Matt Rosenberg: Why You Should Not Hire Sales Leaders From Big Companies | E1068

If you want to find efficiency, find a mom. They will be the most efficient people on the planet. Find a parent, particularly a parent of young children. More stuff will get done in an eight-hour block than you could imagine. (instrumental music plays)

Matt, I am so excited for this. As I said to you just now, I heard so many great things from many mutual friends. So first, thank you so much for joining me today.

Well, thank you, Harry, I really appreciate you having me on. It's, it's an honor.

Now, I would love to start with a little bit of context. I want to start on entry into sales. How did you make your way into sales in the first place? Let's start there.

Yeah. So I am a little bit of an accidental sales leader. You see, um, after graduating college, I didn't know what to do, so I went and backpacked through South America. And along the way, I decided to go to law school because I figured you could always make a living as a lawyer. That is a very bad reason to go to law school, it turns out. So after graduating law school, I became a lawyer, and not a very good one at that. And it was there that I said, "I need to do something else with my life. I need to actually have impact." And so this was the late 1990s, the first dot-com boom was happening out in California. I was a lawyer in Chicago sitting in a very large office building wearing a suit in a very large, um, office, and I was lonely and my soul was dying, and I thought to myself, "Boy, if I just move out to California and join a startup, everything will take care of itself." So I remember telling my parents, "I'm moving to California. I'm gonna take a pay cut of about two-thirds, and I'm gonna join a startup." And they said, "Are you out of your mind?" And that's what I did. I moved to California, I joined a startup as the second employee, and along the way, um, you know, I joined them as their head of business development. They were raising money, I knew how to fundraise, I knew how to structure contracts, I knew how to structure core partnerships. So they hired me to be their head of BD, and along the way, we had multiple pivots. The business, like most startups, failed a number of times, and we kept pivoting our way into a new market, and I was the one that helped the company figure it out and sell the first big solution. And then I fell in love with sales. The, uh, intellectual aspect of it, the emotional aspect of it, all of it. And that's how I ended up in, in sales and as a sales leader.

Can I ask you a really personal question? I didn't expect to go here, actually. I, I actually did law as well, because I thought you could always earn a living as a, a lawyer. And I, I always wanted that security. I wanted something to fall back on. Um, I saw my grandparents lose all of our money when I was younger, and it really just instilled this fear of having nothing, and so I wanted that security of I could always have that. Why do you think you had that need for safety of, "Oh, I can always make money as a lawyer"?