Transcript from REVstars interview with Ashley Grech
Speaker: Ashley Grech,
Global Head of Sales at Square
Interviewer: Sydney Sloan, CMO at SalesLoft


[Intro, musical overlay]

Ashley Grech: Hi, Sydney.

Sydney Sloan: Ashley, how are you?

Ashley Grech: Good.

Sydney Sloan: Nice to see you. Thank you for coming.

Ashley Grech: Thank you. Thanks for having me.

Sydney Sloan: It’s amazing. It’s amazing.

Ashley Grech: I am Ashley Grech and I am the global head of sales at Square. I’ve been there for about two and a half years now. And when I tell my parents what I do, not just the number, not just about driving profit and hitting a target, but I really see our team as a team of evangelists. And we take that very seriously, that responsibility. Not only to evangelize to the markets that we enter in each country, in each market that we’re in, but also we evangelize back to the company to influence product.

Sydney Sloan: What about the people themselves? So, one of the things when you think about being remembered, right, it’s for the people that you develop. And so, how do you look at and identify people with high potential?

Ashley Grech: Sometimes people come to the surface and you start seeing something that maybe even they don’t see. That’s one sort of brand of people that are really high potential, that you’re like, “That person’s special.” And over time, they might not see it yet, and you develop them and you give them projects that are a stretch. And every project thereafter is also a stretch. And just seeing them grow, and then, a year from that time or even two years from that time, being able to point back and say, “Look at the things that you’ve done.”

Sydney Sloan: You talk a little bit about your growing up and kind of your work ethic. I grew up on a farm, and so I think it just inherently had to work hard. And my dad had this bumper sticker that said, “Get it the same way I did. Work for it.” But you have a saying too, which, “Anything worth having, it should be hard to work for.” Do you remember the exact phrase?

Ashley Grech: Anything that’s good … Anything that’s worth having is hard to get.

Sydney Sloan: Why do you believe that?

Ashley Grech: I feel that way because when you see people that are really excellent at something, none of it has come easily. There’s always an element of natural talent. You see that in athletes and in professionals and whatnot. There is a natural ability factor there, but nobody skates to the finish. Nobody is the best for nothing. That’s impossible.

Sydney Sloan: When you’re in an org so big, there’s what you have direct line of sight and can touch. But then, if you’re trying to translate that down into different teams, how do you make that happen?

Ashley Grech: It’s a work in progress. I’m not going to lie. The org keeps growing and you’re like, “How are we going to do this?” But it’s about making believers of people every step of the way. And then, also, I think there’s something that needs to be said about every level of leadership also having the humility to say, “These are the things that I’m working on. I heard you. This is what you want me to work on as well.” This is my mindset about this, but if they think that their leaders are tone-deaf to the struggle, I don’t think that they can follow those leaders.

Sydney Sloan: So many people get caught up in the day-to-day of their job that it’s hard taking the time to spend outside, to network, to find those people, to stay in touch. How do you balance it?

Ashley Grech: I’m laughing because it’s really old-school, actually. The people that I really care about, they still get Christmas cards from me. They get birthday cards, handwritten. That’s my act of service and love. That’s how I show them that I’m still thinking about them. So, that’s big for me.

Sydney Sloan: Okay. If you were to pick one thing that you enjoy putting your kind of heart and soul into, what would you say that is?

Ashley Grech: One thing?

Sydney Sloan: It could be two.

Ashley Grech: I’m a notorious overachiever, in that it takes a lot of reminders from people that care about me to be like, “You cannot do all of this. That is just not a good use of your time.”

Sydney Sloan: Do you believe in perfection?

Ashley Grech: I’m a recovering perfectionist. I mean that in that I think there’s different types of perfectionists. Also, a good podcast — I’ll send it to you — on women at work, on the perils of perfectionism. And there are a couple different brands of it. Some of them include people that don’t do things because they would rather not even bother if they’re not going to be excellent at it. There’s that. There’s people that sort of procrastinate because they aren’t able to give it their full attention that they obsess and need to give it. There are those that just beat themselves up. I think anyone could see themselves in any one of these personas. One thing that really helped in terms of this recovering perfectionism business is in the past couple years I read the book The Subtle Art of Not Giving an F. And the key takeaway for me is that in order to care deeply about things and to not drive yourself crazy over it, you do have to know what matters, and therefore what matters less than that one thing that really, really matters.

Sydney Sloan: Wrap-up question.

Ashley Grech: Yeah.

Sydney Sloan: It’s a future question. You can pick any year you want, between … Where would you want to be in that year?

Ashley Grech: I don’t really care to be anywhere but where I am. I’m not the type of person to desire to be in a different place, stage, year, et cetera. We talked before about college athletics and swimming in high school and college. I’m a big believer that if you do the things and you trust that that is the right thing to do in that moment, then the next thing will come.

Sydney Sloan: Well, I appreciate very much your time, and being here and sharing your stories. And we look forward to seeing you again, wherever you pop up.

Ashley Grech: Thanks for having me.┬áIt’s always good to see you, Sydney. Thank you.