Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241

Founders definitely should not create the playbook, but I think founders wait too long to hire a go-to-market. And I think they do that because they feel like they can't hire a good salesperson, potentially without a bunch of traction. The big mistake that people make, as they transition to the next phase, is people don't increase price into a point where they find friction.

Ready to go? (upbeat music) Matt, I'm excited for this, dude. I've heard so many good things, both from Ashley and from Parker. So thank you so much for joining me today, man.

Yeah, absolutely. Thanks for having me. I, uh, likewise have- have, uh, heard a lot of great things and watched a lot of great episodes on the podcast, so excited to join you.

Yeah. Bribery goes a long way, dude. Uh, listen, I think there's a moment when people fall in love with sales. Can you take me to, when did you fall in love with sales and realize that this was the career for you?

You know, candidly, I've been, uh, I think in love with sales since I was, you know, selling wrapping paper in fifth grade in elementary school. And I think for me, uh, it's always come from probably some part of competition, you know, wanting to, uh, to sell stuff and- and kind of be number one on whatever leaderboard it was. And believe it or not, that's- they get you primed for that in elementary school when you're selling wrapping paper or discount codes to your local stores or whatever. But then all the way through college, I was selling hot tubs and appliances at Sears and Cutco knives and really anything you could- you could think of that was a commission job. Uh, I was doing it from a pretty young age.

Do you think that people are born salespeople or do you think it's something that can be learned?

I think there's a lot of people that are born that could be salespeople. Um, you know, just given the- the kind of the attitude that you have. And I think there's certainly some people who are born who probably don't, you know, would like run in the opposite direction from any sales job. But, uh, I think it comes from, you know, wanting to be, uh, you know, wanting to be competitive and being okay when you lose, because in sales, like yes, of course you win, but you lose the majority of the time really. And so I think there's a- there's a lot of dynamics, uh, that I think are, uh, that you have to kind of have the ing- the right ingredients. But I think from there you can certainly, you know, teach a lot of the skills that, you know, that- that make a good salesperson good.

Do you think it's okay to be good with losing? Like, I fucking hate losing. I would- I would kill my kids if they ever said that they were okay to lose. It should hurt every time, in every way, and you should remember it so you never feel it again.