top of page

Outreach VP Sales Mark Kosoglow: How to Make Your Next $100 Million

We interviewed a billion dollar tech company's first-ever sales hire. It's Mark Kosoglow, VP of Sales at Outreach!

Mark's specialty is owning the process and ensuring effective execution. Hopefully you'll come away with a trick or two about how to get to your next hundred million.



Adam Conner: Hey, Mark. How are you? Thanks so much for talking to me today.

Mark Kosoglow (00:58):

I'm doing well, Adam, nice to meet you.

Adam Conner (01:01):

I am curious to get your story because it's a bit of a full circle journey for me personally. I have been in the career world a little while and because of that, and because of my tech sales experience, I've been subject to pitches from Outreach before, but now I get to hear it straight from the source, from the person who is not only building the team, but building the sales. First, I just got to say with that groundwork, it's great to talk to you from that perspective, a perspective that you probably didn't even know.

Mark Kosoglow (01:28):

Well, listen, I appreciate it. Hopefully we did a good job.

Adam Conner (01:32):

Oh, of course you did a good job. Broadly speaking you have done as well. Outreach is absolutely exploding. You've seen that personally from the very beginning, all the way in 2014. But the first question that I want to ask goes way back before that and talk about your process a little bit and what you've learned over the years. I want to start with the foundation, which is what is the most similar between your experiences of selling Outreach today and your experiences of learning sales skills via watching videos on how to sell shoes at the mall?

Mark Kosoglow (02:07):

Well, first of all, I actually did watch 14 videos on a small black and white TV in the back of a shoe store that honestly had the worst shoe store name of all time, The Athlete's Foot.

Adam Conner (02:22):

Oh, yikes.

Mark Kosoglow (02:23):

Yeah, will never understand that one, but this is what I walked away with. I didn't know it as a young person, as a teenager, I was 16 years old doing this, is there are two ways to sell. There's probably more than that, but I'll generalize. There're ways two sell/ one way is to create demand. And the other one is merely to supply demand. And what I mean by that is you can be at a shoe store and you can stand next to the shoes. And when somebody asks you for a size, you can fill that demand, right? And there's a lot of sellers selling software, selling insurance, selling cars, you name it, that are demand and fillers. They sit around and they wait and they give the person what they think they need. I learned in those videos that I would prefer to be a demand creator. I could take somebody that brought me a shoe and said, "I need this shoe," and pause for a second and think to myself, "Is that really what they need?"

Mark Kosoglow (03:38):

And then how to evaluate that situation to determine what do they really need and then create demand around what they really need and then sell them something that was awesome. And this is strange, but in a little podunk mall in Greenville, Mississippi, I had multiple dozens of repeat customers that would only buy their shoes from me, from a dude in in a shoe store, in a mall. And that's not very common. And it really is because of what I learned in those videos is to find what people really need, create domain for that, and then help them to buy it so they can realize the value. And I think that's what I've always brought with me through my entire sales career, whether I was doing multimillion dollar deals with school districts or doing multimillion dollar deals for software.

Adam Conner (04:32):

And that notion of focusing on the needs of people you've said it's impacted your sales career, but I happen to know it's gone a lot further than that. My next question is around the way that you've built and curated teams over the years, because I know it's also been a long standing priority of yours all the way back to the mid 2000s when you decided to run for and be appointed to the Tyrone Borough Council. At the time, you said for that community, you needed to focus more intently on their needs to this place that you had come to call home and love. Now that place, that home for you, is Outreach and that community is the team. How does that bleed over from your public life into now your private sector growth?

Mark Kosoglow (05:11):

I learned a lot of lessons of being in local government, probably the most depressing of which is busy, smart people are too busy to participate in government. And there's a lot of local governments that would operate much better and their citizenry would be much happier if people actually sacrificially gave of themselves to serve their communities in that way. Beyond what your core question is just me to implore smart, busy people to give to their communities in that way. It's ultra rewarding and those institutions need you. Right now, there's a lot of people there that are doing their best. And in my experience, many of them just aren't capable of some of the things that people that are doing things in the private sector. Listen, I think that a couple of my biggest takeaways from that is you can't always do what you want to do.

Mark Kosoglow (06:17):

Sometimes there's a regulation. Sometimes there's a public opinion. Sometimes your job is to represent the people and what they want, not your own interests. And I think what I took away from that was really how do I figure out what area that I need to fill the need and how do I prioritize how to fill that need in a way that aligns to the outcome that is best for a community of people or a customer base or a specific account. And so I think that my time on Borough Council was extremely frustrating and extremely rewarding at the same time. I think that our private sector lives are very much the same way. Another big takeaway was just learning to balance those emotions. When you're being recorded and you're sitting in a public building and there're dozens of people watching you, when you let your emotions get in the way it delegitimizes the logic and the thinking that you're doing.

Mark Kosoglow (07:25):

I think in private sectors, we don't realize it's just as impactful because it's not in the same setting or it's our job versus you're serving by the grace of the people. I think that was another big takeaway is just trying my best to manage my emotions. I'm a very impulsive, emotional person. I have an immediate reaction and trying to govern that, I'm not great at it even still, but I'm more aware of my need to do it so that I can let the logical part of what I'm saying, be as effective as it needs to be. Those are a couple of takeaways from that time of my life.

Adam Conner (08:06):

And certainly balancing logic with the right amount of emotion can make for fantastic relationship building and also team building. To speak to that logic for a second, I know that you're a big fan of having efficient, scalable systems for doing things, whether that be a stack that you use to grow your outbound pipeline, whether it be all the way down to the strict routine you take, even as exact as waking up exactly at 6:38 in the morning. And I'm curious as to how that bleeds over into the way that you teach your team to build efficient systems so that they don't let their emotions get the best of them.

Mark Kosoglow (08:46):

Yeah. I am a routine, process, precision personality, and the reason is because I have to be, because I have really bad memory. And so I still remember when I became aware of what was the problem is at a house I owned. There was the exit ramp from the interstate and you drive through my town and it was about a mile and a half to my house. And right in the middle of that basically was the grocery store. And I was getting off the exit ramp, probably been driving three or four hours that day when I had a huge territory that I had to cover as a rep and my wife called me and she's like, "Mark, can you pick up some milk?" And I'm like, "Yeah, babe. No problem." And I immediately commence to drive past the grocery store and go home.

Mark Kosoglow (09:43):

And I come in and my kids are "Hi dad," and I'm giving hugs and she looks at me and she says, "Did you get the milk?" And I have this immense feeling of failure of my wife's been here all day, helping the kids, doing all this stuff. And she asked me for one thing, which was to get milk and keep that in the front of my mind for literally two minutes and act on that. And I failed and I really got upset with myself and immediately turned around, went back, got the milk. And I started Googling, how do you remember stuff? How do you become more process oriented? How do you not forget as many things? And I came across this book by David Allen called "Getting Things Done," which has its own subculture.

Mark Kosoglow (10:31):

I read the book and within three or four weeks, 70% of the stress of my life went away because as I realized that my brain was so busy holding ideas that I wasn't able to creatively have ideas. That has now rolled into the fact that I believe that you have to have a trusted system that allows you to capture the inspirations, ideas, problems, anxieties of the day, and then process them into things that you can either decide to ignore, throw away, or engage in and create projects around. The way that I talk to my team about that is listen, when you're at your best, you could be following a great process. It could be great skill. It could just be being lucky. When you're at your worst, you need something to rely on and you can't always rely on your skill, because it doesn't seem like it's there. You aren't lucky because you're at your worst, but you can always rely on doing the right thing and the best thing. You control that. People at Outreach know, I say control what you can control all the time.

Mark Kosoglow (11:42):

And partially I'm a control freak. I want more things to control because when I control it, I get to have more of a say and have more power over them. And I think that that's how I want to rep the feel is if I own my process and the individual components of it I'm doing with excellence, then it's not my fault. This is the mindset I want them to have. It's not my fault if I'm not successful. It's something else. It's my managers and my leader's job to identify that and help me get over it. Of course you want that grit, that problem solving and that getting things done, mentality and all that kind of stuff. But if I can get a rep to just say, "Listen, my job is to run the process and whether I'm doing well or poorly, I can rely on that. And it's my leader's job to help me when I'm doing poorly in doing the right things to get over the hump." I think you create these really deep, strong relationships that help people understand why you have a process driven culture.

Adam Conner (12:42):

I want to ask about one more detail on that control because even though you're a control freak, obviously, as you've said, you need to be managing an overall process. Not dilly dallying on the details. I know that when you were building Outreach towards the beginning of your tenure, you had given folks as VP of Operations, the option of either going to SF, going to Seattle, staying in State College. You gave them that flexibility. Today in a world of increasingly hybrid, remote work environments, I'd be curious to know what are some of those details that you find that sales teams and leaders tend to over control that actually doesn't help?

Mark Kosoglow (13:21):

I think that when I say control freak, I think what I mean is let's identify all the things that we can have control over and exert, our control over them, right? I think a sales leader's fundamental job is in two parts. One it's efficacy, the ability to create change. Can you get people to change their mindset, change their behavior, change their energy, change their results? As a sales leader, you got to be able to do that. The second thing is can you take somebody and help them to understand that you're going to create space for them? You back up so that they can zoom into the place that you backed up from and you keep backing up and they keep zooming in, which helps them feel like they're growing, contributing, and using their genius every day. Sales leaders should be able to create space and they should be able to make sure that they have efficacy or the ability to create change, effect change.

Mark Kosoglow (14:25):

I think that those are the two general things that sales leaders need to think about. I think that a lot of the other stuff just doesn't matter. I've just read this book by Greg McKeown called "Essentialism" and it helped me, I think, really firm up a bunch of my thoughts around this. There's process, which is how to do something. And then there's execution, which is... Process is what you do. Execution is how you do it. I think that what a sales leader's job is, is to create process and then coach to execution. I think when you start to get into how coaching works is when you start to coach to minutia, people start to tune you out. It's just overload. They can't create that level of change.

Mark Kosoglow (15:22):

I don't have any specific things. I think it's just a general mentality around if you're going to get super into the details you're probably going to get to an amount of change that no human can do. Your job is to create what to do, the process, and then coach to how to do it, the execution. That might involve a few detailed things in one conversation. It might involve a few high level mindset things in another conversation. But to think that you're going to keep your fingers on every little thing, just doesn't work.

Adam Conner (15:56):

Now, when it comes to execution, I know that Outreach is known for having amazing execution in terms of the way you operate that team. It's good that you've mentioned that because I'd like to segue into it. Can you tell me a little bit more about what that rhythm looks like for the reps that you manage and then maybe also for managers who manage them?

Mark Kosoglow (16:14):

The key for frontline sellers is you have to repeat the same message over and over again, and you only get two or three messages that you can do at a time. That's literally the key. The main reason that people don't get reps to move or they aren't successful, or their projects don't get done is because they're changing projects too often. They're not talking about them enough and they aren't focused and have just too many projects. Every quarter I pick three focuses and honestly, 80, 90% of my time is in those three areas. I try to say no to everything else. There's some stuff that creeps in and some stuff that is urgent that needs to be dealt with, but I try to make sure that as an organization though, we don't take on more than those three things.

Mark Kosoglow (17:08):

I personally try to stay aligned to that as an individual as well, right? I think that's the front line. The sales manager one, listen, man, we give reps six to 12 months to ramp. We give a manager six to 12 days to ramp. We give reps hours of coaching on discovery calls and film study and call reviews. We never talk to a sales manager about how to run a one on one or a pipeline review. We definitely don't do film studies and reviews and give them a template for how to run the call. I think what I'm finding is that the reason that sales leaders aren't effective and they aren't driving execution is because they've never been taught how to do their jobs. They've been hired and said, "Well, now you're a manager, do your job." The way they do it is the way their manager did it, mixed in with some of their own personal ideas, which may or may not be effective.

Mark Kosoglow (18:12):

I would argue many times aren't. I think if you want to get your manager level effective, you need to invest in manager enablement, just as much as rep enablement and at Outreach we have, as an example, I just got off yesterday, a call with three of our managers. They're super senior. They are unbelievable. They're great. They're crushing their number, but you know what? We had a film study on how you're doing your pipeline reviews. We listened to all of them, take reps through pipeline reviews and recorded calls to see if they were doing it the way that it needs to be done and if they were being effective in providing the rep value or not. I think that's what gets lost a lot of times is we just look at a manager and say they can or can't do their job. I think that's unfair. I think we need to say, "This is how you do your job," and make sure that we're investing in them doing that job well.

Adam Conner (19:10):

To use a phrase that you've used before to make sure that they are using the tire rather than chiseling a wheel out of a rock, am I on the right track there?

Mark Kosoglow (19:20):

That's right. Early in my sales career, I was smart enough to go sit with all the best reps and talk to them about what made them great, but I was too dumb to realize I should just copy what they did. I tried to make everything that they did great, better. I just repeated a ton of mistakes that their way they were doing things had already solved for. I remember I had a sales leader named Rene Ulloa, and he was this huge six foot six, DI offensive lineman guy, super passionate. He put his finger in my chest. He's like, "Mark, just do it how I'm telling you to do it and quit thinking about it so much." I surrendered and I was like, "Okay, man. You could eat me if you want to. You're so huge."

Mark Kosoglow (20:08):

I'll just do what you say and sure enough, I had my best year of sales ever. Then what I learned though in that year of doing things his way is I started to understand why he was doing those things. Then I started to see the real cracks where I could create efficiency. I went on to change those systems and create a whole bunch of efficiency around it, but I did it from a place of knowledge and experience, not a place of, I know better and I just heard something and I can immediately think of a better way to do it. Don't chisel a tire out of stone when you can buy one right off the rack.

Adam Conner (20:41):

I have to admit, I learned something similar. In my first year of my career doing tech sales, I was not great at my job. I thought I had a method that was going to work because that's just what I felt would work and I nearly got fired from that job. And I, at that moment took my manager, or really the leader of the sales teams, direct advice as to what exact leader to do and I just follow that. You know what? I had my best year of sales the exact year following. I went from the bottom to the top almost overnight, in a one year period. It was because of something similar and taking that advice was one of the best things I could have ever done.

Adam Conner (21:17):

As a matter of fact, it's teachings and advice, which is where I want to go with my two final questions. The first has to do with a review now of the book that launched two and a half years ago. Of course you're a co-author on "Sales Engagement: How The World's Fastest Growing Companies are Modernizing Sales Through Humanization at Scale." I'd be curious to know from that book, which listeners, you can read as well, what's your favorite teaching? Then also, what's the teaching that you think has matured the best over the two and a half years since the book's launch?

Mark Kosoglow (21:49):

Yeah. I think that one of the gists of the book is to dispel the rumor that personalization has to happen at this obscene level that creates inefficient production. What I mean by that is, I can spend all day targeting the right company, the right person, knowing that they're in a buying mind frame. I can do a ton of research and I can perfectly craft an outbound prospecting email that hits the mark 100%, that they would say this email was written by angels, right? I could write that, but you know what, if they're busy and having a bad day and behind in a couple meetings, they just delete it and it doesn't matter. I think that there's a level of personalization that has diminishing return. I think that's my favorite thing in the book is also, I think the thing that's aged the best is our job as sales leaders is to find the least amount of personalization and customization that results in the maximum outcome.

Mark Kosoglow (23:02):

That takes a little bit of experimenting and a little bit of time to figure out, but once you really that in your productivity, both in terms of inputs and outputs, increases and you really start to scale. There's a bunch of people out there that just talk about personalization, don't make cold calls and they seem to think that there's a silver bullet. Well, silver bullets only kill werewolves and most of us just need to kill regular monsters in our lives. You know what I mean?

Adam Conner (23:34):

That is a great phrase. I'm going to take that and keep it if you don't mind. Let me round out with this then, because you have taken this company from its origin to the monster, let's say, that it is today. You've taught reps how to stay on script. You've taught managers how to make sure that that execution stays topnotch and stays standardized. You've learned yourself the way of sales all the way from your teenage years to now. Through it all, I'd love to know as we close, what would be some takeaway advice for some perhaps listeners who are hoping to emulate your path to become the next Mark Kosoglow?

Mark Kosoglow (24:15):

I get asked this a lot from my own team, externally and stuff. I just want to make it pretty clear. A lot of my success is just luck. I don't know if you've read McConaughey's book "Green Lights," but McConaughey was a great actor, but he immediately got acting jobs and got great acting jobs right away. He just says, "Listen, I got lucky. I made sure that I cashed in on my luck." Sometimes it's just luck. A guy that's living in a town of 10,000 people, selling stuff to schools in central Pennsylvania should never be where I'm at today. You make your own luck. Success is where luck meets hard work, blah blah. There's some serendipity in the universe and you just got to embrace that and make sure your eyes are wide open so that when you see it, you run to it.

Mark Kosoglow (25:09):

Right. It wasn't all Mark muscling it up or Mark's so smart or whatever like that. Some of it is just, God looked down on me and threw me a bone, but I was a hungry dog and I jumped on it. Right. The second part is this, is I think that I have have two qualities that serve me really well. One, I'm very curious. I'm very curious to understand how other people think, why they think that way, why is it different than what I think? What am I thinking incorrectly? What am I thinking correctly? I don't do discovery in sales to get information to sell. I do discovery in sales to satiate my own curiosity. I think that learning how to develop a sense of curiosity I think has helped me out a ton and I think it would help people in general out a ton.

Mark Kosoglow (26:06):

The second thing is I seek to understand how I do things. When I write an email and I think it's good, I'm like, okay, how could I do this again? What is the process that got me here? The first time that I had a breakout year in my sales career, I thought it was for one thing, but when I look back and reflected on it, I figured out it was for something else. Then I doubled down on that and that thing, which I call the stink of desperation story, which I could share at some point, I'm sure it's out there, but that's what happened is I look back and I understood and I figured out what I did to get success.

Mark Kosoglow (26:47):

Then I doubled down on it. I think as a sales leader, I hope one reason that my reps would say that I have street cred is because I don't just tell them to do something. I explain to them why it works, exactly how to do it, what not to do. I give them a story about how it changed my life, a story about how it changed another rep's life, how it's helped somebody else in a deal. It's because I understand what I'm doing. It's like Steph Curry, if you ask him about his jump shot, he knows precisely exactly how to tune in and explain how to shoot a jump shot. Not that I'm on that level or anything, but I do believe that a lot of sales motions, I have my own thoughts, understanding, and level of deep knowledge around why I do it this way and how to do it. I think that those two things together have helped me a lot.

Adam Conner (27:42):

Well, for teaching us how you do it a little bit today, for throwing us a bone, I really appreciate this time to learn about your journey, your teachings. Hopefully we all picked up something here and we can go carve our own path, but for now, thank you so much for joining me, Mark.

Mark Kosoglow (27:57):

Thanks, man. Had fun.

Adam Conner (28:00):

In June 2021, Outreach closed a round of additional funding, bringing its total valuation to just under four and a half billion dollars with Mark still leading that sales charge forward, which he began seven years ago. Thanks for tuning in today. To hear more conversations just like this one, head over to wherever you get your podcasts and search Growth Culture. And while you're there, leave us a rating and review to let us know how you liked this one. To learn more about Dedicated.AI and our other events, visit us at our website by the same name, or send us an email at JL@Dedicated.AI. We'd love to hear from you about what you'd love to hear from us. Until next time, I'm your host, Adam Conner signing off.

bottom of page