Welcome back to episode five of Sales Leaders Spotlight. If it's your first time listening, in this podcast series we speak with key players who are sharing their experiences and insights on the current sales landscape.

In this episode of Sales Leader Spotlight, Joseph Fung and Mark Bergen chat about navigating large growth within the Shopify Plus sales organization and the importance of nurturing the sales culture through celebrating merchant’s success stories.  Mark Bergen is Head of Revenue at Shopify Plus.  

Born out of Shopify — the world’s fastest growing commerce platform, which is home to over 500,000 merchants, Shopify Plus powers over 3,600 high-growth merchants across the globe giving them a customizable solution without the need for large investments.  

Check it out below!

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Joseph Fung: Thanks so much for sitting down with us. You've had such a great career in sales in so many different worlds, we'd love to share a little bit about your journey. How did you land at Shopify?

Mark Bergen: I stumbled into sales, way back when and was never really intentional about my thought of becoming a sales leader. It wasn't until I was in my early 30s with Vision Critical that I had a mentor that I looked up to and thought, "Maybe this is a career I want to get into."

So Vision Critical was a great run. I did ten years there and that taught me a lot about sales leadership and developing teams globally. When I left them in August of 2015, I specifically took six months off to meet my kids again (a joke) after a lot of international growth and travel. My wife went back to grad school and while I was looking around on the street, I actually got a call from a recruiter who was looking on behalf of Shopify Plus. My first reaction was, "No, no, no, you're a public company. You're big, I want to find the next company that's gonna be Shopify, not you guys." They said, "No, come down to Kitchener, have a look over. It's really interesting this Shopify Plus thing."

So I came down and had a look at it and it was basically this amazingly scrappy upstart, surrounded by Shopify, which is arguably one of Canada's best and top companies. So, at the end of the day I looked and thought, "I'd be an idiot if I walked from this thing. I’ve got to give this a go." And that was the journey into it.

Joseph Fung: You gave this fantastic talk a couple of months ago on destruction and the changes in retail. I'd love to hear how you're leveraging those larger destructive trends to grow your organization and your sales.

Mark Bergen: Yeah, it's interesting because we’ve grown. I mean Shopify has very much taken over and really dominated and changed the landscape of online commerce.  By offering a saas platform, which is easy to digest. Immensely secure and scalable, and just easy to use. I think in sales we should emulate. We should be easy to buy from. We should have a lot of empathy for the people we're selling to. We shouldn't make this complicated.

And so, really on our side, we spent a lot of time looking at our sales processes, people we're talking to, how we're approaching them, the messaging, everything from the first the email you may send or the first thought, "What does their contract look like? What are we actually asking them to contract and why? And are we actually making this easy for them and helping them better their business and make it easy to buy?" So, it's been interesting looking at what we do in commerce and translating it into how we actually sell and how we deal with our merchants.

Joseph Fung: So, thinking about that, that's a very detailed set of actions and decisions. And it's a contrast to an entirely kinda self-service sale, which Shopify came from.

Mark Bergen: Yes.

Joseph Fung: So, what's that like building out such a sophisticated sales organization so comparatively late in a company's life?

Mark Bergen: Yeah. It's been interesting I'll say that. On one side there's been a lot of trust building that we had do within Shopify. That I had to do, that, "Hey. This is a new way of going to the market." And I think Shopify has done such a wonderful job building an amazing brand in the market space. It really stands for something.  It stands for making commerce better. I had to go and meet some people in the organization and help create trust that was, you know... “We will take care of that brand and we'll continue that brand forward in what we do.”

On the flip side of that, “I get to build a sales organization in Shopify?”  Which has probably one of the largest, strongest brands in our space out there, who has amazing technology, an incredible technology stack. And so, there's a lot of things when you spend your life building companies you are always struggling to get enough resources or attention or build things. I'm blessed on the other side, which is I have this wonderful machine called Shopify and this incredible brand and this incredible brand awareness and marketing and all of those things I can leverage for the growth of Plus. It's been wonderful.

Joseph Fung: That's incredible.

Mark Bergen: I highly recommend it!

Joseph Fung: You touched on the key word there, growth.

Mark Bergen: Yeah.

Joseph Fung: And we talked to a lot of our customers and our partners and sales leaders and how they manage growth. You're publicly traded, so I won't ask about the plans or the forecasts, but what does recent growth look like for you guys? Especially in your organization.

Mark Bergen: Yeah. It's frantic. It's fun. I think it's fairly well known we Shopify Pluses are entering our fifth year right now. We have over thirty-six hundred large merchants right now on the platform. Which, started from a standing start, is a pretty remarkable achievement in a pretty short period of time. For us growth is, you know, we're living in a world of always hiring. Always looking for interesting talent. So there's the obvious growth challenges you'd expect with that, where do you find talent and recruit and train, etc. But also just as the business and the market around us matures, and as Shopify Plus matures and our offering matures and the market changes with technology, with frankly just the adoption of e-commerce more broadly across the globe.  Even the way we go to market and build sales teams and think about how we want to approach the market continues to change. And so, it's interesting. I feel like every six months, the sales model we've built needs to be adjusted or re-thought out again or we need to add a dimension to it. Just given the growth and the way the market changes around us.

Joseph Fung: Not just the rapid growth, but the rapid change that you talk about makes the people side of things really, really difficult. What are the things that you really pay attention to when you think about attracting all those salespeople and growing and nurturing that sales talent?

Mark Bergen: When you look at acquiring talent, it's been interesting, the sales team we have, like a lot of Saas based technology companies is younger. And what I've found is that culture is very important to them and understanding where they want to take their career and investing in them is important. Yes, there's obviously a lot of time we spend just out in the market space talking to people, trying to attract talent, make them aware who Shopify Plus is and what our model is.

But internally we spent a lot of time on culture. I'm very focused on, you know,  “Do people feel like they have a home? Do they feel like they're learning?  Are they developing? Are we investing in the right ways in them?” And for some of the people coming in this may not be their place and that's okay. For those people that come in and they work hard, they try sales and decide it's not right for them, we think, where can we put them? How else can we use them in the business and can we ensure that we have a nice path out of sales perhaps into other areas of the business? And likewise, we have other areas around Shopify and Plus where we're constantly talking to other organizations or people who may be interested in trying sales. And can actually help create a nice path for them into sales and invest in them and see whether or not it's a career they want to take. Because as you and I well know, it's a great career.

Joseph Fung: So, Shopify Plus is five years in, and for a lot of startups while they're in their fifth year, culture still means staying late, maybe after work parties and beer in the fridge. You can see just from the office here that there's so much more than that. When you think about designing that culture, nurturing it, what are the things you guys really hang your hats on?

Mark Bergen: One of the things I actually love about this company is from the top leadership right down, there's a real sense that we commerce better. If we're not making a merchant's life better, then we're not doing the right things. One of the things we set out right from the get-go was to say, "Yeah, we wanna win. We wanna be big and bad and be the best sales organization that we can, but we're gonna do it by delivering the best merchant experience possible."

Yes, of course, we celebrate numbers. We've got aggressive targets. We do a lot of the usual things you'd expect, but we actually spend a lot of time talking to merchants and celebrating merchants and celebrating our merchants success stories and inviting them to come in and actually talk to our sales team. We send our sales team out to talk to them. We do lots of events with our partners that are focused around celebrating success. And so, I find those things are important because it actually creates more of an attachment to the work that's being done here beyond simply getting a paycheck. It's a paycheck, there's another paycheck down the road and now I have to play that game and I don't want to. I'd much rather play, "Hey, we're actually making a difference in people's lives and we get out and you hear the stories of some of the merchants we work with, it's stunning and inspiring.

Joseph Fung: That's awesome.

Mark Bergen: Yeah, it's really amazing.

Joseph Fung: That must make it very easy to attract sales people because they're talking those wonderful customers, but you also dropped that comment about giving people the opportunity from other areas of the organization to move into sales. What would be a common source? What would be a common path for someone into the sales organization?

Mark Bergen: It's interesting. What I found, I'll diverge a little bit off here…  It's interesting, you meet a lot of sales people and you talk about, "Hey, what was your path into sales."  There's very few who have this nice, great linear path. "You know, I woke up one day and decided sales was my career. I went into school for sales and here I am now ten years later being a salesperson." Most people kinda accidentally kind of jumped and bounced into sales. Because I think in a lot of cases we don't take it seriously yet as a career I think often in society — at the educational level.

When you look at what makes great salespeople, drive and dedication, competitiveness, empathy, curiosity, care for others, all of those components exist all over the place. And I find that there's a lot of people that, in the organization, maybe in a support role, maybe it's a safer place in marketing experimenting and understanding what value propositions mean, etc. But they think, “that sales thing is kind of interesting and I'd like a chance to try that.”

So I like to create opportunities for people that come over and say, "Sure. Let's give it whirl. Try it out. If it doesn't work, no problem, I totally understand. That's okay." And we've done that, and we've seen some wonderful salespeople come out of it. Come out of our support organization. Come out of marketing. Come out of other areas.

Joseph Fung: That's fantastic. Giving people that opportunity to really grow and flourish, it must be so rewarding and just fosters great loyalty as well, I think.

Mark Bergen: It does. The other thing, frankly on a complete self-serving side, the more people who understand sales and are empathetic to it, the better. I had great story. I had saleswoman who is actually still in the business, and a year and a half ago she raised a hand and said, "You know what, I'm teaching this stuff and I'm not really sure I get it. I'd like to join the sales organization."

Joseph Fung: Wow. That's awesome.

Mark Bergen: Yeah. Crazy! So she joined, she said, "I'll give you a quarter." She carried a bag and we treated her like every other salesperson. She had to give updates, had to build a pipeline, etc. and she ended up closing a few deals. And she came out of it at the end of it and she looked and said, "Oh shit! Guys, I thought I knew what I was talking about... I actually didn't know" Her level of understanding, her empathy, her ability to relate salespeople when it comes to teaching content is now, night and day.

Joseph Fung: So is it fair to say that you endorse the idea of sales and professionals spending time initiating sales?

Mark Bergen: Hundred percent. In marketing, in support, and finance... absolutely.

Joseph Fung: I love your comment. You said that, "The more people who know what it's like to sell, the better it is for the company." You talk about giving people that opportunity to join sales, and go back into other areas. Where are some of the places that your reps have landed?

Mark Bergen: So for us, we've actually had a whole variety of areas.  One of the nice things... one of the luxuries within Shopify and Shopify Plus, is we're just a rapidly growing business. So, a business unit that didn't exist six months ago, exists today and we need people to go in and see it.  I've had people that have moved internationally and started to help out opening different areas of the organization, move into solution engineering, move into support roles, move into merchant success roles. So we've had salespeople move into lots of tangential areas around the business, either because of expansion,  there's need and they have real interest in it or they want try it out for a few years or it's an interesting move for them because of new divisions and new areas of the business opening up and we need to seed them with people who understand how to sell.

Joseph Fung: Shopify Plus is a more complex product than your Shopify offering. That comes with many integrations and offerings. How do you approach training your salespeople to help them be more effective with such a complex product?

Mark Bergen: That's a great question and in fact, we came into this year realizing that often with a business that grows this quickly, sales managers and sales coaches often get forgotten. We spend a lot of time focused on the reps, but we sometimes forget that a lot of coaches and managers used to be direct contributors. Now they're put into a management position and actually that's a fundamentally different job. They're often poorly supported and so internally this year we've named it, "Year of the Coach." We're spending a lot of time with our coaches helping them be more effective coaches and managers to their reps.

For us, when we bring reps in, we go through a two week, full intensive.  They go through a complete onboarding, right from the Shopify culture values, through to Plus, why we exist, competitive positioning, value propositioning, all of that stuff. Then they start their integration into the actual sales world. There's some job training that goes with it and we kinda build them up and that continues for about four months. But they'll continue to come back out of the field, they'll come back in for ongoing coaching, ongoing teaching, they'll do some job shadowing along the way, they'll work with our solution engineering, they'll work with our support organizations so they get a more rounded view of the business. But we will look and say, "We don't have a rep that we're really confident to say yeah, they're ramped until we get to like month six."

Joseph Fung: Okay. So with a lot of organizations, they struggle with how they manage variable compensation and targets with that [crosstalk 00:13:26] and their often in tension, these two different motivations. How do you balance those.

Mark Bergen: I think for reps, and it's a reality of the work, which is in many cases we're variable based paid people. There's a pay for the performance side of the business and so we have reps that want to get out of the business. It think most what we see is you know, the reps that are hungry will accelerate through it fairly quickly. And, when they're going through that four-month process, they are performing absolutely — the role of sales. It's just that we're continuing to give extra coaching, extra support. We are pulling them out of the field to continue to do some upscaling with them.

The people who have a long-term view of sales, and the people that we actually really like to invest in, they get it. They know. I will take four or five a week right now in the classroom because in four or five months, I'll be that much better for it. Then everybody, to some degree, has their own speed through it. So we see people who'll be closing deals within months of joining, some will be slower ramp into it, but we find if we invest the right amount of effort up-front you're way better for it in the long run.

Joseph Fung: You eluded also to the idea of having a self-service commerce origin that changed the way you thought about crafting your sales journeys and customer journeys. Is there anything specific that comes to mind when you think about how you might be selling differently?

Mark Bergen: Not that there's anything revolutionarily unique in what we're doing. We do a lot of experimentation internally. I'm very interested in new techniques around AI, around enablement, around business operations and lead scoring and finding better ways of assessing where we should spend time and eliminating things that we shouldn't be doing that are just not fruitful uses of time. But I think long term, when I look at scaling businesses, what eats away at me a little bit is, in a linear way we're a very human-centric business. I need to add X number of deals next year, therefore, I need to increase headcount by Y. And that's a standard every sales manager, every VP of Sales will go through that every single year as they try to work on their forecast for the next year. I'd actually love to get a world where it's like, "I need to grow by X, therefore I don't need any new people this year." Or I figured out how to do a self-service model or 50% of the sales process happens through a buyer center and they need to engage with us only for the last contracting component or similar.

So those are the pieces that kinda consume me a lot more right now. And, doing experimentation around that. How will we get just that much faster. And not necessarily to remove the human element, but to make the human element that much more efficient.

Joseph Fung: So when you think about the human elements, one of the things that we hear is a need to have for an enterprise sales rep to be successful at Shopify, is to have “Energy and a wicked worth ethic. That sales is a 24/7, 365 operation.” What does that mean for you guys?

Mark Bergen: Yeah for us there's a reality of it which is, you know, sales is a difficult profession. We know that. There's absolutely a side of sales which is... “we have quarterly numbers, we have monthly deliverables and they're measured very cleanly, very accurately and they're put on a board for everybody to see.”  And that's intimidating for a lot of people and that's the nature of sales. So, I'm not going to pretend that doesn't exist, it exists. Welcome to sales.

The difference that they give it is, I see in a lot of salespeople there's a real stark difference between “sales is my job, and sales is my career”. We're always looking for the A player. Every organization wants A players and the reality is is that it doesn't happen. With a lot of people who are really good salespeople, and the handful of people who are just unbelievable salespeople and we all want to emulate them, we want to pay them well, we want to retain them at all costs and we'll fight tooth and nail to bring you into the organization. And I think that part of it is that job versus career. So I see salespeople who'll come in, they're happy, work hard, they'll put in their nine to five, maybe even eight to six. They'll do what needs to be done, but then they're done and then they're checked out, “thanks very much.” Versus sales career, where you can just... you see the difference. The ones the come in you know... on a Sunday night you're getting a note saying, "Hey, I was just reading this book. How do you think this applies." Or, you know, “On my time studying the Challenger sale, or Sandler. I just heard spin. What do you think about it?” Or they're reading a Forbes article and they have a new idea on how we perhaps could take advantage of new technology systems. Those are the people that I think are just amazing.

And so, to a degree about putting stuff like that out, yeah, we're trying to self-select a little it into... you know, I'd love to find those people who come in and say, "Sales is my career. I love sales. I'm passionate about sales. I love what I do and I live it and I'm going to be the best I can be at it." Those people are amazing.

Joseph Fung: You know, when you think about taking people like that and giving them the rights tools and getting out of their way, in many ways Shopify has been so successful because they've automated a lot of routine processes in commerce, what do you think about it? What do you think about when you think about automating areas of the workforce and giving those high performing sales reps better tools and more efficient opportunities?

Mark Bergen: Absolutely. We have to. Sales is very labour driven. It's a human-centered activity. It's a costly activity in most organizations and there's a lot of variability to it. Why is sales hard? Sales is hard for a lot of reasons, but one of them is at the end of the day you don't make the decision whether or not the person buys. You are wholly dependent upon someone else to make a decision and that makes it very difficult. So I think anywhere we can help reps and we can help the organization to spend time, where we're wasting time... common questions, common answers. I've never worked in an organization that doesn't have a problem with knowledge management.

I've never worked in an organization where the same damn question is asked every four weeks by the new person on, saying, "Hey. Do we have a case study about X? Hey, what's the pricing for Y? Hey, doesn't anybody know does this integrate with us?" They're common questions in the organization so we need do find new ways to surface that in a more intelligent, thoughtful manner and start breaking some of these just cycles we get into. How do we lead score more effectively? How do I ensure that when you make that call because I say this is the right one to call, that we are 95% certain that this is the right person to call, and not 9.5% certain it's the right person to call.

Joseph Fung: Get those right answers first time, every time.

Mark Bergen: Absolutely.

Joseph Fung: So a couple of quick questions and then we'll let you go. Thanks again for the time.

Mark Bergen: Sure.

Joseph Fung: I love hearing how you think about these systems and the patterns in your organization. When you think about those managers who are working day to day, with their front line reps, and they're now looking at moving in their career. You know the wanna try to look at things more systematically or more broadly. What advice do you have for a sales manager that's looking at taking that next step up?

Mark Bergen: It's interesting, we've been talking a lot internally within Shopify actually, and within Plus, about how we support the growth of leaders. Because it's a very difficult job and it's one that there's a lot of great books on how to be a leader, it's actually hard in practice. A lot of the things that we're trained how to do, which is kinda that frontline job, we get really good at a craft and now we have to move to pupil management. Or, the question you're asking, "Now I need to go from managing the front line people, which at least I understand the craft, now I gotta be a leader of leaders. What does that look like?" And that's very difficult to do.

So I think for a lot of people there's a lot of changes that go into it and I think as you continue to move up in organizations, the breadth of the vision you have for the organization changes drastically. You move from dealing with, "I'm an individual closing these many deals, to running a team closing these many deals times seven, to I now have to run an organization and think about that shape of that thing that looks like next year and we continue to develop it." So, I would say that that's one.

Number two, get close to numbers. Make numbers your friend. Most businesses are very tied to numbers. If they're not tied to numbers, go find a CFO and they will tie you to the numbers very, very quickly. If you're tied to numbers, you'll have a very difficult time with it, so get close to numbers and better yet find someone who understands numbers really, really well.

And the other one I learned, and I still think I'm learning to some degree, is there's this sense I think with a lot of leaders that you're kind of alone. That your have to do it yourself. I think some of the best managers are those, and some of the best leaders are those that actually recognize they don't have to do it themselves. But, I actually know the person you should talk to because they're better at this. One of the best mentors I had in my career was that guy. He was just fantastic at ensuring he didn't have to have the answer, but he knew who did have the answer, and he was happy to make a warm introduction to get the answer.

Joseph Fung: That's fantastic. One last closing question.

Mark Bergen: Sure.

Joseph Fung: I know I promised I wouldn't ask questions about Shopify's plans. But what about your plans? You've got this remarkable opportunity, these really wicked challenges, what are the juicy problems that you're working on next?

Mark Bergen: One of the appealing parts of Shopify and Shopify Plus, it's one of the reasons I stepped back in 2015, it made so much sense to sign with these guys and to come on board and to help build this thing out.  It was the vision they gave was, "We don't want to do things like everybody else. We're determined to a hundred year business. We know how to be a thirty-year business..." Because there are all kinds of businesses that are ten, twenty, thirty-year businesses, but there's not a lot of hundred year businesses. Part of the challenge that the organization has given to all of us in leadership positions, and I have in sales, is don't just do it the way everybody else did it just 'cause. Explore, experiment, try to find new ways, break stuff, see what happens. So, there's lots of dimensions to that as we've continued to grow. We've touched on few through this podcast in this conversation. And so, clearly, there's a lot of interesting things there. I've mentioned kinda playing with AI and finding more interesting ways of bringing intelligence to the organization.

The second one is just elevating sales as a craft I think. As I mentioned earlier, there's a lot of people who kind of — fall into sales. Not many who deliberately come into sales. So, I have a bit of a side mandate within Shopify Plus of helping our region help raise the profile of sales within the region. Working with universities. Helping professors who are thinking about adding sales into their curriculum. Helping them think about what that could look like and help to promote that. I think for all of us to continue to grow we need really, really great recruits coming into sales who understand what an amazing career it is. But one of the big juicy problems is figuring out how to continue to do that.

Joseph Fung: Well in terms of elevating the craft, I mean even just the insights that come and shared today have been absolutely incredible. Thank you. Thank you so much, Mark, for spending the time with us.

Mark Bergen: Thank you. It's been interesting. I appreciate it.

Thank you for tuning into this episode of Sales Leaders Spotlight.

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