What’s it like to be the first sales employee at a fledgling startup? We wanted to find out, so we reached out to Mark Kosoglow, who was the first employee at Outreach before the company was a household name. He worked his way up to Senior Vice President of Global Sales as the company grew, and is now the Chief Revenue Officer for Catalyst Software. Mark was kind enough to sit down for an interview and tell us about his journey. (note: this interview has been edited for length and clarity).
1. First off, how did you get your start in sales? When did you know that it would be your career?
I started at seven years old. I was at my uncle's house in Delaware on a summer vacation trip, and the rumor is I didn't like the toys that he had. So I packed all the old toys his kids had played with when they were my age and went around the neighborhood trying to get people to swap with me.
My real sales career began when I was a teenager. My dad told me I had to get a job. He told me to find a job I wanted, or else he would take me to the grocery store the day after my birthday and I’d work there. So I relentlessly called a shoe store at our local mall, and eventually wore down the manager enough that she gave me an interview. I ended up getting the job.
When I went to college, I did a couple of telemarketing jobs. Later, I actually got a job at the same shoe store (it was a seven store chain in Mississippi). So I continued to sell shoes. I was the top salesperson out of all seven stores in Mississippi, even though I worked half as many hours as some of the employees. I was just unbelievably good at selling shoes. That's when I knew I was good at sales. Every sales job I did really well, so I decided it would be my career.
2. You were the first employee at Outreach. What was it like running a sales team at a fast-paced startup?
It was no different than any other job I'd had. It wasn't easier or harder. It was just different.
You know, the story goes that Manny Medina (the Outreach CEO) was my first SDR. That's completely true. He gave me about a thousand leads a week. I took those leads and put them into Outreach’s first product, which was a sequencing product that automates multiple touches over time. If they replied, we would book a meeting. And with thousands of people in the sequence, I had my weeks filled with meeting upon meeting.
I would run all of those meetings every day, and we did about a million dollars in sales in the first six months. Then I hired a sales team. I still did some of the sales, but I hired three people that I knew well and one person that was referred to me by someone I trusted. The person who was referred to me ended up being the top rep at Outreach. I think he still is one of the top reps, and probably sold more Outreach than anybody in history if you add all the sales together.
So with myself and those four SDRs, we had set a really good foundational team that knew how to get deals done. My team wasn’t really looking around for our next role or the next promotion, we were all concentrating on selling as much Outreach as we could. We had a great commission plan that rewarded us for doing that, and everyone made a lot of money.
3. What are some things you did to win deals over your competitors?
We had some built in product differentiators, and we identified what those were, and we sold their value, and we reordered buying criteria to make those super important. For example, we were the only people that had an unsubscribe link in our sequences, and we sold that to our customers in a way like, “you're gonna endanger your company if you don't have this.”
For a while we were the only company that had automation in our sequences, and everybody else was all manual. Then for a while we were the only company that had really great reply detection. We went on that like. We would find something, and then make sure that we made that really important and reordered the buying criteria, and then sold people on the value of it and why they needed it. Basically, we would create a mode of differentiation based on an innovation that we brought to the market. Competitors would see that, and in the next few months they would catch up.
Then we would release some innovation that would again create a huge gap in differentiation, and we would win at a higher rate and at a higher price point. We probably went through five or six iterations of that over eight years.
But it's still the same thing now at my current job. Every product you sell has some things it does better than other ones, and some that it does worse. Your product will have gaps that you know you're competing against, and your competitors will have gaps compared to your product that they’re competing against.
Competitive selling is really about a few things to me:
One, is your energy right? Are you trying to win a deal over a competitor? Are you trying to help somebody make a confident decision? If your energy is to help someone make a confident decision, people read that and trust you. You win the deals because they feel like you're looking out for them.
Secondly, understanding their problem best to make sure that you map your solutions, benefits, and rearrange the evaluation criteria. Their problem ends up being the most important thing to base the decision on. If it's good for the customer, you’ll win. If not, don’t just lose the deal, keep it light and friendly, and be confident they’ll come back. If they don't buy this year, they'll buy next year if you do a good job. Sales is like baseball. If you win three out of ten deals, you're a hall of famer. That's how competition works in my mind.
4. At Outreach, you were selling sales-tech to sales teams, how is selling to salespeople different from selling to non-salespeople. Is it easier or harder?
There are a couple of things about selling to salespeople:
The first thing is that they think they know all your tricks. They really don't. The things that you do, you know, the sales techniques that you use in order to help people make a good decision. You would think that they would realize what you were doing, but they don't.
The second thing is, you'd expect that you know, since they’re sellers, that they'd be more open to talking to sales.
You think they would respect call calling? They don't. I can't tell you how many times people have reamed out one of my SDRs for calling, when I know that their sales team is doing the exact same thing at the exact same time. They're reaming my team out for cold calling, but I bet you they sent an email that morning encouraging their team and telling them to make more cold calls.
In my experience, there weren't a lot of “game recognizes game” people. There are a lot of sales leaders that just really aren't that good as salespeople, and they're not like real sales professionals, and they're not students of the game.
That was the most surprising thing to me. To be honest with you, I thought that game would recognize game. Like really appreciating a great discovery call for example. Some people did realize that they were in a great sales process, and we did get complimented on that all the time. But I would have thought that it would have made a bigger difference than it did.
5. You're in leadership now. Do you ever miss being an individual contributor?
No, I sold stuff for thirteen years. I do like to be in deals, I still like to sell. But I don't want to do all the busy work of an individual contributor. I enjoy developing people, coaching, and helping people create processes. Now, I enjoy measuring and data analysis and applying fixes that help an entire team. I don't miss being an individual contributor at all, really.
And if I want to get into deals. I think I'm still a good enough seller that my team will bring me into deals. But no, if I wanted to be an individual contributor, I'd be one
6. What's your favorite sales movie?
There's a bunch of cliche ones. But I think they're all very wrong, in terms of culture, mentality, you know. I think that they actually hurt the sales profession rather than help it. I don't know if typical sales movies give you the right energy to be in the right mindset to help your customer. So I might argue there's not a good sales movie out there.
