The Pavilion Podcast
The Pavilion Podcast

Episode · 1 year ago

Ep 49: Creating Discomfort w/ Ashley Grech

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Ep 49: Creating Discomfort w/ Ashley Grech

Hello, everyone. And welcome back to the revenue collected podcast. I am your host, Brandon Martin, and you're listening to Is this a good time? The show where I asked revenue collected members some really basic questions, and they have incredible answers in a short, 15 minute conversation will be coming to you live Tuesdays and Thursdays each week. So smash that subscribe button so you don't miss an opportunity to learn from members of the RC community, any of which, especially this one today. Who could be your future boss? Our guest today manages 400 people. So maybe she is your boss, Ashley Greg, the global head of sales at square. And we talk about why you might want to start making prospects have been uncomfortable before we get going with the questions I want to tell you a little bit about this month Sponsor. It's six cents six cents. The number one account engagement platform helps you to identify accounts that are in market for your solution. Prioritize your efforts, engage buyers the right way with highly relevant messaging and measure what actually matters with the six cents platform, you're able to get into more deals, improve win rates increase overall pipeline and optimized budget spent. To learn more. Visit six cents dot com slash revenue collected. All right, let's do this. Episode nine Is this a good time to? All right, we are here with Ashley Grech. She's a global head of sales of square and, uh, somebody who I consider a good friend. And I'm so glad to be here with you today. And, uh, and have you on the revenue collected podcasts. Thank you, Brian. I hope you can hear me smiling, because I have. So I've so enjoyed our friendship this year, especially as the economy is in a bit of a spin. Um, it's been It's been great. Thank you. Awesome. Awesome. Well, I'm not going to take it easy on my all my hardball questions anyway. Okay. Um, you know, uh, you know, as everyone who listens knows, you know, we're gonna just get to know Ashley and learn about her and her career. So bring us through that I mean this, you know, it's not...

...overstating it to say that you are in a tremendously large position in a publicly traded company that has got to be one of the hottest tech companies of the past, you know, a couple of decades with perhaps one of the best leaders, you know, people put Jack Dorsey up with with the titans of the startup world. So give us a sense of how you got here. Like, Wow, Well, thank you for that intro. How do I even live up to that? As you said before And the global head of sales, That's where I feel immensely lucky every day. And I think that's pretty pretty great. Feeling lucky and excited, I oversee a team of now about 400 or so reps, uh, in five countries, soon to be many more countries, soon to be many more reps. As you know, the opportunity is there. Businesses need better and streamlined, more cost effective technology to get them through this time and that which combines technologies. And so I'm excited to have our team deliver that. How did I get here? I started my career in traditional financial services, and to be honest, I I really appreciated it. I never in my life was like I'm gonna be a banker like nobody says that I think very few people also grew up in there like I'm gonna be in sales. But sure enough, I went into I went into banking because truth be told us, because it's an excellent company. Went to J. P. Morgan and they were willing to pay for my business school degree. So I was like, I'm out of there after that. And then I stayed for 13 years, so I mean, that's a testament to like a place where you can really grow. I held a number of roles there, though one was like a strategy based role. And then after that, I quickly went into sales, and it was to be sales. And so it was like, best education ever, right? Really? What was the product just give a sense of, Gosh, what were you selling?...

Yeah, I mean, now you it'll reveal why I've chosen Square as well. So it was really depository products, investment products, credit and transaction products. The transaction is like wires, credit card processing cards, and so I mean, it's really the same thing that does. Here it's We have a depository product. We have transaction services, which is the core of our business. We have credit for small businesses and So once you start sort of adding those together, you're seeing that it just comes in a different wrapper. And so I went up in the ranks through the S and B side and just loved it. I learned so much, I learned that selling it to S and B s is hard and full of passion. And and really, it's really comforting in that way as well. It's like you matter a lot to the businesses you serve. I went into enterprise sales. Yeah, it was a natural progression. Yeah, it was a natural progression, except that I took a step back from leadership to become an icy, which was which was great for me. Actually. I had my first child by then, and it was nice to have days that were my own and hours that were my own. Like I could set my own schedule as a salesperson, and that was powerful. I want to go for a second because I have so many conversations with revenue collective members and and even, just, you know, friends in the restaurant technology, industry and so forth. And many of them have this fear of going from leadership to I C and look at you know what? That you know, That was obviously a step in the in, perhaps backwards, let's say from a title perspective, but clearly propelled you forward. Oh, no question I would not be. I wouldn't have been a shoo in for the head of sales role here had I not done both SMB and Enterprise, right? Right. And you don't you don't go smb and then to enterprise and then...

...leadership without having carrying a bag in both of those. Yeah, it was definitely I felt safe, though I felt safe doing it because it was a company that I felt like I had built a lot of people equity in, You know, I had a team, a team meeting, like just people in the company that cared for me, and it wouldn't let me fail and, you know, would tolerate me sort of starting over in a different job and and and also be a guide for sort of short cutting. If I needed to, like, you know, they had No. They knew that I could manage a team before and a large team at that. And so I felt safer doing it and now, you know, I hope to build that same type of psychological safety here at Square, like that's That's a real goal of mine. But, um, you know, I say to my team all the time it's not a career ladder, it's a lattice. And so it doesn't it doesn't go up. It goes everywhere and and just be prepared to, like, see those moves as additive. Um, so after a couple of years in enterprise or in Large Corp sales here in Silicon Valley, I had my second kid and I had dinner with a friend of my husband's. Rather that that friend came over for dinner. Yes, and we started talking about square and the rest is history. And so, you know, I feel. But that that friend was at square. Yes, well, I'm assuming at some point yeah, that's right. So we're going to count this conversation as well. Answer a future question of give us an example of luck because having a friend over for dinner doesn't always lead to such an incredible role at a monster company like square. That's so true. That's so true. Nice. Nice. Well, look, that is incredible. And and you've been a square for, what, three years now? Just what's the sense of kind of what you're building there with a 400 plus person team? Um, yeah, it's been almost four years. It will be four years in the summer.

What are we building? We are. We are building a sounds, not super sexy, but it is actually quite exciting and powerful, and that we're building a scalable, un predictable and repeatable machine with a product that's constantly changing and that that that intersection is really exciting because it's like, All right, we're still learning every day. Like if I take every year of sales knowledge and sales leadership knowledge behind me, it still wouldn't be enough for today because it's not those I don't have to moving targets. I don't have the target of scalable, predictable, repeatable Yeah, yada and literally, the product changes every day. An entire new categories are being added on. And so, you know, I'd like to venture to say that we are building really the first ever SMB ecosystem sales team. I have worked on teams that sell something to an SNB. I've worked on team to sell an ecosystem to an enterprise But I haven't quite encountered this real like true intersection of SMB and business ecosystem, and that's what makes it the most exciting. And frankly, you know, Brandon, you know that that's what led me to you. Is this this desire to want to talk to as many people as many different industries as possible and just just hang out with smart people? Because that's how you that's how you grow your knowledge base. Yeah, well, jury's out on the smart part for me, but I think it's incredible to because in this moment where businesses, you know, this will probably air. You know, in March, businesses will probably still be handling the pandemic and so forth. And and frankly, that that is, uh, very hard, right? And and having somebody like square come in and enable you know everything from loans to, you know, just transactions that you do every day really kind of being an...

...advocate for small businesses, mom and pop shops in so many ways. Well, I'm not meaning to gosh, but I do admire the company and and look at what has been built. Their holy cow. Well, give us maybe back. Think back to those icy days Give me Give us a tactic that you think maybe folks in the revenue collective or anyone listening could just use tomorrow sales or marketing. Whatever One tactic tactics give us a trick. How did you get? I don't believe in tricks, but But I will say it served me well from I see all the way today the simple, the simple notion of of structure, the power of structuring your message. So as an i c. And even as a leader, there's this sort of sing song like Say what you're gonna say Say it then say what you said. There is a very powerful connection that you can make with your counter party by just like I'm going to tell you this. This is what I was going to tell you, you know, in review. This is what we talked about today like that, that very clear. It's very comforting for us as humans, right? Similarly, the structuring of creating discomfort and then following buy things that you can agree on or solutions. And that's a really powerful alignment tool as well as like, you know, make people feel the pain of what it is that they're telling you are talking about that their business is going through and then come in with, like, I feel you on that pain like and then walking them through it makes them remember it. And then the solutions that you're providing actually removes that discomfort. And that's very powerful. And I still like today, I like that term, creating discomfort. And it's an interesting thing. Maybe for somebody Day one of sales training. You know, we want you to create discomfort. Clearly, it needs to be in the right hands, but But I love that because it's both creating urgency and demonstrating the...

...problem that you're trying to solve, right? I mean, yeah, I think to what you just said about, like treating with care. It's not like you want to make someone feel bad. It's more like make them remember what they just told you. That sounds That sounds hard. Yeah, when they're like, Yeah, I'm lighting orders across five different ipads in my restaurant. You're like, Oh, like that. That sounds tough, right? Right. I love that. That's a good one. All right. So we'll jump into, you know, kind of wrap up and jump into some of these kind of quicker questions. What's a key position you're hiring for anything in the organization that you know, really looking for somebody to kill a person to join you? Oh, my gosh. So many were. As you know, we're hiring like crazy. Um, but literally hundreds of rolls this year. But one of the more unique roles is open right now. Is the head of sales role for Japan based out of Tokyo So excited about that? Uh, we have a new sales manager role opened in Melbourne and account executive manager roles in all regions in the U. S. So that is super exciting for us. Yeah, I knew once I asked this question. I should just say check out squares website. There is a They're all the roles, but, uh, awesome that you're, you know, obviously hiring in the midst of a time when people don't have jobs. So not everyone has a job. So and then some shout outs. Either folks, that you follow for content or up and comers who you're excited that that they're doing killer things. Maybe in a couple couple rungs, below you or even people you look to his mentors. I mean, I I, uh, believe Mycoskie to shouted out your name as, uh, you know, proud of all the things that you've done. So I'm so grateful for that. The reason why I'm sighing is because I feel like I could be here all day like I really have, like, a very sort of salad approach to to mentorship and keeping an eye on...

...other people. It's like it's someone for something. And, for example, like, I always admire Mike's boldness. Like Mike is, Mike is bold and he like, he gets excited about things that others are like. That's crazy. You call this a salad approach like a little bit of everything. You know, like a salad bar. Like Like I need a little bit of this for the crispy and a little bit. Okay. Exactly. You can't have a salad of just one ingredient. It's boring. Uh, anyway, so I think so. Shout outs of up and comers. Honestly, had I given this deeper thought I would have more for you. But honestly, like I've been so immersed in my world right now, like my my direct leadership team, like Tom Hanrahan ahead of us sales Joey Roll, head of enterprise sales. Julian Alvarez, head of sales Dev Michael Wilson, head of international sales like Those are just but a few, By the way, all of them are RC members. Um, but a few people that are like, really coming into some truly innovative thinking on on how we're going to do business for the next three years. So that's that's That's good. There we go. We didn't I was going to say, You got to text me and we're going to post on LinkedIn for people. But the last one, my favorite question of all, which is give us some place to go eat. Give us a restaurant suggestion that we should go check out. Doesn't need to be near you. Any place you've traveled could be in a hole Hole in the wall could be super fine dining. I love that. Before I answer that one, I'm going to give you the content question that you asked about. Who do you follow for content? Gosh, yeah. Um, I have a friend and a partner at DMG Partners, which is a consumer goods private equity shop for the most mostly consumer goods. But he runs a podcast called Unfinished Biz. Okay, of all the companies that turned his v c r a p e shop down. So all the companies that didn't take funds from...

...his P shab and he basically follows the career. You know, the trajectory of these successful companies and it's the embodiment of, like turning an L into a learning and not a loss and a lot of fun. It's really great to listen to. So if you if you have a walk, go for later. I know you do as I told you to go and walks. You should go on that. Okay, Restaurants. Just what you can do a couple if you want, but what's one? You can't wait and everyone should go to when? When the world reopens. Oh, okay. I love Eldorado. Kitchen up in in the town of cinema right off the square. Alright. That places. So, like, maybe it's just the thing. Like you just had a day in cinema and you're gonna hang out at this like, really fresh and delicious restaurant. But as far as full service restaurants go, I really missed that one. Good. I love it. I've only heard of it and never been there. But now I have a reason to come out to cinema and maybe hang out and go get a coffee with you while they're actually a pleasure, as always, Always love talking with you and certainly learn something each time. Really, Really Looking forward to seeing what 21 brings for you. Thank you, Brandon. Really appreciate it. Thanks for having me on. Absolutely. All right, that's our show. Thank you so much for listening. If you love the show, please rate and review in the Apple podcast or Spotify. Send it to some friends and make sure to subscribe. All those things actually matter. So thank you. A reminder. This episode was brought to you by six cents. Powered by AI and Predictive Analytics. Six cents helps you to unite your entire revenue team with a shared set of data to achieve predictable revenue growth. I had a ton of fun today. I hope you did too. Now get out there and crush your numbers. Say something Mhm.

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