The Pavilion Podcast
The Pavilion Podcast

Episode · 4 months 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 thePavilion podcast. I am your host, Brandon martin you're listening to. Isthis a good time the show where I ask amazing Pavilion members some coolquestions, they have some great answers. We're doing something a littledifferent 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'rerunning some of our most popular episodes of 2021. So I hope you enjoythis episode was brought to you by Inside Square advanced revenueanalytics and forecasting for today's B two B organizations. Your revenue teamwakes up every day with questions inside Square. It gives you the datadriven 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 globalhead of sales of Square and uh somebody who I consider a good friend and I'm soglad to be here with you today and uh, and have you on the revenue collectedpodcasts? Thank you Brandon. I hope you can hear me smiling because I have soI've so enjoyed our friendship this year, especially as the economy is in abit of a spin, it's been it's been great. Thank you awesome, awesome. WellI'm not going to take it easy on my all my hardball questions anyway, Okay. Uhyou know, as everyone who listens knows, you know, we're going to just get toknow 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 gotto be one of the hottest tech companies of the past couple of decades withperhaps one of the best leaders. You know, people put Jack Dorsey up withwith the titans of the startup world, so give us a sense of how you got herelike wow well thank you for that intro... do I even live up to that As yousaid before, I'm the global head of sales at square. I feel immensely luckyevery 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 bemany more countries. Soon to be many more reps. As you know the opportunityis there businesses need better and streamlined more cost effectivetechnology to get them through this time and that which combinestechnologies and so I'm excited to have our team deliver that. How did I gethere? I started my career in traditional financial services and tobe honest I I really appreciated it. I've never in my life was like I'mgonna be a banker. Like nobody says that. I think very few people also grewup in there. Like I'm gonna be in sales. But sure enough I went into I went intobanking because truth be told this because it's an excellent company. Iwent to J. P. Morgan and they were willing to pay for my business schooldegree. So I was like I'm out of there after that and then I stayed for 13years. 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. Andthen after that I quickly went into sales and it was to be sales and so itwas like best education ever right? Really was the product just give asense of gosh what were you selling? Yeah I mean now it'll reveal why I'vechosen square as well. So it was a 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 serviceswhich is the core of our business. We...

...have a credit for small businesses. Andso once 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 S.And 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. Which 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 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'tgo SMB and then to enterprise and then leadership without having carrying abag and 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 alsobe 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 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's a lattice. And so it doesn't, it doesn't go up, it goes everywhere andand just be prepared to like see those moves as additive. Um, so after acouple years in enterprise or in large corp sales here in Silicon Valley, Ihad my second 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 friend was at square,you know, I'm assuming at some point. Yeah, that's right. So we're going tocount this conversation as well answer a future question of, give us anexample of luck because having a friend over for dinner doesn't always lead tosuch 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 beena square for what, three years now? Just what's the sense of kind of whatyou're building there with a 400 plus person team? Um yeah, it's been almost four yearswill 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 and powerfuland that we're building a scalable, un predictable and repeatable machine witha 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... enough for today because it's not, Idon'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 S and B. I'veworked on 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, this, that, that's what led me to you is this, this desireto want to talk to as many people as many different industries as possibleand just just hang out with smart people because that's how you, that'show 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, youknow, this will probably air, you know, in March, businesses will probablystill be, you know, handling the pandemic and so forth. And frankly thatthat is uh, very hard, right? And, and having somebody like square come in andenable, you know, everything from loans to, you know, just transactions thatyou do every day. Really kind of being an advocate for small businesses, momand pop 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 give usmaybe back, think back to those icy days. Give me, give us a tactic thatyou think Maybe folks in the revenue collected or anyone listening couldjust use tomorrow sales or marketing whatever one tactic tactics. Give us atrick. How did you get? I don't believe... drinks. Um, but but I will say itserved 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 aleader there's this sort of sing song like say what you're going to 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 what it isthat they're telling you are talking about that their business is goingthrough 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 sort of removes thatdiscomfort and that's very powerful and I like that term creating discomfortand it's an interesting thing maybe for somebody day one of sales training, youknow we want you to create discomfort clearly it needs to be in the righthands but but I love that because it's both creating urgency and demonstratingthe problem that you're trying to solve right? I mean yeah, I think to what youjust said about like treating with care, it's not like you want to make someonefeel bad, it's more like make them remember what they just told you. Thatsounds, that sounds hard. Yeah they're like, yeah I'm lighting orders acrossfive 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 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 uh but literallyhundreds of rolls this year but one of the more unique roles that's open rightnow is a head of sales role for Japan based out of Tokyo. So excited aboutthat. We have a new sales manager role open in Melbourne and account executivemanager 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 squareswebsite there is a, they're all the roles but uh awesome that you'reobviously hiring in the midst of a time when people don't have jobs so noteveryone has a job. So and then some shout outs either folks that you followfor content or up and comers who you're excited that that they're doing killerthings. Maybe in a couple couple rungs below you or even people you look tohis mentors. I mean I I uh believe Mycoskie to shouted out your name as uhyou know, proud of all the things that you've done. So I'm so grateful forthat. The reason why I'm sighing is because I feel like I could be here allday. Like I really have like a very sort of salad approach to, tomentorship and keeping an eye on other people. It's like, it's someone forsomething 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. Yeah, like a little bitof everything, you know, like a salad bar, like, like I need a little bit ofthis for the crispy and a little bit okay, exactly, you can't have a saladof just one ingredient, It's boring.

Huh? Anyway, so I think so, shout outsof up and comers honestly, had I given this deeper thought I would have morefor you, 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 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 iton linkedin for people. But the last one, my favorite question of all whichis give us some place to go. 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 part mostly consumer goods but he runs a podcast called unfinished bizokay of all the companies that turned his V. C. R. Her Pe shop down so allthe companies that didn't take funds from his pE shop and he basicallyfollows the career. You know the trajectory of these successfulcompanies and it's the embodiment of like turning an L into a learning andnot a loss. It's a lot of fun. It's really great to listen to so if you ifyou have a walk scheduled for later. I know you do as I told you to go andwalks, you should go on that okay restaurants just what you can do acouple if you want but what's one you...

...can't wait and everyone should go towhen, when the world reopens. Oh okay. I love Eldorado kitchen up in in thetown of cinema right off the square. Alright that places so like maybe it'sjust the thing like you just had a day in cinema and you're gonna hang out atthis like really fresh and delicious restaurant but as far as full servicerestaurants go, I really miss that one. Good. I love it. I've only heard of itand never been there but now I have a reason to come out to cinema and maybehang out and go get a coffee with you while they're actually A pleasure asalways, always love talking with you and certainly learn something each time.Really really looking forward to seeing what 21 brings for you. Thank youBrandon, really appreciate it. Thanks for having me on. Absolutely that isour show. Thank you so much for listening. If you love the show, pleasewrite a review in the apple podcast or Spotify have sent it to some friendsand make sure you smash that subscribe button a reminder. This episode wasbrought to you by drift the new way businesses buy from business is areminder. This episode was brought to you by insight Square. Say goodbye tospreadsheet, forecasting and hello to serum data. You can trust inside Squaredelivers predictive deal scoring, unmatched visibility and inspection andadvanced goal management for your entire team. Everything you need totake back control of the revenue process. Say something. Mhm.

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