The Pavilion Podcast
The Pavilion Podcast

Episode · 7 months ago

Ep 49: Creating Discomfort w/ Ashley Grech

ABOUT THIS EPISODE

Ep 49: Creating Discomfort w/ Ashley Grech

Hello, everyone. And welcome back tothe revenue collected podcast. I am your host, Brandon Martin, and you'relistening to Is this a good time? The show where I asked revenue collectedmembers some really basic questions, and they have incredible answers in ashort, 15 minute conversation will be coming to you live Tuesdays andThursdays each week. So smash that subscribe button so you don't miss anopportunity to learn from members of the RC community, any of which,especially this one today. Who could be your future boss? Our guest todaymanages 400 people. So maybe she is your boss, Ashley Greg, the global headof sales at square. And we talk about why you might want to start makingprospects have been uncomfortable before we get going with the questionsI want to tell you a little bit about this month Sponsor. It's six cents sixcents. The number one account engagement platform helps you toidentify accounts that are in market for your solution. Prioritize yourefforts, engage buyers the right way with highly relevant messaging andmeasure what actually matters with the six cents platform, you're able to getinto more deals, improve win rates increase overall pipeline and optimizedbudget 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, weare 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 youtoday. 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 ourfriendship this year, especially as the economy is in a bit of a spin. Um, it'sbeen It's been great. Thank you. Awesome. Awesome. Well, I'm not goingto 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 getto know Ashley and learn about her and her career. So bring us through that Imean this, you know, it's not...

...overstating it to say that you are in atremendously large position in a publicly traded company that has got tobe one of the hottest tech companies of the past, you know, a couple of decadeswith perhaps one of the best leaders, you know, people put Jack Dorsey upwith with the titans of the startup world. So give us a sense of how yougot here. Like, Wow, Well, thank you for that intro. How do I even live upto that? As you said before And the global head of sales, That's where Ifeel 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 whichcombines 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, andto be honest, I I really appreciated it. I never in my life was like I'm gonnabe a banker like nobody says that I think very few people also grew up inthere like I'm gonna be in sales. But sure enough, I went into I went intobanking because truth be told us, because it's an excellent company. Wentto 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 helda number of roles there, though one was like a strategy based role. And thenafter that, I quickly went into sales, and it was to be sales. And so it waslike, best education ever, right? Really? What was the product just givea sense of, Gosh, what were you selling?...

Yeah, I mean, now you it'll reveal whyI've chosen Square as well. So it was really depository products, investmentproducts, credit and transaction products. The transaction is like wires,credit card processing cards, and so I mean, it's really the same thing thatdoes. 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 Soonce you start sort of adding those together, you're seeing that it justcomes in a different wrapper. And so I went up in the ranks through the S andB side and just loved it. I learned so much, I learned that selling it to Sand B s is hard and full of passion. And and really, it's really comfortingin that way as well. It's like you matter a lot to the businesses youserve. I went into enterprise sales. Yeah, it was a natural progression.Yeah, it was a natural progression, except that I took a step back fromleadership to become an icy, which was which was great for me. Actually. I hadmy first child by then, and it was nice to have days that were my own and hoursthat were my own. Like I could set my own schedule as a salesperson, and thatwas powerful. I want to go for a second because I have so many conversationswith revenue collective members and and even, just, you know, friends in therestaurant technology, industry and so forth. And many of them have this fearof 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 atitle perspective, but clearly propelled you forward. Oh, no questionI would not be. I wouldn't have been a shoo in for the head of sales role herehad I not done both SMB and Enterprise, right? Right. And you don't you don'tgo smb and then to enterprise and then...

...leadership without having carrying abag in both of those. Yeah, it was definitely I felt safe, though I feltsafe doing it because it was a company that I felt like I had built a lot ofpeople equity in, You know, I had a team, a team meeting, like just peoplein 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 bea 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 soI felt safer doing it and now, you know, I hope to build that same type ofpsychological 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'sa lattice. And so it doesn't it doesn't go up. It goes everywhere and and justbe prepared to, like, see those moves as additive. Um, so after a couple ofyears in enterprise or in Large Corp sales here in Silicon Valley, I had mysecond kid and I had dinner with a friend of my husband's. Rather thatthat friend came over for dinner. Yes, and we started talking about square andthe rest is history. And so, you know, I feel. But that that friend was atsquare. Yes, well, I'm assuming at some point yeah, that's right. So we'regoing to count this conversation as well. Answer a future question of giveus an example of luck because having a friend over for dinner doesn't alwayslead to such an incredible role at a monster company like square. That's sotrue. That's so true. Nice. Nice. Well, look, that is incredible. And andyou've been a square for, what, three years now? Just what's the sense ofkind 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 arebuilding a sounds, not super sexy, but it is actually quite exciting andpowerful, and that we're building a scalable, un predictable and repeatablemachine with a product that's constantly changing and that that that intersection isreally exciting because it's like, All right, we're still learning every day.Like if I take every year of sales knowledge and sales leadershipknowledge behind me, it still wouldn't be enough for today because it's notthose I don't have to moving targets. I don't have the target of scalable,predictable, repeatable Yeah, yada and literally, the product changes everyday. An entire new categories are being added on. And so, you know, I'd like toventure to say that we are building really the first ever SMB ecosystemsales team. I have worked on teams that sell something to an SNB. I've workedon team to sell an ecosystem to an enterprise But I haven't quiteencountered this real like true intersection of SMB and businessecosystem, 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 wantto talk to as many people as many different industries as possible andjust just hang out with smart people? Because that's how you that's how yougrow 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, youknow, this will probably air. You know, in March, businesses will probablystill 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 enableyou know everything from loans to, you know, just transactions that you doevery day really kind of being an...

...advocate for small businesses, mom andpop shops in so many ways. Well, I'm not meaning to gosh, but I do admirethe company and and look at what has been built. Their holy cow. Well, giveus maybe back. Think back to those icy days Give me Give us a tactic that youthink maybe folks in the revenue collective or anyone listening couldjust use tomorrow sales or marketing. Whatever One tactic tactics give us atrick. How did you get? I don't believe in tricks, but But I will say it servedme well from I see all the way today the simple, the simple notion of ofstructure, the power of structuring your message. So as an i c. And even asa leader, there's this sort of sing song like Say what you're gonna say Sayit then say what you said. There is a very powerful connection that you canmake with your counter party by just like I'm going to tell you this. Thisis what I was going to tell you, you know, in review. This is what we talkedabout today like that, that very clear. It's very comforting for us as humans,right? Similarly, the structuring of creating discomfort and then followingbuy things that you can agree on or solutions. And that's a really powerfulalignment tool as well as like, you know, make people feel the pain of whatit is that they're telling you are talking about that their business isgoing through and then come in with, like, I feel youon that pain like and then walking them through it makes them remember it. Andthen the solutions that you're providing actually removes thatdiscomfort. And that's very powerful. And I still like today, I like thatterm, creating discomfort. And it's an interesting thing. Maybe for somebodyDay 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 bothcreating 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 withcare. It's not like you want to make someone feel bad. It's more like makethem 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 inmy 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'sa key position you're hiring for anything in the organization that youknow, 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 hundredsof rolls this year. But one of the more unique roles is open right now. Is thehead of sales role for Japan based out of Tokyo So excited about that? Uh, wehave a new sales manager role opened in Melbourne and account executive managerroles in all regions in the U. S. So that is super exciting for us. Yeah, Iknew once I asked this question. I should just say check out squareswebsite. 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 youfollow for content or up and comers who you're excited that that they're doingkiller things. Maybe in a couple couple rungs, below you or even people youlook to his mentors. I mean, I I, uh, believe Mycoskie to shouted out yourname as, uh, you know, proud of all the things that you've done. So I'm sograteful for that. The reason why I'm sighing is because I feel like I couldbe here all day like I really have, like, a very sort of salad approach toto mentorship and keeping an eye on...

...other people. It's like it's someonefor something. And, for example, like, I always admire Mike's boldness. LikeMike is, Mike is bold and he like, he gets excited about things that othersare like. That's crazy. You call this a salad approach like a little bit ofeverything. You know, like a salad bar. Like Like I need a little bit of thisfor the crispy and a little bit. Okay. Exactly. You can't have a salad of justone ingredient. It's boring. Uh, anyway, so I think so. Shout outs of up andcomers. Honestly, had I given this deeper thought I would have more foryou. But honestly, like I've been so immersed in my world right now, like mymy direct leadership team, like Tom Hanrahan ahead of us sales Joey Roll,head of enterprise sales. Julian Alvarez, head of sales Dev MichaelWilson, head of international sales like Those are just but a few, By theway, all of them are RC members. Um, but a few people that are like, reallycoming into some truly innovative thinking on on how we're going to dobusiness 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 onLinkedIn for people. But the last one, my favorite question of all, which isgive us some place to go eat. Give us a restaurant suggestion that we should gocheck out. Doesn't need to be near you. Any place you've traveled could be in ahole Hole in the wall could be super fine dining. I love that. Before Ianswer that one, I'm going to give you the content question that you askedabout. Who do you follow for content? Gosh, yeah. Um, I have a friend and apartner at DMG Partners, which is a consumer goods private equity shop forthe 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 thecompanies that didn't take funds from...

...his P shab and he basically follows thecareer. You know, the trajectory of these successful companies and it's theembodiment of, like turning an L into a learning and not a loss and a lot offun. 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? Youcan'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 hada day in cinema and you're gonna hang out at this like, really fresh anddelicious restaurant. But as far as full service restaurants go, I reallymissed 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 acoffee with you while they're actually a pleasure, as always, Always lovetalking with you and certainly learn something each time. Really, ReallyLooking forward to seeing what 21 brings for you. Thank you, Brandon.Really appreciate it. Thanks for having me on. Absolutely. All right, that'sour show. Thank you so much for listening. If you love the show, pleaserate and review in the Apple podcast or Spotify. Send it to some friends andmake sure to subscribe. All those things actually matter. So thank you. Areminder. This episode was brought to you by six cents. Powered by AI andPredictive Analytics. Six cents helps you to unite your entire revenue teamwith a shared set of data to achieve predictable revenue growth. I had a tonof fun today. I hope you did too. Now get out there and crush your numbers. Say something Mhm.

In-Stream Audio Search

NEW

Search across all episodes within this podcast

Episodes (155)