Brendon Cassidy: Why You Should Never Hire Someone You Do Not Know in Your First Five Hires | E1124

Ultimately, what AI does is probably get- put the SDR function back under marketing. For my first five sales hires, I would never hire somebody out of network. I can tell you, no great VP of sales is ever gonna take a job with a company that's dependent on an outbound go-to-market model. That's just... nope. (upbeat music)

Brandon, I am so excited for this. I've wanted to make it happen for a while. It's been a while since we last chatted, so thank you so much for joining me today.

Also, uh, great to be here. Yeah, I think it was, uh... Last time we saw each other was maybe in Napa, like, some years ago, I think, um, f- for, like, a SaaStr retreat. So yeah, it's great to see you.

Brandon, I was young back then, but I wanna start with a little on you, just a context check.

You still, you still look good. Trust me. So... (laughs)

Dude, I, I look like fricking Benjamin Button. But tell me, how did, how did you first make your way into the world of sales, and when did you realize you loved sales?

I was sort of coming into the tech world, uh, around, like, ni- 1999, 2000, was the beginning of my career, which is hard to believe I've actually been around that long. I started my career as a recruiter. So this is before the dot-com bubble burst, which there's not a lot of people that have that as a reference point today. I was a recruiter. We worked with venture-backed companies, sort of around sort of helping them build their leadership and management teams. That was really my first job out of college. Came in at sort of the height of it, and then the entire market collapsed. And then recruiting became literally the first thing, you know... That's the first... Oh, recruiting fees? Yeah, that's just... Yeah, that's not e- There's not... That's a five-second discussion. And so that became, like, you know, an incredible career experience because it was like, "Survive. Okay, how do we survive doing this?" Because no one needs it. Certainly, nobody wants to pay for it. Everyone's firing people. No one's hiring people. Um, what now? Um, and so that forced all of us... We were all really young, and a lot of people, um, sort of didn't make it. Uh, but the- those of us that did, um, it's, you know... I d- I can't ima- You know, it's so foundational in my career, um, that it's... You know, I can't imagine not having gone through it.

What did you take away from it, that really shit hard time? How did it impact your mindset?

Yeah, I mean, we, we didn't really... We weren't really that experienced, so we had to... I mean, this might sound bad. We had to basically invent versions of ourselves that were real, and we had to convince people that those were real, that we had a level of experience and knowledge and expertise that we didn't really have, but we had to convince everyone that we did have. And that, that's a pretty good primer to get into sales, right, where it's like, you know, like, um, y- you are constantly having to kind of reinvent yourself. You have to be able to be, uh, very adaptable to who, whoever you're talking to, whomever the customer is. And that's something that we had no choice but to, to l- to learn to be that. It was be that or be gone. And so, you know, we were these 24, 25-year-old kids, you know, a lot of them from New York. I was from here, in the Bay Area, but, um, convincing people with, you know, 20, 25 years of experience that we had... We knew things that were, um, uncommon. Um, and, you know, that's... Yeah. It was pretty great experience. And every single one of the people that were there, they've all gone on to, like, incredible success, because nothing will ever be harder than that.