our business, I think at the end of the day, it’s going to help them when they move on. I’m not stupid—sales reps are going to turn, leave every three, four years, whatever. I want them to go get a job at Oracle, go get a job with Microsoft or Google. You’ve got to do that if you want to be good. So learn—just be willing to read, listen. I mean, it’s so much easier now than it was when I was—I had to go read really crappy books and didn’t know if they were good or bad, didn’t have Goodreads or any of that stuff, right? I think that’s number one—make yourself better every day. Because sales, people think sales is for the social kids in college. That’s kind of bullshit. Sales is actually a science. At the end of the day, it’s a big numbers game, but you’ve got to be really good at telling the story around the numbers. But you have to always improve. That would be number one—work your ass off to improve.

Callan Harrington 36:55
That’s excellent. That kind of sums it all up, to be honest with you. When I look at some of the things you’ve talked about today, one that I think is a great takeaway is that content piece. That one is something, again, nobody—I rarely see it get talked about. You hear about ABM, right? ABM takes kind of the buzz, and it’s essentially plugging that content into an ABM process, which I know you’re a big believer in, because we’ve just worked together in the past building that structure. But I’ll tell you what—the one that I think will probably stick with me more than anything is how we can tell the story with numbers so well that if we’re not in the room, it’s telling the same story as if we were. Because that is true a lot of times, especially with board meetings, right? Even the rest of the exec team may not be in that meeting with the board—it may just be the CEO. Being able to prepare that CEO for that is a big deal, or a CEO doing a leave-behind and making sure that yours is paid. I think that’s an excellent takeaway.

David Greiff 38:00
It also applies to selling too, right? That’s going to get forwarded to 100 people on an enterprise deal—maybe not 100, but 10 people, a lot. So it still applies—the numbers apply, right?

Callan Harrington 38:13
Yeah, that’s excellent. I love it. David, thank you for hopping on.

David Greiff 38:17
Thank you, Callan. This was a ton of fun. I knew this was going to be a good one, so I’m excited for it.

Callan Harrington 38:23
Good. Well, I appreciate it. How can people find you? How can people follow you? Where do they find you?

David Greiff 38:28
Yeah, I’m on LinkedIn. I try to respond even to all the salespeople who hit me up 100 times a day on there. I try to respond to all because I do appreciate the art of selling. So LinkedIn is probably the best way. My email is david.greiff@playonsports.com.

Callan Harrington 38:47
That’s excellent. So happy to respond to anything.

David Greiff 38:51
I love it. David, thank you for coming on. This was a lot of fun. I can’t wait to get this one out there.

Callan Harrington 38:56
Cool. It was great talking with you. Thank you, David.