The Pavilion Podcast
The Pavilion Podcast

Episode · 1 year ago

Ep 129: Creating Discomfort w/ Ashley Grech


Ep 129: is a throwback to Ep 49. Creating Discomfort w/ Ashley Grech

Part of the "Is This A Good Time?" series hosted by Brandon Barton. 

Hello everyone and welcome back to the Pavilion podcast. I am your host, Brandon martin you're listening to. Is this a good time the show where I ask amazing Pavilion members some cool questions, they have some great answers. We're doing something a little different today and for the next two weeks, just like everyone, you know, your favorite podcast takes a little holiday at the end of august. We're running some of our most popular episodes of 2021. So I hope you enjoy this episode was brought to you by Inside Square advanced revenue analytics and forecasting for today's B two B organizations. Your revenue team wakes up every day with questions inside Square. It gives you the data driven answers in real time. Get 350 out of the box reports and dashboards. Self service. No co all right, we are here with Ashley Greg. 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 Brandon. 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, 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. Uh you know, as everyone who listens knows, you know, we're going to 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 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... do I even live up to that As you said before, I'm the global head of sales at square. 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've 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 this because it's an excellent company. I 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 was the product just give a sense of gosh what were you selling? Yeah I mean now it'll reveal why I've chosen square as well. So it was a 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 a 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. Which 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 and 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 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 friend was at square, you know, 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. It's not 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 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... enough for today because it's not, 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 S and B. 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, this, 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, 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, you know, handling the pandemic and so forth. 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 collected 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... drinks. Um, 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 I see and even as a leader there's this sort of sing song like say what you're going to 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 sort of removes that discomfort and that's very powerful and 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 they're like, yeah I'm lighting orders across five different ipads in my restaurant. You're 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 uh but literally hundreds of rolls this year but one of the more unique roles that's open right now is a head of sales role for Japan based out of Tokyo. So excited about that. We have a new sales manager role open 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 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. Yeah, 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.

Huh? 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 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 it on linkedin for people. But the last one, my favorite question of all which is give us some place to go. 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 part mostly consumer goods but he runs a podcast called unfinished biz okay of all the companies that turned his V. C. R. Her Pe shop down so all the companies that didn't take funds from his pE shop 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. It's a lot of fun. It's really great to listen to so if you if you have a walk scheduled 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 miss 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 that is our show. Thank you so much for listening. If you love the show, please write a review in the apple podcast or Spotify have sent it to some friends and make sure you smash that subscribe button a reminder. This episode was brought to you by drift the new way businesses buy from business is a reminder. This episode was brought to you by insight Square. Say goodbye to spreadsheet, forecasting and hello to serum data. You can trust inside Square delivers predictive deal scoring, unmatched visibility and inspection and advanced goal management for your entire team. Everything you need to take back control of the revenue process. Say something. Mhm.

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