The Sales Hacker Podcast
The Sales Hacker Podcast

Episode · 3 years ago

57. How to Build Yourself Into a Great Manager w/ Ashley Grech, Global Head of Sales, Square

ABOUT THIS EPISODE

This week on the Sales Hacker podcast, we speak with Ashley Grech, Head of Sales at Square. She discusses how she transitioned into her role at Square by first being the best person you can be in your role. Join us as we discuss how to invest your time into a company before taking the next step in your sales career.

One, two, one, three, three, hey everybody, it's Sam Jacobs. Welcome to the salesacker podcast. We're so excited this week we've got Ashley Grek, the Global Head of sales for square. Square is a thirty billion dollar market CAP company that is an all encompassing payments and commerce business that serves the small medium sized businesses of the world. It's incredible company and Ashley talks to us about how she spent a long time in the banking world before making the jump into sales leadership at square and how she thinks about team building, what her core principles are around team building and how she develops and helps people develop their own personal careers and career progression through some of the principles that she outlines in the interview. So it's a great interview. Ashley's incredibly impressive executive and leader and we're so excited to have her on the show. Now, before we jump into the show, as always, of course, we have to thank our sponsors. So our first sponsor is show pad. Show pad is the leading sales enablement platform for the modern cellar. It's the industry's only unified sales enablement platform combining sales content, training, coaching and conversations. It's a one stop shop for your sales team to prep and deliver the best buying experiences for your clients, and it integrates with your core sales and marketing system such as sales force, Microsoft Dynamics, outreach, Marquetto g suite, outlook, etc. So learn more at showpadcom forwards. SALESAC heard and our second sponsor is the leading sales engagement platform outreach. Outreach support sales reps by enabling them to humanize communications at scale, from automating the soul sucking manual work that eats up selling time to providing action oriented tips on what communications are working best. Outreach as your back. Now, without further ado, let us listen to today's interview with Ashley Grek. Everybody, it's Sam Jacobs. Welcome back to the salesacker podcast. We are fortunate and delighted to have this week's guest on our show, Ashley Grek. Ashley is the current head of sales at square. If you haven't heard of square, then you're probably one of the few people in the universe, and she's leading a global team and she's going to talk to us about what she's doing at square and how she's building that team and how important process is to the development of that team. But you should also know that Ashley is a leading both commercial and just overall executive in Silicon Valley. She spent a long time in investment banking, understanding the skills, the qualities, the drivers of enterprise value within the technology industry before moving into formally operating roles, currently at square, and she's going to talk to us work. So excited to have her. Ashley, welcome to the show. Thank you so much for having me. Sam. We are excited to have you here. So we have this little thing that we call your baseball card, which is where we we can textualize your expertise. We learn a little bit about your background. So it's Ashley Greck. You're the current head of sales at square. We give you an opportunity to tell us what, in your words, to square do. What is square? Square is so many things. I think we're best known for being a point of sale company. You know, once upon a time we were the little white reader that came in and sort of changed a payments market, one where you had to walk into a bank apply to get a point of sale or a merchant services account. After A to week application and, you know, request for your firstborn child's blood, you may or may not be approved. So Square has really evolved, though, from being this little white reader to a full scale commerce platform. It's currently around two billion dollars in revenue, thirty billion a market cap and recently named Yahoo Finance Company of the year for two thousand and eighteen gratulations. Were so excited. The companies about ten years old, but this is the fifth year first square sales team to be around. Wow, one of the things I want to thank you for. I want to thank you for making moving from the Brooklyn artismal shops saying they only accept cash to saying they don't accept cash at all, they only accept credit cards, and I think square has a big has a big influence on that decision. So thank you for removing cash from our economy and driving towards easier transactions. That is so nice to hear. I don't carry catch now and I'm like that that person that never has cash with them. So I am absolutely a product of the company I work for, for sure. Yeah, it's it was. It's been a revolutionary company for the small businesses so because it's just transformed a single merchant's ability to build a business and accept all of the different forms of payment through out there. So I think it's just an incredible company. Tell us about your sales organization. It's such a great and unusual org I know everyone says that, but I just I couldn't mean it more so. Our sales organization at square is just under two hundred people in a number of different functions, over half our a's, and then it includes sales dev and lead call sales, strategy and operations, enablement and productivity solutions, engineering, professional services and implementation support. We have reps. they're mostly in the US, around two hundred or in the US, but we have reps in...

Tokyo, Melbourne, London and Toronto and growing quickly, which is a real testament to how quickly the product is evolving. But we just you know, square sales team is here to show value to a product company and it's been quite a red tell me what you're selling. Are you selling sort of a suite of kind of backoffice solutions or payment processing solutions to small medium sized businesses, or is it something else? That's a good question. We have a little something for everyone. We call ourselves a commerce platform because I don't think we're just a payments company. It's not just about the payment itself, although if you think about like your interaction at a starbucks, like the payment, the commerce interaction is why you came there. You didn't go there to say hello, you went there to buy caffeine, and so the the monetary exchange is is the crux of the relationship. But we sell the ability to take payment, the hardware on which to take payment, the background, like analytics on how to run the business and view sales throughout the day and across locations. We sell payroll for employees and benefits. We sell I didn't know that. Yeah, we sell small business capital, which is pretty incredible to see a multilocation business sort of be able to like fund inventory or fund the expansion of their business through square. We Sell Appointments, Marketing Services, loyalty tracking and for much larger corporations, we have our API and SK sweet too, for them to be able to build the experience as they want with. So this is really like a global financial conglomerate. I mean you're doing a lot of different things. We are. We're doing a lot of different things, and really it's about we talk a lot about how it's that the experience that a business owner wants to have. You know, how it's not just about how quickly someone can get through a line. Right, we have, I'm selling square now, but like we have the fastest line speed around. We have to second transaction. So if anyone's ever stood in a line at a stadium before waiting for a hot dog, you're like all the one is a hot dog, like just get me through your faster. But it's not just about that. It's about like interacting with your customer, using marketing and loyalty to bring them back and then also tracking that type of behavior. So, yeah, well, and it is one of the two companies that the estimable Jack Dorc is CEO of, if I'm not mistaken. Yes, that's right. Right, so let's figure out how you got here, because I think, is it true that you've been at square for just under two years and then before that you were bigger companies. So talk to us a little bit about you know, we like to know. We do like to know about your personal background, where you're from, and you know where you grew up, and then how how you found your way to the bay area and also, of course, as I mentioned in the Intro, would love to know a little bit about your banking experience and how that led you to square. Sounds good. So I've not been square along. You're right on that. I've been here for just under two years, which I like to joke is just enough time to break old habits and learned to bring out the best in both sort of old world and new world. Now, the old world is that I spent the last almost thirteen years in banking. I started in like a finance and strategy role and also I did a short stint in marketing, but I joined sales in two thousand and seven during the financial crisis. I just at that time it was like I wanted to have a number that showed that showed my value every day as a young professional. That just seemed right to me, particularly at a time where I think banks were looking for ways to cut people, to be perfectly honest. And where you were you doing sales at? We you in institutional equity sales or what kind of sales are you doing? No, I was in small business sales at that time. So it was like wow, it was the toughest education. It was my first sales job. First of all, I'm selling two small and medium sized businesses in what what was a a brutal economic downcurn from the position of a bank. So I just felt like it was one of the most hated and contested industries one of the toughest times to be selling. It taught me so much about understanding the perspective of the customer and then understanding the product, because for me, like for any smart professional, I think it's like I'm just going to read this book and I'm going to regurgitate it to you right, but that that just didn't work at that time. It was such an emotionally charged time for small businesses. So I really learned and I was I learned from the best. I had some fantastic colleagues about learning how to connect with a customer and maybe that's the reason why I love sale so much. It's just it never really felt like a sale. I got to be a partner in a business early on and I an advisor or consultant at a young age and that was really empowering to me. I feel that that way it's square as well. It's never it's never a hard cell, but it is an education and it's Square. We're selling something that doesn't have a real partner in the market. There are competitors in every segment, in hardware, in payments, in, you know, payroll and capital, but nobody does all of...

...these things and so having to educate customers like that feels very true to my sort of original sales roots. But my overall story at JP Morgan was that I serve small to medium sized businesses to start and I managed to team and was brought out to California to sort of expand the footprint here. Once a chase brought bought Washington mutual and really expanding the territory. When I arrived that were there were eight or nine's and when I left that group there were a hundred and fifty in the same territory. It well and you they all work for you in different formats, but there were a number of so we had divided, we had rapidly divided that territory. So becoming a manager of managers early on was an interesting time. And then I went on to enterprise because that was, I felt like the next frontier of a skill that I wanted to learn, and so learning to serve large corps in the bay area and that was exciting because just this is silicon valley. There are a ton of fast growing companies with needs that evolved every month, and so that was a fantastic education for me prior to coming to square and sort of building out, coming here to build and we're sustainable sales team here. When you you mentioned just now moving from, I think, being a manager to being a manager of managers. What do you think? What was that journey like and what do you think, in your opinion, are the key skills that are different between being a single, you know, frontline manager, where you have, you know, seven to eight direct reports, and a manager of other managers? One of the toughest transitions. I can't speak to like teaching it, but I think I'll speak to about my own personal journey. They're one of the toughest movements, first from becoming it, from going from I see to a manager, and then and going from a manager to a manager of managers. Is the strength of your communication skills, and I say that I know it sounds traite, but you really you find that you have to work through people and so giving them the type of instruction that's not a direct like follow the Rule Book Instruction, but rather coaching them to sort of see something on their own and how to find their own words that feel true to them. It's helped me be a much better communicator and rather force me to be that just to be able to work through someone is so much more challenging and rewarding because your impact is sort of spread out and more disparate, but that sort of organization of thought and and of communication has been a real difference maker for me. Are there cadences, rituals, tactics? Are there things that you've developed over time to do that, to communicate through other people? Because I think that's a very it's an important point. I wish it were more scientific, but the truth is I spend the at least the first half of any one on one with my regional managers or regional leads talking about people, because I believe that through that and through sort of situational coaching, I can help them brainstorm, help them think think through problems and how to address it. Together we see the bigger picture, and I mean most of the challenges of management or leadership is people, and I say challenge just be not because it's tedious, but only because it takes a hundred different forms every day and you rarely see the same thing twice. So it's just been like walking through it together. It builds trussed between me and my managers and also then builds trust between them and they're directs and allows them to sort of speak with their own voice, handle it their own way and without me. Do you have a set of maybe I don't know if they would be ethics or maybe principles, principles that guide you because, to your point, all of these situations, all of these interactions are different, but are you working from sort of a core, foundational set of principles that that guide you're at the advice that you give or the coaching that you give? Wow, that's deep, Sam. Sorry, it's okay. You know. It's funny you ask because I talk a lot with my leads about I believe in like an a creative mindset, not a deficit mindset. So that's also like a an evolving feeling for me. Like I think as a fixer, as someone who's like a recovering I call myself a recovering perfectionist, but as someone who loves to fix things like in my personal life and and and professionally. That is a deficit mindset, that that implies that like something is below zero, it's negative and you need to sort of get back to zero. But if you're always getting to zero, you're not really getting ahead right. So I try to set our sights as a leadership team really far in the future and and everything sort of flows right. If you can set your eyes on on the prize, then the...

...steps in that are intermediate. If you can all agree that you want you want something together as a team for the future, then you're sort of haggling on how to get there. So that first is to set the vision for the organization, and we do have like a a square sales vision and what we want to be as an org and as our contribution to the company. Then the second thing to think about is, like who are we as leaders to get us to that place? So if you were to say, you know, we're currently a thirty billion dollar company. Today, if we were to say we are the sales leadership team for a hundred billion dollar company, what would that mean on the street? Like if you were to meet someone that said I'm the regional you know, I'm the western region sales leader for a thirty billion of six, sorry, a hundred billion dollar company. What does that mean to you? What would you expect from them? And we work backwards from there and and talk about the type of person or like Credo we want to bring to each and everyone of our reps. and so we do have a couple of themes that we rest on and that we really that we really try to bring to every interaction with our reps. one is a positive energy, bringing that positivity every day and and showing people that sales is hard, but we're a happy bunch. Like we're grateful, which leads me to my second point. The second is that we are appreciative of what we have. I often say that I would not choose any other problems. These are mine and I choose them. And because I choose them, I am accountable, which is the third one. I'm accountable to my team, I'm accountable to our executive team. I think that sort of personal and disparate accountability. If you take ownership of what you do every day, then your team trusts you to make the best decisions for them and that trust that you have their best outcomes in mind. And the fourth is trust. We want to be trusted, we want to trust each other, because that sort of trust and transparency is is incredibly important in the grander scheme of change management and being in an organization that evolves daily. And then, finally, our team trusts us to be visionaries, to see around corners that they don't see. I think what's tough about being a salesperson is, like you have a goal, it's monthly or quarterly or whatever cadence that looks like, and it's easy to sort of to fixate on that and then often times, a year or so into it, you look up and you're like where am I like, where am I going? Where is this organization going? Why am I doing this? And trusting your leaders to have that vision to see around corners for you, I mean your best interest, is key. So those elements of our personalities and traits that we bring to the table as a leadership team, I think are absolutely critical to building the right culture here. But that sounds sounds like you've got you got the foundation in the tenets of something really special. You know, one of the things that we were chatting about before is sort of this concept of a false divide between startups and established companies and you spend a long time at JP Morgan and now you're at square and squares. In a sense it's to start up. In the other sense it's a thirty billion dollar public company. But walk us through this concept of this false divide and maybe some of the things that you can get from a highly structured environment and the things that you can get from an unstructured environment. I think the false divide is is a narrative that people like to say here. They like to talk about in silicon value in particular. It's like, Oh, I'm a I'm a startup guy, I could never go I could never work in a larger corporation or or people see themselves as sort of more organized and structured and wanting to be at a more established company. And there's nothing wrong with sort of wanting to feel like you belong somewhere, but I do think that there is a bit of a false division between the two. Some people think they belong in one of the other. But I feel really lucky to have worked in a very structured environment. I think it was the best sort of sales education and business education I got early on. As well as currently working in an environment that's less structured, with fewer boarders and is is incredibly fast growing. I think there's huge lifetime benefit it to learning a disciplined approach. What I mean by that is having called requirements and having Kpis that are known by all and followed by all in a sales team. I think that's really super important to any to any sort of organized cadence based business, and then on learning the rules just enough so that you kind of fill the space. I say fill the space a lot with my with my team here. That means if you see a gap, if you see something that's not working or that you'd like to change, guess who's the Diri? That's you, like you're the new you're the Dow. You're in charge of that. Fill it. Don't ask for permission if things aren't happening. Actually, I think we trust each other here to know that it's probably a bandwidth thing, so you should just go for it and there's there's no sense of sort of staying in your...

...lane. So I think that combination of having very clear Kpis so that we as an organization agree that that's how we achieve our goals, and then going beyond our goals and filling lanes that we didn't think we as individual reps could occupy. That's a huge career accelerant at square. I like to joke that when I interview people when they come into square, I ask them like where do you see yourself in, you know, three to five years, and I think about fifty percent of the time I hear like I'm going to be head of sale somewhere. You like, that's awesome. I'm proud that they that they see themselves that way. But we have a lot of people from our sales team going into the product teams, into marketing, and it's it's really neat to see that. Like Square is a type of place that we have a close connectivity with, with the product teams, and enough so that this like fill the space culture allows them to grow into a space that they didn't know they can take up. Yeah, one of the concepts you that you've sort of talked about in the past is this concept of career progression as a series of concentric circles. Are Correct me if I'm a misstating that, but talk to us about what that means and you know what the background in the context is for it. I get a lot of questions from reps, managers, managers of managers on my team like how can I how can I grow? What can I do next? How can I continue to push myself? And I draw a series of concentric circles, and I talked about that as their sort of career progression plan and it's also a way of creating like explosive change at square. The first circle is your job, right, that is that is your job description. That's the one that we posted online, and if you're not doing that well, you really don't have time to do the other stuff. So that's that's sort of a nonnegotiable, like hey, your targets, right. But the second concentric circle is is how you do it, how you serve your team, your peers. So if you think of the first circle as you and the second circle is like the people that are immediately around you, how do you make their lives better? Your partners? How does your team feel about you as a manager, for example, to have high morale on your team, do you sort of create culture with them? Like that's the extra credit and that's the second concentric circle and that gives you a lot of leeway to influence the organization. The third concentric circle is like what are you doing for the company, right above and beyond our team, and you earn the ability to sort of stretch into the next concentric circle. And where the magic happens is in that third concentric circle, when you're serving square and when you're serving the company, you get other people in which you get this cool then diagram effect of them overlapping with that outside circle, like they are also doing cool things for the company. And that has been that's just the ability to to do you meet other people in that circle across the company and you can do really cool shit together. That's exciting. I yeah, I mean it's exciting, it's it's a really good frame and night and as you talked about, you said, is it filled the space? Is that what you that's your phrase and it's clear. It can be an empowering concept when you're in a culture where you're saying hey, there's there's open opportunity for you, as opposed to to your point, you know, viewing everything is sort of like a deficit mindset where everything is broken and you need to get it back to zero. I think that's open in sales because we have a very you know sales. You ever very clear mindset of what you need to do every day and knowing that doing that also unlocks the door to something bigger and different for you is can be very empowering. Yeah, yeah, definitely. We've talked about diversity a little bit on this on this podcast and I'm sure you have opinions on it. I think it means a lot of different things. When you think about building diversity into square, how do you approach it? What are your key tenants, principles again, and how do you build it and indoctrinated into the core, you know, DNA of an organization and your opinion. It's funny. I think people recognize it's hard to explain or identify when you don't feel something until it becomes more extreme, and so I've had both spectrums where people have really identify. Like, I appreciate that squares sales team is an incredibly diverse it's over fifty percent women. We hire a ton of diverse thought and Industry and ethnicity, but in our minds I don't really want to focus just on gender ethnicity. I think that's kind of I think that's weak. It's not it's not complete. We serve. Let me take a step back. The reason why diversity is so important to me and to square is truly a business reason. Yes, I want to create a really inclusive environment for my team and one in which will never be in a room and yes each other to death because we're all the same. That is super important to me from a business standpoint. But the truth is we hire because we serve small business sell mostly small business sellers in...

...the US that are incredibly diverse from each other. A small business owner in California or on the coasts will behave very differently than our small business owners in Kentucky or Arkansas or even Missouri. Like we have a sales team in St Louis and their approach is a little bit different and it just works right. There is the element of having diversity of thought and diversity of industry. So what does that mean for hiring? Today? We don't. We actually try not to hire aggressively from tech companies. There's a couple reasons for that. One is that squares really unusual from a technology platform standpoint in that we have a lot of products. So we want to make sure that people can come in and sell an entire ecosystem and not just one thing and get a contract. And I'm not I'm not knocking that type of sale. I just know that that's not all we are and we just haven't. It's really hit or miss on whether or not that successful for us when we hire in a certain profile. So we've started hiring out of like food and beverage or medical device sales or pharmaceutical sales and just having that diversity of knowledge around how to talk to doctors and how to talk to restaurant owners like contractors. It's just been really interesting to see the accelerative effect on how quickly those as can ramp when they speak to something they know about. That is not what we do at square every day, right, like talking to highly tech savvy companies. That it's just not us. We don't. We talk to small business owners and they don't have time for us and they just want someone who understands your business. And so we've really done we feel it's really important as a company to serve every demographic. Similarly, I think having a really diverse team here means that we push each other from a career, growth and mentorship standpoint, but everyone brings something different to the table and it's been really neat to see that sort of come to life over the past couple of years. I know that you focus a lot on process have you what are the processes that you've put into place to source candidates from a bunch of different places, and then what are the processes you put in place, because they are coming from different industries, to get them up to speed? Talk to us about, you know, the training and the investments you make in essentially enablement to help people from all these diverse backgrounds become successful at square? That's a good question. First, on the hiring side, we work very closely with our people team to sort of adjust the profile core recorder and you're a rear and we sort of pay close attention to ramp cohorts and how each ramport cohort has performed. Over the past year and a half, I would say we've really made a shift to try to bring in people from what we know to be very tough and discipline sales industries and the content we can teach them. It's a tough product to learn because there's so much of it and it's highly technical, but if they sort of brick come in with the right attitude and perhaps if they've come in from a really tough sales environment. Some some examples are like ATP. I mean that is, people that have sold an ATP. Like those guys are so well trained, very well trained, the hard, very extremely well trained, work their asses off and and frankly, they know what sort of sales discipline feels like. So that's just one example. But really diversifying the types of organizations resource from. So that's a that's like a monthly sync with our recruiting team to make sure that we are recruiting on on the right types of not the right a diverse enough group of companies. And then on the enablement side, I have a firm belief that first and foremost we need to get the ball. You can't shoot the ball if you don't get the ball, and so our sales training is broken up into sort of three three pieces. One is sales skills and I'm dedicated to building a best in class organization. I was lucky enough to work at JP Morgan for so long and there was a very strong feeling on the street that if you were credit trained at Morgan, that was it, like people knew what that meant. That was that has signal value on the street. It was best in class credit training and I want square sales to be that way for sales training. So we focus a lot on sales skills. Then our secondary focus is on process, like how do you create and convert leads? How do you manage your pipeline? What does a one on one look like? What does your calling process look like? How do you let a discovery call unfold and how do you sort of keep track of the information afterwards? And then finally, we teach product and that all of those are ongoing processes for sure. But, like I said, if you can't get the ball, we're not going to shoot the ball, we're not going to talk about product. We don't even have an opportunity to. So really thinking about how to develop comfort in the sales process and we want this place to be a place where you can sort of grow up in sales, like you can start with your it being your first or second job out of college, and really continue here for a long time.

Is there anything so am I correct? You know, if you if you're a JP Morgan for so long, I would hesitate to call that sort of being INTAC would you agree, Jamie diamond likes to say that there are technology they're trying to agree with that. Well, my I guess where I'm going with this is, I mean you're in the bay area but but you know, at a bank and now you are squarely in the world. Squarely, Pun not intended, but presented itself squarely in the world of Tech. Is there anything that's surprised you about the quote unquote, you know tech industry, Silicon Valley, to the extent that you weren't as aware of it from, you know, from a slightly outsider perspective. You know, what are the things that have sort of surprised you about square that that you hadn't anticipated? A few things, but they're really about square. I can't speak to other organizations with the Silicon Valley because I know that they're not the same everywhere. But two things that really surprising about square is one is this like true dedication across the company to bring and really excellent people in every category and just everyone I interact with here is great. And the second thing, actually there are three. The second thing was about squares viewpoint on performance, not performance on a development and here performance reviews are about what makes you good at your current role and what can you do that will make you better at it? And that coming from coming from banking, is different in that banking is a fixed set of information. You either really know it or you don't. Write. You know how to underwrite a syndicated loan or you don't, and you you know how to underwrite a small business loaner you don't. But here it's like how can you what can make you better your job? And so it took me a little while to be like, is that real? Like that can't be real, but it is, and that is the mindset that people have here. They're like this is what it's going to make you better and they're completely transparent about it and it's really refreshing actually. So I went through a solid like six months of like not believing that that was a real thing and then realizing that that is exactly, is exactly they mean it here. And the third thing is the idea of the comfort around filling the space. So career progression here is often about how well you're able to solve problems, which is really empowering in many ways in finance and, I assume, in accounting and another sort of related industries. Career Russian is, of course how you do the job, but a lot of it is knowledge based. So I'm grossly over simplifying here, but in order to become you know, from a level one to a level three, I see it's like you basically have to know a certain amount and once you've read that book, you progressed the next book. I'm speaking figuratively, but it does feel that way often times and it's a very clear progression and you master this book and then you move on to the next and everybody knows what the what that book in each level means. But what is very true in in sort of technology silicon valley and particularly at square, is like it's not about the book, it's about how well you're able to solve problems, think through problems and work together with other people. Like people skills are really paramount in sort of moving to the next level, and so that's been really neat to see progression go from being hyper rigid to a little bit more fluid but also very empowering. Yeah, when you talk about people skills, what do you find is the single biggest piece of advice you're giving to people that you interact with or work with on the most important people skill or how to develop a people skill? What is what is the tactical or the specific piece of insight that you find yourself delivering over and over again? That may not be obvious to people as they're coming up in their career. That's a tough one, Sam. Why you ask me so much to pause? I'm sorry. I give Um, I don't know what people skills I think that's something that you sort of adapt to over time. On the people's side, and advice that I give, not only the individual sales people but also to my my directs, like my regional managers, and also the managers underneath them, is to seek first to understand before being understood. I mean that's the that's like sales one hundred and one right there, like really understand where someone is coming from before offering an answer. It also ties back to Simon Senex, like be the last to speak. That's just another way of saying be a better listener, but that is I can't tell you how many times I've I've sought to speak first and like really misread what the person needed from me, and so that is my best advice on people skills. For sure's like make sure that you understand the room you're walking into, the intentions of the of the people that you're interacting with. What really matters to your customer? And then, similarly, in getting in getting shit done, a square like what really matters to my partner? What do...

...they want out of this? What is their goal like literally, what is their KPI and objectives and key results and as well as what's their sort of macro level goal? How do I want them to look in the organization? And then, you know, life mottos or guiding principles that I've shared as well as like this also sort of speaks to career progression. Is a Lincoln's quote. Whatever you are, be a good one. That's that's like the concentric circle theory, right, like be good at what the center of the circle is, and then you could be all these other things on top of it. And then, you know, be in the role that you're in. Don't don't be in a hurry. The best way to get to the next role is to be greater than when you're currently holding. And then the the second sort of piece of life advice was someone gave this to me when I was a first an AE in banking and every day was uncomfortable. Easily for the first six months I was like yelled at by by business owners complaining that their rates had gone up or that the banquet closed their alone down. It was really tough. And someone said to me at the time, my manager at the time, and I'll I can talk about her a little bit later, but she said that your comfort zone was once an unknown frontier. She told me that one day this will be comfortable for you and you won't feel anxious or nervous about having conversations like this, and she's right and I think we should all be appreciative of like looking back on our careers, on what at one point was extremely uncomfortable and new and what is totally normal to us today. I think that can be very empowering. I agree. I've got time for a few more questions. One of the things I want to ask you about I know that parenting has said a being a big impact on you. Talk to us about the impact that it's had a specifically in your sales career and what the relationship, from your perspective, is between being a great parent and being a great salesperson and a great sales leader. I don't know about great parent. I'm saying you're a great parent. I'm good by so a little background on that is I have two boys. There are ages two and almost five right now. So they're they're extremely low Roli today. They're like high care, low, low payback right, believable, I allow the fortunately they're too young to listen to this right now. So one day I'm a W payback period. Guys, like eighteen years exactly, possibly twenty two, yeah, but I overall, I will say, though, I think that being a parent has made me a much better salesperson and a leader, and I know that it's funny. I'll talk a little bit more about it in a sect, but like, people don't talk about being parents in technology. They do a lot in banking that it's just something. It's very normal in the culture, but I don't see that a lot here. But why? Why is being a parent made me a better salesperson? I've gotten really good at helping my kids understand where a feeling or resistance is coming from, like really getting to the heart of what's bothering them and then walking them toward a conclusion that solves that issue. That comes from them and not from me. So based on options that I've laid out, like how how do you think you'd like to solve these problems, with these solutions that are in front of you, and when I've just described like that approach. Isn't that? Isn't that a like a consultative sale right there? So having practicing that and having the patients of doing that with my children, I actually has made me much better at at working with with clients and counterparties in business. Also, I don't think it's possible to know just how much you can handle or take on until you're a parent. If you were to tell me ten years ago that I would be doing the job I'm doing today, cooking dinner every night, managing two children, waking up, making the breakfast, making myself food, you know, taking them to school, paying bills, like if I were to do all if you told me that I'd be doing all the things, I would have told you you were fucking crazy. Well, don't you have? I mean you have a partner. You have a partner that helps you with some of those things. Yes, I have an excellent partner that helps me. Okay, good, big that's a big thing. We don't want you doing it on your own? No, but there's a I think there's a Tina fey quote. Could be from her book, but she talks about parenting. Is like every day you do you're doing all of this and you're like this is this is fucking crazy. It's crazy and you do it every day and before you know it you're doing the impossible. And that really stuck with me. Is Like Holy Shit like that that you don't even know what you're capable of until you just you just keep adding, you keep pushing stuff, and I think that's that's really relevant for for sales, for our careers, to know that you're capable of so much. Don't think for a second that you can't do it, because you really just don't know. But Sam, you you've mentioned my partner. I've mentioned in another interview before that I think it's really important for people to choose the right partner that brings...

...out the best in them and he makes a lot of what I do today possible just because of his partnership and I think that's really critical for young people to think about how to I think there was it was either in New York Times or Alawstree Journal article about a year or two ago that said that some of the single greatest accelerants to careers was choice and a partner. I'll find that article. said it to you. I thought it was really interesting. It's so, so true and it's it's difficult, just like choosing a great company is difficult, choosing a great partner's difficult. But when you and I think the other thing that I've discovered is that a lot of these things we are we're getting perhaps a bit off topic, but the act of the selection is is interesting, but it's really what you do with the selection once, once you've made it, because so much about partnership and marriage is about working together and growing together. It's not just about who you were when you went into the marriage. It's about what you're willing to do and who you're willing to become in service of the partnership, not just in service of yourself. That's that's so true. I would say our relationship is evolved a lot, also based on the jobs that we have and how we support each other. Like what is the most meaningful support? And you know, I thought when we were younger the most meaningful support was fun, you know, like really sharing the same interests and doing a lot of things that brought us excitement and joy, for example, like backpacking or hiking. And today, you know, the best way we can serve each other and make us great at our respective jobs and and make our like, make our partnership stronger, is through acts of service for each other, for example, like if he picks up the kids from school, like that makes my life better. Well, yeah, that's so. I know, it's like, yes, it's off topic. Thinking about like is the same thing. In business. Your role will never say the same. You always have to think differently about how you can add value to your customers, to your peers, to the to your directs and how you can serve them. And every year that will change, not only by role but in in terms of the way that the company is evolving around you. And so I think if people are always taking that fluid mindset to all the relationships, personal and professional, it really helps them adapt much faster and also grow much faster in their roles. Yeah, no, that's true. At the same time, I think on the other side, you know the average tenure. This is a talking point I'm like repeating Ad Nauseum out into the world, but the average tender of a commercial executive is now below eighteen months at growth companies. So the point that I'm making is that, and yet, you know, when we're in a marriage, there's obviously ups and downs and you have to work through them in the spirit of a longer term commitment. So there's something about the fact that I think companies and institutions need to make some of those same commitments that we're asking their employees and service providers to make so that we can come together and there's not the sense that if I make one false move I'm going to be fired, I'm going to be terminated, but that it's a long term commitment to to building a partnership and a relationship and that the company is going to try and do for the individual as the individual is trying to do for the company. I totally agree. I think both sides have to be ready to adapt an evolve and that it's interesting you talk about is as a bit of a social contract there that there has to be trust in both ways. That's also why it at the very beginning when we talked about the traits that a leadership team brings to the table, one of them was trust. Like there has to be a mutual trust that I've got you, I'm here to help develop you and help you grow as an employee and similarly, the employee also has to be ready and to bring a growth mindset to the table and be ready to evolve. So there is a there is a contract. Sometimes it's unspoken, but I think the best companies do a really great job at creating that that mutual understanding of growth. Yeah, this has been a great conversation, Ashley. So, first of all, thank you. We have we're past our normal time, but that's okay. We want to leave some time to pay it forward a little bit and talk about some of the folks that have influenced you. So, when you think about great leaders out there in the world that are either mentors to you or people that you respect, or even books that you've read, you know, if we want to follow the bread crumb trail and understand who are the people that create, that helped create and forge the wonderful Ashley Grek, who are those people and you know, just tell us about who they are. Sounds good. Let's see. Mentors. I'll start with mentors. There's some incredible women in payments. That runs some either very large or high growth teams. Angela Martin at Chase Payment Tech. She's head of North America. She runs an organization of hundreds of reps across America and only serving the small business segment. She was the one that told me about my comfort zone and that being sort of fluid and growing over time. And Jennifer Ober Parker, she's the crow at we pay. I find that when I need an unvarnished dancer about the difficulty of something that they've experienced with that I'm...

...experiencing, I get a much clearer and more honest answer on just on the how and not just the what. I think there's an honesty there that in an acknowledgement that, like some some shit is really hard and this is how I got through it, rather than sort of dismissing it as being like, oh, that's just that's just part for the course, just move through it. So I get some really good, unvarnished dancers from them. I also I don't really follow founders or investors closely, but there are certainly like founders that I like to hear from in podcast and interviews, the likes of Elon Musk, Peter Til Reid, Hoffman, which, as I'm naming them, I realize now that it's the paypal Mafia. So likely a second. But in terms of personal relatability and admiration, I think very highly of Levi King, who's the CEO of navcom. It's a business credit platform. So having been in the small business lending space and banking space, I really admire what Dav does. It's also abundantly clear from knowing Levi that he always does what's right. Credit can be a kind of a dodgy business. There are a lot of sort of high interest lenders out there, a micro lenders, and Leavi and his team make sure that everything they do is in the best interests of small businesses that are looking for credit, and that's important to me in working at a company that offers credit and having worked it chase before for so long. It's hard to do and he does it. And on a side note, he has an amazing family and a wife and six daughters. Wow, so Jesus I have I can't even express how much admiration I have for the shit he gets done every day. That's how that's awesome. Leavi King. Yes, leaviking, you asked about you know books or podcasts. I listen to audio books on my way to work. I like to walk to work because I don't otherwise get opportunities to, you know, clear my head or get a lot of exercise. But I also really enjoy, other than the sales huck care podcast, the HPR idea cast is really entertaining to me because it covers a broad range of topics. Planet money is really fun because it's like this is how the world works, and they managed to make economics really interesting. And then, of course, masters of scale, because who doesn't love a good story about companies that we know and love already? So those have been both entertaining and incredibly educational for me. Great stuff, Ashley. If folks are listening, maybe they want to work for you, maybe they want to work with you, or maybe they just want to seek some advice. Is it okay if they reach out to you, and what is your preferred method of communication? Sure, I would love for people to reach out. I am mostly available on Linkedin and you'll find me as Ashley Handsome Crec on Linkedin and it's Greg Grech. If you're out there listening, Ashley, thanks so much for being on the show. CONGRATS on building an incredible team at square and we'll talk to you soon. Thank you, Sam, thanks for having me. Pay Folks, it's SAM's corner. This is Sam Jacob's, your host, founder of revenue collective but, more importantly, host of this year podcast, and we had a great conversation with Ashley Grek. She walked us through a number of different concepts that I think are important, but I think one of the most important is that the keys to leadership, as Simon Sine says, start with why? The keys to leadership are a set of principles that can guide your interactions with people, and Ashley has a well developed set of principles that she uses to inform the conversation that she has with both her peers on the executive team at square as well as the people that she works with, and a lot of those relate to trust and accountability and positivity, and so I think that, you know, that word accountability jumps up time and time again, but it's so important because if somebody can take ownership and responsibility for their outcomes and if they can do so with a positive attitude, I think that's really, really transformative. Another thing that you pointed out is that this concept of fill the space right. So what she's saying is they're these concentric circles. The first is be really really good at what we ask you to do. You really really good at the job description. Be Really, really good at your job. But once you've mastered that, you can begin to expand your spheres of influence. And if you see a problem in an organization, you know it's, as we say, ask for forgiveness, not for permission. Go out and beat, as they say a change agent. Right, go out there and try to fix that problem. If you notice a problem, you know, we've talked about and I talked about with a lot of the people that I that I work with, on the worst side of the spectrum, as you see a problem and you do nothing about it. The second thing that's next worse, right, or maybe next better, is you see a problem and you just comment on the existence of the problem. Not Super Interesting. The third is maybe you see the problem and you comment on the existence the problem to your boss. Again, not very helpful. Right. Number four is you see a problem and you make a series of suggestions and you make those suggestions to your boss.

Now we're getting somewhere. And finally, the most helpful. In my opinion, some organizations aren't like this. You see a problem, you make a series of suggestions to yourself, you begin to you present the basically, you you go to your boss and you say, I'm going to execute these things, unless you tell me know otherwise. I'm going to do this plan, execute this plan, and I'll come back to you with the results of my of my plan around fixing whatever problem may be, and I will come to you and present you that data and we can talk about what it means, unless you tell me not to right now. So I think that is sort of the the the platonic ideal of what identifying and fixing opportunities and gaps within an organization are. Instead of just commenting on the existence of the problem, look for opportunities where you can present a plan, present perhaps the ability to single autonomously or singlehandedly execute that plan and then present the results back to your boss. She talked about that. That's the concept of filling the space. That's what she talks about. So, at any rate, it was a great conversation and we loved having her. If you want to reach out to be you can. I'm on linkedincom forward, slash the word in and then forward Sam f Jacobs. We want to thank our sponsors as always. First a show pad. Show pad as a leading sales enablement platform for the modern seller. And our second sponsor is outreach. Please do share this podcast with your friends, please to tell people, maybe make a post or something on Linkedin. We're trying to build the audience and the more people that are sharing the insights that they get from the podcast, the more successful will be in continuing to get great guests like Ashley. So thanks for listening. I will talk to you soon. See you next time.

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