PODCAST 57: Career Progression as a Concentric Circle to Become Top Manager w/ Ashley Grech

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.

If you missed episode 56, check it out here: PODCAST 56: Drafting an ABM Strategy That Works w/Alon Waks

What You’ll Learn

  • What Square sells (it’s more than a square!)
  • How the journey to becoming a manager varies by industry
  • How to get into a creative mindset
  • Training investments you must make
  • How to break your sales team into three “pieces”

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Show Agenda and Timestamps

  1. Show Introduction [00:00]
  2. About Ashley Grech: An Introduction [01:47]
  3. Mother of Dragons, Manager of Managers [11:17]
  4. The Creative Mindset [13:47]
  5. Your Career as Concentric Circles [20:59]
  6. Diversity for the Bottom Line [23:38]
  7. Parenthood as Proving Ground [36:33]
  8. Influences [43:56]
  9. Sam’s Corner [48:10]

Show Introduction

Sam Jacobs: Hey, everybody. It’s Sam Jacobs. Welcome to the Sales Hacker Podcast. We’re so excited. This week we’ve got Ashley Grech, the global Head of Sales for Square. Square is a $30 billion market cap company that is an all encompassing payments and commerce business that serves the small and medium sized businesses of the world. Ashley is an incredibly impressive executive and leader and we’re so excited to have her on the show.

We have to thank our sponsors. Our first is Showpad. Showpad is the leading sales enablement platform for the modern seller. It’s the industry’s only unified sales enablement platform combining sales content, training, and coaching conversations. It’s a one-stop shop for your sales team to prep and deliver the best buying experience for your clients and it integrates with your core sales and marketing systems such as Salesforce, Microsoft Dynamics, Outreach, Marquetto, G Suite, Outlook, etc.

Our second sponsor is the leading sales engagement platform, Outreach.io. 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 has your back now.

About Ashley Grech: An Introduction

Sam Jacobs: Ashley Grech is the current Head of Sales at Square. She’s leading a global team and she’s going to talk about how she’s building that team and how important process is to the development of that team. Ashley, welcome to the show.

Ashley Grech: Thank you, Sam.

Sam Jacobs: What is Square?

Ashley Grech: We’re best known for being a point of sale company. Once upon a time, we were the little white reader that came in and changed the payments market. Square has evolved into a full scale commerce platform. It’s currently around $2 billion in revenue, $30 billion in market cap.

Sam Jacobs: Tell us about your sales organization.

Ashley Grech: It’s just under 200 people in a number of different functions. We call ourselves a commerce platform. The monetary exchange is the crux of the relationship, but we sell the ability to take payment, the hardware on which to take payment, the background 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 small business capital, which is pretty incredible to see a multi-location business be able to fund inventory or fund the expansion of their business through Square. We sell appointments, marketing services, loyalty tracking. For larger corporations, we have our API and SDK suite for them to be able to build the experiences they want.

It’s about interacting with your customers, using marketing and loyalty to bring them back, and then also tracking that type of behavior.

Sam Jacobs: Tell us about your background, and how that led you to Square.

Ashley Grech: I spent almost 13 years in banking. I joined small business sales in 2007 during the financial crisis. It was the toughest education. It taught me so much about understanding the perspective of the customer and the product.

Then I went on to enterprise because it felt like the next frontier of a skill that I wanted to learn. That was exciting because in the Silicon Valley there are a ton of fast-growing companies with needs that evolve every month.

Manager of Managers

Sam Jacobs: You moved from being a manager to being a manager of managers. What are the key skills that are different?

Ashley Grech: One of the toughest transitions was the strength of my communication skills. You have to work through people, coaching them to see something on their own, and find their own words that feel true to them.

I spend at least the first half of any one on one with my regional managers or regional leads talking about people because through that and situational coaching, I can help them brainstorm, think through problems, see the bigger picture. Most of the challenges of management or leadership is people.

It takes 100 different forms every day and you rarely see the same thing twice, so you walk through it together. It builds trust between me and my managers and between them and their directs and allows them to handle it their own way without me.

RELATED: How To Be A Great Sales Manager: 10 Essential Qualities For Success

The Creative Mindset

Sam Jacobs: Do you have a set of principles that guide you?

Ashley Grech: I believe in a creative mindset, not a deficit mindset. I call myself a recovering perfectionist. That implies that something is below zero, but if you’re always getting back to zero, you’re not getting ahead.

First is to set the vision for the organization, and we do have a sales vision on what we want to be as an org and as our contribution to the company.

The second thing to think about is, who are we as leaders to get us to that place? We’re currently a $30 billion company today. If we were to say, “We are the sales leadership team for $100 billion company,” what would that mean on the street?

We work backwards from there and talk about the type of person or credo we want to bring to each and every one of our reps. We do have a couple of themes that we rest on and that we really try to bring to every interaction with our reps. One is a positive energy. Bringing positivity every day and showing people that sales is hard, but we’re a happy bunch. The second is that we are appreciative of what we have. I often say that I would not choose any other problems. I am accountable, which is the third one. I’m accountable to my team, I’m accountable to our executive team. If you take ownership of what you do every day, then your team trusts you to make the best decisions for them, and they trust that you have their best outcomes in mind. The fourth is trust. We want to be trusted, we want to trust each other because that sort of trust and transparency is incredibly important in the grander scheme of change management and being in an organization that evolves daily. Then finally, our team trusts us to be visionaries, to see around corners that they don’t see.

Your Career as Concentric Circles

Sam Jacobs: One of the concepts that you’ve talked about in the past is career progression as a series of concentric circles.

Ashley Grech: I get a lot of questions like, “How can I grow? What can I do next? How can I continue to push myself?” I draw a series of concentric circles and I talk about that as their career progression plan. It’s also a way of creating explosive change at Square.

The first circle is your job, right? That is your job description. That’s the one that we posted online.

The second concentric circle is how you do it, how you see your team, your peers. If you think of the first circle as you, and the second circle is the people that are immediately around you, how do you make their lives better? How does your team feel about you as a manager? Do you have high morale on your team? Do you create culture with them? That’s the extra credit in the second concentric circle.

The third concentric circle is, what are you doing for the company above and beyond your team? You earn the ability to stretch into the next concentric circle. Where the magic happens is in that third concentric circle where you get this cool Venn diagram effect of overlapping with other outside circles. Those people are also doing cool things for the company, and you can do really cool shit together.

Diversity for the Bottom Line

Sam Jacobs: How do you indoctrinate diversity into the DNA of an organization?

Ashley Grech: Square’s sales team is incredibly diverse. It’s over 50% women. We hire a ton of diverse thought, industry, and ethnicity. But I don’t really want to focus just on gender or ethnicity. It’s not complete.

I want to create a team in which we will never “yes” each other to death because we’re all the same. That is important from a business standpoint.

We serve mostly small business sellers in the US that are incredibly diverse. A small business owner in California will behave very differently than a small business owner in Missouri. We have a sales team in St. Louis and their approach is a little bit different and it works just right.

We try not to hire aggressively from tech companies. Square’s really unusual in that we have a lot of products. We want people who can sell an entire ecosystem. We started hiring out of food and beverage, medical device, or pharmaceutical sales. It’s been really interesting to see the accelerative effect on how quickly those AEs can ramp up when they speak to something they know about.

Small business owners want someone who understands their business. It’s really important as a company to serve every demographic. Having a really diverse team means that we push each other from a career growth and mentorship standpoint. Everyone brings something different to the table.

Parenthood as Proving Ground

Sam Jacobs: Talk about the impact that parenting has had on your sales career.

Ashley Grech: I don’t think it’s possible to know just how much you can handle until you’re a parent. If you told me 10 years ago that I would be doing the job I’m doing today, cooking dinner every night, managing two children, waking up, making them breakfast, making myself food, taking them to school, paying bills, I would have said you were fucking crazy.

I have an excellent partner. It’s really important to choose the partner who brings out the best in you. That’s really critical for young people to think about. One of the single greatest accelerants to careers is choice in a partner. I thought when we were younger, the most meaningful support was sharing the same interests like backpacking or hiking. Today, the best way we can make us great at our jobs and make our partnership stronger is through acts of service for each other. For example, if he picks up the kids from school, that makes my life better.

It’s the same in business. Your role will never stay the same, you always have to think differently about how you can add value to your customers, to your peers, to your directs and how you serve them. Every year that will change not only by role, but in terms of the way that the company is evolving around you. If people are taking that fluid mindset to all of their relationships, personal and professional, it really helps them adapt and grow much faster in their roles.


Sam Jacobs: Tell us about your influencers.

Ashley Grech: Angela Martin at Chase Payment Tech. When I was first starting she told me, “One day this will be comfortable for you and you won’t feel anxious or nervous,” and she’s right. That can be very empowering.

Jennifer Aubert Parker, she’s the CRO at WePay. She gives clear and honest answers. There’s an honesty in the acknowledgement that “some shit is really hard and this is how I got through it” rather than dismissing it.

I think very highly of Levi King who’s the CEO of nav.com. I can’t even express how much admiration I have for the shit he gets done every day.

The HBR IdeaCast is entertaining because it covers a broad range of topics. Planet Money is fun because it’s like this is how the world works and they manage to make economics interesting. Masters of Scale because who doesn’t love a good story about companies that we know and love already?

Sam’s Corner

Sam Jacobs: Hey folks it’s Sam’s corner. We had a great conversation with Ashley Grech. She walked us through a number of different concepts that I think are important.

What We Learned

  • What Square sells (it’s more than a square!)
  • How the journey to becoming a manager varies by industry
  • How to get into a creative mindset
  • Training investments you must make
  • How to break your sales team into three “pieces”

Don’t Miss Episode 58

If you want to reach out to me I’m on LinkedIn. We want to thank our sponsors. As always, Showpad is the leading sales enablement platform for the modern seller, and our second sponsor is Outreach.io.

Please do share this podcast with your friends, visit or make a post on LinkedIn. We’re trying to build the audience. The more people who share the insights that they get from the podcast, the more successful we’ll be in continuing to get great guests like Ashley.

Thanks for listening. See you next time.

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