Early Wins with Mark Kosoglow
Hey. I'm Vince Beese the host of the Early Wins podcast. And on this show, we interview startup founders to find the secrets of their success closing early deals and getting started. On this show, you'll learn a lot about and gain insights to closing deals, landing your first deals, finding market fit, and charting your path to scalability. Our guest on this show today is Mark Casaglala, the founder of Operator and the 1st employee at Outreach.
Vince Beese:Welcome to the show, Marc.
Mark Kosoglow:Thanks, Vince. How you doing?
Vince Beese:I'm doing well. I appreciate you coming on. You know, as I mentioned, we like to uncover a lot of the secrets early on that founders have to do or founding teams have to do to close their first deals. Being that you were the 1st employee at Outreach, which is interesting on its own, talk to us a little bit about when you're going about your business and finding opportunities, and then maybe talk about the most interesting or most significant first deal you closed while you were at the company.
Mark Kosoglow:Yeah. Well, I mean, the most interesting significant was the first one, which was one user. It's kinda funny. At the beginning of Outreach, Manny Medina, who is the CEO, was my, quote, unquote, SDR. He would send me about every Sunday a 1000 leads that he would source in a file.
Mark Kosoglow:I would put those into Outreach way back in the day when, basically, all we did was automated emails. And I'd wake up with dozens and dozens of meetings the next day. And then I would run those meetings and, you know, I literally would do meetings from, you know, 7 to 8 AM, EST to 4 or 5 PM. I go, hang out with my wife and kids and, do sports practices and all that. Put them to bed around 10, 10:30 PM, and then I would do, operational stuff inside of CRM, inside of Salesforce until about 2 AM.
Mark Kosoglow:And then did that rinse and repeat for about a year. But the first major deal we had was with a company called RJ Metrics. I think I acquired by somebody, but RJ Metrics was a a company based in Philadelphia. It was kinda like a early tableau type of thing. And their first deal was $25,000.
Mark Kosoglow:That was our first major deal. I remember our first deals were mostly one user at a time. Then we did, I remember we did a couple 3 5 user deals. But this was our first, like, significant deal. And listen.
Mark Kosoglow:I think that what ended up happening is is we met a early adopter, somebody that was really, really intelligent, somebody that was really trying to push the edge, break out of the mold, do something differently knowing that different and unique is his own competitive advantage. And when he saw what we could do, he had been trying to do something like that manually inside of his own company. Our technology operate automated all of that, and they were an awesome customer for, you know, 2, 3 years until
Vince Beese:until they And remind us, what what what year is this we're talking about? This is 2015. So at that point, there was a lot of competition. Right? You had pretty stiff competition by that point, didn't you?
Mark Kosoglow:At that point, SalesLoft had just started to release. They pivoted from a product that, scraped LinkedIn, and they gotten in trouble. So they were moving over into our space. There were a couple other kind of Neanderthal Neanderthal type of companies like Yesware and ToutApp that weren't they didn't understand sequencing, but we're doing templates and inbox management and stuff like that. And, and ToutApp had just raised a $16,000,000 round from Andreessen Horowitz.
Mark Kosoglow:So, they they were they were charging hard in this space. But, we had a technical advantage with our product in that we had the sequences and nobody else had anything like that. And so we had a real differentiation.
Vince Beese:So I imagine obviously because your product was differentiated, you went right to it. Meaning, your value proposition was, let's get them and let's show them this technology that's probably different than anything they've ever seen.
Mark Kosoglow:Yeah. I mean, I think that's what my hope was. I would say that the majority of my conversations were, isn't this just Salesforce? And which, you know, I think that that was a knee jerk reaction, you know, something that somebody would say just out of hat, because at first blush maybe you saw a list of accounts or a list of prospects and and thought CRM and there wasn't really anything else out there at the time that was doing what we were doing. So it took a lot of storytelling and doing what I'm doing in operator right now, which is let me explain to you the state the current state.
Mark Kosoglow:If you agree that the current state is broken, then the way that we operate in the current state must also be broken. And therefore, there needs to be a new way. And then I would introduce that new way as, as Outreach.
Vince Beese:And at what point so I assume you joined. You were the only salesperson there. Is that right?
Mark Kosoglow:It's just me and the 4 cofounders. That was it.
Vince Beese:Right. So when you you and the founding team are are closing these, when did you when did you sit down and say, hey, guys, there's a there there. We're really having some momentum here. What was the recap moment for you all that we really need to start scaling this thing?
Mark Kosoglow:Well, the way that we did sign ups in the beginning at Outreach was it was a lot of one call closes. I would get on for half an hour, do a really horrible demo, but I would show a bunch of stuff and tell a bunch of stories, and I think it was enough for people to get it. Then what I would do is we had a company called Recurly that helped manage our packages and recurring payments. I would literally be like, do you wanna try it? And they'd be like, yes.
Mark Kosoglow:I'd be like, alright. Well, give me your credit card. Shouldn't have done that, but give me your credit card, and I will put it into Recurly, and you have 30 days to use the product for free. If you don't cancel, then we charge your card, for the full year. So, all of a sudden, I was signing up 5, 6, 7 people per day onto that kind of a plan.
Mark Kosoglow:I mean, we did we went from, 0 to a $1,000,000. I started in, say, like, really selling in, like, August or September of 2014. By March of 2015, we'd hit about $1,000,000. And, it was all kind of, like, nickeled and dimed like that. And then we started to press up.
Mark Kosoglow:I mean, in the beginning, Vince, we didn't even have, like, an MSA or legal documents. We just took somebody's credit card and put them in a platform, and that was it.
Vince Beese:That sounds about right. What was your first big RJ Metrics was your first big enterprise customer?
Mark Kosoglow:That's our first big, you know,
Vince Beese:multiples of power. Revenue customer though? Like, what a significant deal. This is probably fast forwarding a little bit, but what what it who was that and how big was that deal?
Mark Kosoglow:I don't even remember, man. We had 3 very early important deals. 1 was with AdRoll. They had a very discriminating rev ops person that helped us a ton with, like, what we needed to build on platform to be ready for bigger companies. Secondly, we signed Adobe, and we got a huge part of Adobe using Outreach and really pitched them on the idea, and the vision and and got some immediate really good success.
Mark Kosoglow:The last big one was, CenturyLink. We signed a $1,000,000 deal with them that really helped us start to scale. And I think CenturyLink happened in maybe 2016. Oh,
Vince Beese:yeah. Pretty fast.
Mark Kosoglow:Yeah. Yeah. But we start we started we had started to do multiple, you know, 20 to 40, 50, 60 k deals per quarter, like, within within a year.
Vince Beese:And then at the time that you exited the company, how big was the sales organization when you were SVP of Global Sales?
Mark Kosoglow:Maybe a 180 reps and managers and VPs and all that stuff.
Vince Beese:And along the way, what are the things that you tried that worked and the things you tried that failed in the experimentation of sales and doing different things? I don't
Mark Kosoglow:know, man. That's a big that's a huge question. I feel like I'd screw something up every single day. Do you have, like, do you have, like, a more specific area that you want me to explore?
Vince Beese:Well, what was one thing during your your time period there because you were there for a good amount of time, where it might have been a pivot or a change in process or whatever it might have been that really helped drive up up, growth or or scale for you guys?
Mark Kosoglow:Yeah. I would say early on, there was a transition that happened from pitching to consultative sales. You know, when we probably got to 3 or $4,000,000, like, doing a lot of pitching, I had 3 AEs or 4 AEs. 3 of them kind of worked like that upper s and b, mid market, and all those type of deals. And I had a transactional person, and the transactional person was just slinging like I had the entire time.
Mark Kosoglow:He moved up the chain. He's actually still at Outreach. He was has been the number one rep several times in his tenure there. Unbelievable seller. But we we moved to a more consultative, like, discovery challenge driven.
Mark Kosoglow:What what is the business initiative that we need to align to methodology and and just really got way more sophisticated in in how we were positioning the product. Yeah. Rather than just saying, oh, look at this cool stuff we do. We started to really connect it to the problem. Yeah.
Mark Kosoglow:Kind of generic generic, but, you know, listen. Founder led sales and early sellers, a lot of them I encounter, they just vision pitch. And you either buy the vision or you don't. And if you do, you're great. If you don't, whatever.
Mark Kosoglow:You come back later, but maybe it's not for you. But at some point, you have to turn the corner to a more traditional consultative sales motion. And if you don't make that transition, then you're gonna wonder why as a founder, nobody else can sell it like you do.
Vince Beese:And that's because
Mark Kosoglow:a founder can say and sell things in a way because they have a lot more knowledge than, than the first sellers do. And so it's just, you can't replicate that. And you don't want
Vince Beese:to do it. That was an excellent response to the last question I was gonna ask you, which is what's one piece of advice you'd give to a founder who's selling today? But that that transition, I think, really resonates with anyone that's doing founder led sales today. It's like, you're right. Founder power.
Vince Beese:Right? You can go out there and sell just about anything with your vision and passion, but at some point, that doesn't work. And it certainly doesn't work for the sales organization, for sure. Right?
Mark Kosoglow:Well, that that the number one bit of it, advice I give founders trying to hire their 1st sales hire is you have to clearly define what you want that sales hire to be because otherwise, lines get blurred. So either gonna hire a rep that you will manage, teach, train, and knows what they're doing. You're gonna hire a future leader who's probably not necessarily done sales in a while, but they still have the ability to do it, and they can build out the org as they're selling themselves. And then lastly is you want, like, a GTM cofounder, somebody that's all up in the business. And for me, Manny was very clear on what my role was at Outreach.
Mark Kosoglow:I was the leader now. I I'm lucky I can sell very well too. And my job was to come in and get some initial traction, and then he gave me the VP of sales job. And then I ran sales up to about $230,000,000 with that org. And, you know, really having my I wasn't in the investor meetings a lot.
Mark Kosoglow:I wasn't in product meetings a lot. My job was to be the sales and revenue leader. Of course, I was given feedback, and there was crosstalk and all that stuff. But my role is really well defined. Now they didn't sit there and was like, why am I not at this board meeting?
Mark Kosoglow:I never thought about that because my job wasn't to go to board meetings. My job was to create revenue.
Vince Beese:Well, it's great you had a founder who was very clear on that. Right? Because sometimes when that's that clear, someone gets upset by not being invited to one of those meetings. Right?
Mark Kosoglow:That's right.
Vince Beese:Hey, Mark. Let's leave it there, man. I think this is extremely informative for our audience. And I wanna, again, thank you for coming on Early Wins.
Mark Kosoglow:Happy to help, man.
