“The Most Unique Stories in Tech Unicorns” – with Mark Kosoglow

In honor of our 50th episode, RevOps Therapist and founder and CEO of Greaser Consulting, Jordan Greaser, connects with one of his mentors, the man who hired him at Outreach and started his career in the trajectory that led to him to where he is today - Mark Kosoglow CRO at Catalyst Software.
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Show notes

In honor of our 50th episode, RevOps Therapist and founder and CEO of Greaser Consulting, Jordan Greaser, connects with one of his mentors, the man who hired him at Outreach and started his career in the trajectory that led to him to where he is today:

Mark Kosoglow, former Senior Vice President of Global Sales at Outreach, now CRO at Catalyst Software had a “1 in 10 billion” chance, coming from a small town in central Pennsylvania, to become employee #1 at Outreach.

He shares his journey and the attributes that he looks for when hiring and what makes someone successful, regardless of where they’re from.

Listen in to hear Mark’s story as he shares insights that led him to success.

We’d also like to extend our sincerest thanks to Mark for the impact that he’s had on our fearless leader, Jordan. None of us would be here without him.

Jordan  00:00

Hi everyone, this is Jordan, the owner and CEO of Greaser Consulting. On this episode, we got Mark Kosoglow with us. Listen, this is our 50th Episode. I actually brought him on in a lot of ways just to say thanks, super busy dude. So this one’s quick; we asked a couple questions, a little bit about learning and how he got to where he got to. And then, quite frankly, just kind of me saying thanks to the guy. I’ve appreciated what he’s done for me and my career. And listen, I hope you enjoy it. And I also hope that you’ve got different mentors and folks in your life that, you know, you can just get an opportunity to stop and say thanks to so, without further ado, here’s a real quick one with Mark and I.

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Jordan  00:58

Hey crew, this is Jordan, we got Mark with us. Mark, introduce yourself.

Mark  01:03

What’s up Greaser? Mark Kosoglow, sales guy, Central Pennsylvania, husband, dad, sales nerd.

Jordan  01:12

And well, you got the nerd part down. That’s for sure. So you said something interesting in there: Central Pennsylvania. And, you know, obviously you were, you were the first employee at Outreach. Is that right? Like you were, you are number one, or you are number two; what was the number?

Mark  01:30

I was number one employee. Yep.

Jordan  01:33

Number one. So how does the number one employee at Outreach, who led all of sales and all of this come from or live now or come from Central Pennsylvania? Like how does that happen?

Mark  01:44

Like a one in 10 billion miracle. That’s how. Yeah, it’s kind of weird, man. You know, I thought about, about this the other day. I used to sell stuff to schools or run a team that sold stuff to schools and that required me going from flagpole to flagpole, is what we used to say, and so it was nothing for me, especially in central Pennsylvania. And some of my region when I worked at the one place was even more rural than central Pennsylvania is; I would drive in like three or four hours a day was nothing. And I this was back in the time where there was maybe like 200 podcasts on Apple podcasts. It was like, nothing like it was today. And do you remember that little iPod Shuffle that looked like a pack of gum? Yeah, yeah, that’s what I had. And I would, I could load like 10 or 12 podcasts up, I think, because I had the cheapest one. And I would listen to podcasts, and all those podcasts were about technology and like startups, and I listened to This Week in Startups with Jason Calacanis, and This Week in Tech and MacBreak Weekly with Leo Laporte and all those guys, and I just learned all about tech and because that’s what I was super interested in; I was like, you know, build out all these automations and things to make my job easier. And all of that was kind of like preparing me for when I met Manny Medina, which I got introduced to him from somebody I helped out with some sales advice, then Izzy Gewirtzman and oh Izzy invited or introduced me to Manny, and Manny and I became buddies and, and then Manny’s like, can… and I said, “Why am I not selling Outreach?” And he said, “we can’t afford you.” So I did the 100% commission thing, but like, that’s the long and short is I, I wrote a blog post that a dude read that was doing a Google search for something like what Outreach was doing that found Outreach on page 25 of the Google search that called Manny directly, figured out how to get in touch with him, had a few conversations with him, connected me to him, and then I was just like, when I saw the product the first time I was like, “this is the future” so I, I quit my job and worked for him on 100% commission and you know, did about a million bucks in sales in six months then boom, we’re off to the races, started hiring people, and you came on board, changed my life.

Jordan  04:11

It’s funny, though, you mentioning Izzy, like, I still talk to him from time to time. He’s still on page 25 of Google just so you know. He’s still hanging out, out there.

Mark  04:25

Deep Search is what he’s after.

Jordan  04:29

Yeah, he’s a character. But in all sincerity there you like you do 100% commission; I get that. But how, like, how do you convince a startup out of Seattle that we’re gonna have a sales office in Pennsylvania because like, that’s not a, that’s one of the most unique stories in tech unicorns. Is that blue collar USA here, like that’s where the sales office started was the middle of nowhere. How like, how do you convince people of that?

Mark  05:00

Ah, I think that I had earned enough street cred with Manny. And by closing deals, by doing what I’d say I do, you know, our buddy Theron was a part of all that stuff in the beginning, and Theron was, was good and had worked for me. And I think Manny was just like, “listen, Mark, just make, like, whatever you want to do, you can do just make it work.” And I always knew that, like, the people I hired in central Pennsylvania and other rural areas were just as capable and intelligent as anybody else. They just didn’t have the same access to opportunity. And so you know, I remember, we hired Brittany. In Brittany’s first three weeks, we’re doing work in my daughter’s bedroom, in a tiny little town. And she turned out to be an unbelievable SDR, moved to Seattle, worked at Amazon and a million other startups and crushed it and is still crushing life. And that was the norm is is like we just hired hardworking people that were coachable, that gave a crap. And we gave them the skills and the tools and the training they needed and the encouragement they needed to, to be great. I think that’s what most people need; I don’t think that they need to live in a city to have those attributes.

Jordan  06:17

Is that something though, like, obviously, where you hire and where you look today, like it’s not like you’re pinpointing Central Pennsylvania today or someplace in Kansas? But is there certain things that when you think about just getting something off the ground? Like, these are my people that you’re like, you’re really trying to find?

Mark  06:37

Yeah, I mean, you know me, man, I got my, my three attributes that matter to me. One is, are you gonna give effort? Do you have work ethic like, you know, if you had to do 100 calls a day, Jordan, and you are at call 93. And it was 5pm, you’re making the last seven calls. And like, that’s work ethic and what matters. And so I think that that’s, that’s the first thing. The second thing is curiosity. You know, you have to have internal curiosity; how does my business work? Why we position like that? Why does the product work like that? How does this… how do you do this? You have to have external curiosity, which is why did that person have that problem? Why did they try to solve it that way? Why did that solution not work? And then the last piece is you have to have, you have to connect what you learn through your internal curiosity with what you’ve learned through your external curiosity, and make that connection. And I always tell people, like, I think people have lost the ability to make a connection. If I… if you tell me it’s hot, and I say, “Well, I got a fan.” People don’t connect that the fan makes you cool. And it’s the solution to the hot; you have to do that for them explicitly and concisely. And so if you can, if you give me effort, if you are internal, or and you have curiosity, and you have the ability to make connections of what you’re learning internally and externally, then I think that you have an amazing sales career.

Jordan  07:58

Talking about an amazing sales career, like you obviously, started at 100% commission. And then I don’t know, I don’t know if you can even share, like, what Outreach was at in revenue by the time you were all said and done, but right, unicorn status, okay? As a, as like a person who goes from 100% commission sales to running an SDR shop, to all this, like hiring AEs, getting SDRs, putting leaders in place, and then the next thing you know, you’re in charge of all of sales. And then this thing goes all the way to unicorn? Like, how do you? How do you continue to learn at a rate where you can tackle each one of those stages? Because typically, in a startup, right, like, the big vision with everybody is, hey, you’re gonna make it, come on, let’s get this thing IPO. And there’s like, 20 people, right? By the time you’re at 100 people, it’s a different company, than when it was at one at 20 and a million other iterations in between. And so the types of skills and things that it takes just change from each stage that you’re at. And it’s a little bit, you know, hard to fathom that someone could start as like the commission salesperson to running the whole thing at this, like really high octane place. So like, how do you? How do you conquer each one of those steps?

Mark  09:21

Well, you know, first of all, I wasn’t opposed to taking a step back. I mean, I was leading a sales team that was responsible for like $15 million dollars in revenue and hundreds and hundreds of customers. And I had reps on the East Coast to the West Coast. And I, you know, that was, I took a step back and started selling again. So that’s the first thing: take a step back to take 10 steps forward, you know, especially if you keep walking half a step forward, and every time you keep bumping your head, maybe it’s time to take a step back, take a different direction, so you can walk a little bit faster. So that was the first thing; the second thing is, is like I don’t know, if there’s a right way, Greaser. I think that there’s a way and that commitment to that way will usually end up in success. I think the problem that most people have is that they keep changing their ways. And so they never, nothing ever gets a chance to stick. And you know me, dude. You’ve known me for, I don’t know, how long have we known each other, probably 15 years? All together.

Jordan  10:27

The irony is, and I gotta digress for a second. Yeah, first time I met you, you were in front of an audience of like, eight people. And I don’t even know what the tool was, but you were like, and I was, I think, 13. I was watching you talk about how you had automated your whole job to a point where you only work two hours a day, and it’s super simple. And you just clicked. I was just like, “I have no idea what this guy is talking about. I have no idea why it matters.” But it was just funny, because at the beginning, you were talking about how you had worked with his job, and you learn how to automate a bunch of stuff. I remember you talking about like, the early stages of that. But anyway, I’m digressing.

Mark  11:06

Well, and you know, we used to, we used to play basketball against each other, back in the day, too. So we go way back. But I think that, you know, you’ve known me long enough, we’ve worked together for seven or eight years, or, you know, sort of together, and I say the same stuff all the time. There’s just stuff I believe in. And like, I don’t know if it actually is the best way or even the right way. But it works because I’m dedicated to it. And I sell people on it, and I get people to do it. And I think just getting people to do something is like half the battle. So you know, like, what are all the things you need to learn along the way and all that kind of stuff? If you’re like, listening and talking to your people, and you know, got a couple people in it, that you’re that are mentoring you and that you can go bounce stuff off of that’s not everybody’s quite ready to process yet. You end up you know, I think with a really strong catalog of stuff that you can pull from, and as long as you believe in it, and work it really hard, it’s good. And so there’s that. And then the second part is, is like do you have like this experiment mindset? Like everything I do is an experiment; I just watched to see if it works. If it doesn’t work, I try something else. If it does work, I pour more fuel, fuel on the fire. But I think, don’t and don’t abandon stuff that’s working for something that you think is going to work better super easy. Working is great. Working better is sometimes that’s… I think Pat Riley calls out the disease of more. Sometimes you just get… you make yourself sick trying to get more and more and more; sometimes what you got is good enough.

Jordan  12:52

Well, that actually makes me think about the early days in that Central PA office where like we were humming, but not like, not fantastic, but we were humming enough. If you remember, like we had, we had changed, like literally everything about the way we were reaching out. And like six weeks later, there was no pipe, nothing being generated. And it was like, “What in the world just happened?” Right? Because it was like we were trying to get fancy; we were trying to try to use LinkedIn best practice, right? And all this kind of stuff. And it was like, “Nope, we’re just going back to what works. And we’re gonna pour gas on it.” And you know, I always joke about this, we rode the same sequences from 3 million to almost 30 million.

Mark  13:39

100 million, dude, because it doesn’t matter. People: Oh, is it Hey, or Hi? Don’t matter. Oh, should you do your value prop first or this? Doesn’t matter, like doing something matters, and then just watching to see if it works. You know. I will say though, that like different industries are different. When I moved to my new job at Catalyst. The aggressive approach did not work that I was used to when I was selling to sales professionals. But we saw it early. One of my SDRs was like “Yo man I’m getting a lot of unsubscribes.” We went and looked; oh my god, we get way too many unsubscribes. So guess what, we turned that sequence off, toned it down a little bit, and did another one. And that one’s working great. It has like a 14 or 15% reply rate with 1000s of people going through it. And so that’s, you know, it’s not that much different. It just was… took a little bit of a tweak, but like, we were watching it for big stuff that could have gone wrong when we saw something went wrong. But yeah, I bet you the sequence I’m using now isn’t that different than what I used to grow Outreach.

Jordan  14:41

I actually thought… you and I had a conversation a while ago about how there’s just some different folks now that are putting all this information out there and it’s like they came up with it like, it’s like, “well, no, you didn’t; this person did. No, you didn’t; this person did.” And I was, I was thinking about that. And I was thinking like I actually walked out of that conversation I was like, “Well, I can think of three things that are like huge on LinkedIn right now that I created that like I’m not getting credit for.” But I thought, “You know what, like, to be honest with you, and I had to like kind of look at myself like, those three things that quote-unquote, I created. Like, somebody else actually talked about it first; somebody else iterated a little bit on it; I probably tweaked it a little bit. Like none of that stuff actually came out of a vacuum.” Sure, right. And there’s, there’s a whole lot more of just early conversation that ended up becoming something that like, I probably shouldn’t get credit for either. You know what I mean? Like, that’s the fun part about working on a team though of like, you beat on it, I beat on it, you try? Sure. You might be the person who finally came up with the idea. Right? But like, guaranteed, there was a lot of conversations in between to get there.

Mark  15:49

Yeah, right. Shoot, I just claimed stuff now. I’m old enough, I can just do it. I just say I came up with most of everything we did. Makes my story better. So I’m, I’m, I’m all about the story.

Jordan  16:02

Yeah, I could tell that Mark. Right? It’s all about you.

Mark  16:05

But I do, I do remember when we almost sunk the company. Because there’s some kind of… we hired somebody. We got mis… There was some kind of miscommunication when he was leaving about an experiment that he wanted to run that everybody thought he… we were actually going to do; we moved to that. And it did totally kill the pipeline. And you and your buddy, Alex Lynn, saved the company. No joke. They won Outreachers of the Year for how they turned around the company because of the… or turned around the pipeline. Because it were, we were, we were sucking wind for a couple months there because of that mistake.

Jordan  16:39

Yeah, I tell people about that. And the irony is, is like that whole change of process was conceived in, on one Saturday and Sunday. That was that. And that’s like, that was the whole thing it was built on to your point to 30, and so on, and all these different things. But I know Mark, you actually have a pretty short window today. And so we weren’t able to talk long. But I wanted to bring you on today because this was our 50th podcast episode. And the reality is, I really wanted to bring you on to just to say thanks, because I wouldn’t be here running a consulting company without… I still remember the first interview with you. This is this was like early Outreach interviews, I sit down and I’m in this like, weird place where, you know, Mike’s out there kicking a football with no shoes on, running down the hallway. Alex is wearing his like, like basketball jersey clicking like on LinkedIn. And I’m like, “What are you doing?” He’s like, “I don’t know. They just told me to do it.” Right? And I’m like, “What is this place?” So I sat down with an interview with you and interview with you was like, “well, Theron says, you’re good. I don’t really remember you that much. But if Theron says you’re good, I’m good. Can you give this job 110%?” And I’m like “I don’t know, I don’t know what the job is.” And you’re like, “Well, can you give 110%?” Like, I don’t know. But anyway, without, without that conversation, that introduction, you know, we wouldn’t be sitting here on this side, shooting the breeze and having a podcast about it. So, in some ways, this episode is in honor of you, Mr. Kosoglow. Thanks for bringing me on. Thanks for having me on back in the day.

Mark  18:11

Well, that’s super cool, man. I appreciate that. But listen, you know, I wouldn’t be here without you and all the stuff you did too. So we helped each other that’s for sure.

Jordan  18:20

Alright, man, well, look, we’re gonna cut it short. This was a real fast one. Because again, I know you I know you got to run, but I appreciate you coming on and thanks for everything that you’ve done in my life. And, you know, good luck at Catalyst as you continue to build and grow. And, you know, keep making it happen. Keep crillin’ it.

Mark  18:38

Gotta seat for you when you’re ready, buddy. 

Jordan  18:42

See ya, Mark.


Hot dog. That was a great episode. Thanks for listening. If you want to learn more about Greaser Consulting or any information you heard on today’s episode, visit us online at www.greaserconsulting.com. Be sure to click the Follow button and the bell icon to be notified on the latest here at RevOps Therapy. Thanks and see you real soon.

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