Mark Roberge: The Framework for How Startups Should Scale into the Enterprise -Stage 2 Capital|E1176

I was consulting to HubSpot when it was, like, one or two people and eventually joined the company as the fourth employee. The skill necessary to get a million dollar deal done, there's so much in there in terms of, like, how do I identify and build a good champion? How do I understand the political dynamics? How do I differentiate between an economic buyer, a technical buyer, an end user, a coach, and a champion? How do I, like, deal with procurement? How do I deal with legal? My million dollar seller that sells to healthcare has all those skills.

Ready to go? (instrumental music plays) Mark, I am so excited for this. I just mentioned, I've loved your content for a while now, so this is really exciting. Thank you so much for joining me today.

Oh, yeah, sure, Harry. I'm honored. Thank you for saying that.

Now, I would love to start, how did you first make your way into the world of sales, and when did you know that, like, sales was really one of your loves?

It was a- a lot, like a lot of the wins in my career, it was completely serendipitous, uh, almost accidental. (laughs) Um, you know, I was, uh, at 23, I discovered that I wanted to be an entrepreneur. And even to this day, I kinda consider myself more of an entrepreneur than a sales leader. Even though I was a founder CEO coming out of school, I knew I wanted a functional alignment and I was torn between marketing and sales. I was like, I really, like, there's not a lot of MBAs that go into sales, so that's weird, but I really love the art of the deal and I know generally speaking in tech, salespeople make more than marketers and I had a young family and, like, I was the financial, you know, f- you know, re- responsible for that, so, like, that was important and an ingredient. But I felt like the MBA provided you more for marketing. Marketing was going more in a data-driven direction. I was consulting to HubSpot when it was, like, one or two people and eventually joined the company as the fourth employee, and that's where it serendipitously kicked in 'cause Halligan was the co-founder and he is a sales guy, you know? And he was like, "If we're gonna use you one day a week to consult, then I want you to sell." And so that's how I got into sales. Like, I didn't, I was like, "All right, cool. Like, Dharmesh hired me for one day a week, you're now the CEO, if you want me to sell, I'll sell. If you want me to write code, I'll write code." Like, 'cause (laughs) it- it is what it is. So that's how I got into it and it would actually, worked out beautifully because I was not only in sales, but I was selling cutting edge marketing software. So I- I got to learn all about both, which was completely accidental, but awesome.