Everything we’ve learned about scaling sales

In this week’s episode we’ve dug down into the podcast vaults to bring you some of the best insights shared by our guests about scaling sales.

It’s no surprise that one of the key levers for growth as you go from startup to scale-up is your sales team. How quickly you’re able to accelerate growth depends on your ability to build a nimble sales org and develop a strong sales strategy.

But that’s easier said than done, which is why we’ve published our new book Intercom on Sales: a deep dive into the many lessons we’ve learned about how selling works at scale, covering everything from hiring tactics to the needs of modern buyers to fundamental processes for forecasting and managing deals.

We aren’t the first to learn these lessons – in fact, many of our insights are drawn from past conversations with leading sales experts. These conversations have had a huge impact on the way we approach sales within our own company, and we hope their wisdom can provide some insight for other organizations, too.

In today’s episode, we’re featuring some of our favorite advice from those chats. You’ll hear from:

1. Sales trainer and author John Barrows, on hiring sales talent
2. Pipedrive’s SVP of Sales, Tara Bryant, on building a solid sales framework and moving upmarket
3. Stripe’s Head of North America Revenue & Growth, Jeanne DeWitt, on driving growth through customer expansion
4. Our Senior Director of Sales Ops, Jeff Serlin and Director of Demand Generation, Brian Kotlyar, on how sales and marketing should work together to build a single revenue plan

To hear each of these conversations in full, check out episodes of our podcast. You can also subscribe to the show on iTunes, follow us on Spotify or grab the RSS feed in your player of choice. What follows is a lightly edited transcript of the episode.

Hiring for sales with John Barrows

Although salespeople can add plenty of arrows to their quiver over time, there are a few intangibles that can’t be coached: enthusiasm, drive and teachability. Here, LB Harvey, Intercom’s SVP of Sales, and sales trainer John Barrows discuss how to hire top talent for a rapidly growing team.

LB Harvey: What are some of the most important intangible elements or characteristics you look for in top sales folks?

John Barrows: Passion and work ethic. Those are two things you cannot train. I worked with Jack Welch of GE for a couple of months to get his online MBA program off the ground, and when I started my first company way back in the day, Jack came to Boston to do one of his conferences. There were a thousand people in this seminar that he was doing, and it was just Q&A. At that time, my company was 50 employees.

I stood up and I said: “Jack, look. You talk a lot about passion and all this other stuff. When we were five people starting this company, we were all super passionate. Everybody was on the same page. Get to 20 people and everybody’s still super passionate. Now at around the 51st person that we’re bringing in, it just doesn’t seem that they have the same passion that we do for the business. How do you instill your passion on somebody else?”

“I don’t care what you’re passionate about; I care how you describe what you’re passionate about”

In front of a thousand people, he basically told me I was an idiot. He said: “You’re looking at it all wrong. You can’t instill your passion on somebody else. You have to hire passion.”

That flipped my hiring persona upside down. I can teach skills, I can teach technique, I can teach product knowledge, I can teach all that stuff to somebody who’s willing to learn, but I can’t teach drive. I can’t teach passion. I can’t teach grit. Sales is a brutal profession. You literally get told “no” 99 times, and you have to keep coming back asking for more so you can get that one “yes” in 100. That’s why one of my favorite interview questions is, “What are you passionate about?” I don’t care what you’re passionate about; I care how you describe what you’re passionate about.

For instance, if I asked you that question, you could say, “I really like customers, and I really want to do right by them and make sure our product’s a good fit.” Or you could say: “Holy crap. Did you see what happened on Thursday night with the Patriots? They got absolutely smoked. I’m rip-roaring pissed off, but I think it’s a good thing, because you know what? They needed to get knocked down a notch here. I still think they’re going 17-1 this year!” I don’t care if football had nothing to do with what you and I were talking about, if you describe it in a passionate way, that means you have some sort of fire in you. My job as a leader is to take that passion and connect it to my business so that you can bring a fraction of that to the table when you come work for me.

The last one is coachability. You need somebody who is coachable. A leader should still be coachable, but if you’re hiring somebody who’s a little bit lower on the totem pole, you need somebody who’s open and willing and wants feedback. You need somebody with a thick skin and who wants feedback so that they can get better.

Pipedrive’s Tara Bryant on doing more with less

There’s often a temptation to think that hiring salespeople is the answer to beating ever-increasing sales targets. But Tara Bryant, SVP of Sales at Pipedrive, thinks this is a mistake if you don’t have the right processes, systems, and metrics in place first. These lay the foundation that enables your team to run as efficiently as possible. At SaaStr this year, we spoke to her about how she approached scaling the sales team at Pipedrive.

Courtney Chuang: You’ve talked about the need for alignment, but there’s a temptation often just to keep doing more. How do you approach figuring out when to add more salespeople and when to add more tools?

Tara Bryant: It’s funny you ask me that. When I started, they had a big growth plan as far as headcount, but they were a little bit looser on processes and cadences and things like that framework I was talking about. Coming in Q4 to a company is always a bit of a challenge, because obviously you’re ending the year and the quarter, but you’re also trying to plan for the next year, and you don’t really know enough information. So one of the things I did was I took a step back and said: “This is a really aggressive hiring plan for 2019. We’re not going to hire anybody.”

“Unless you’ve got the process in place, and you’ve got a really good framework, you need to really optimize what you have”

We’ve got a great staff right now, and I think a lot of sales people actually make this mistake where they look at the plan, and they say, “Okay, I’ve got to get to X, so I’m just going to hire more people, and that’s how you make your quota.” And I actually don’t believe that. I will always try to hold back on the hiring plans. I’m a process and data person, so unless you’ve got the process in place, and you’ve got a really good framework, you need to really optimize what you have. We have a great sales force. I mean, these people love our customers, and they really want to make sure that they understand the tool, so I think we’ve got things that we can fix first before we look at really scaling it. That’s the number one thing that we’ve done. So again, we got aggressive headcount to see the growth, and we put together a plan where we can actually see maybe even a little bit more growth with the same people.

Look, if in H2 it looks like if we put some gas on this and if we did hire more people, then we could, I’m fine to do that. But we have to make sure that we’ve got this at least dialed down. I mean, it’s a journey. All of these companies were on a journey, it’s not just to say they had one destination. So as we’re going, we’re always going to fine-tune these processes, but again, making sure we’re optimizing what we have. We’re just not there yet, so I don’t want to really grow headcount yet.

Stripe’s Jeanne DeWitt talks driving expansion revenue

If you had one dollar to spend on your startup’s growth, should you spend it on acquiring a new customer or on expanding an existing one? In a recent study of a few thousand SaaS executives by ProfitWell, seven out of 10 of them said if they had to focus on one piece of their business, it would be net-new customer growth. But Jeanne DeWitt, Head of North America Revenue & Growth at Stripe, argues you’re hampering your own success if you don’t make room in your sales strategy to focus on growing existing customers.

Courtney Chuang: What does your structure look like for the expansion side of your business? Because you mentioned that you now do have a distinct Account Manager org.

Jeanne DeWitt: Yeah. We’ve gone through a number of iterations on this one too. Today, it depends on segment, so you have different buying behaviors. Because it’s so core to what Stripe does, we actually have integrated the startup segment, so we have both new business and existing business under the same leader. Separate people focus on new or existing, but there’s a single leader so that we have a really integrated strategy for that segment. The role is focused both on upsell as well as retention and customer success activities. We basically have been very focused on what we think are most likely to be the breakout startups of the future, over-investing in them before they’re technically large enough, spending enough money to merit that.

If they get the best practices from us, does that make them more likely to become a Series B or Series C company because we helped facilitate that? That’s been one aspect. Then also a set of targeted campaigns where we see behavior within an account and realize they might benefit from either an optimization or a new product.

“One of the things that’s great about Stripe’s commercial model is we make money when the customer makes money. Having those together I think works effectively”

In our growth, which you can think of as a Series-B-through-D company segment, we’ve experimented with different models of folks doing just customer success and more commercial activities, and I think are likely to move to a model where those are actually integrated. One of the things that’s great about Stripe’s commercial model is we make money when the customer makes money. Having those together I think works effectively.

Then in our largest accounts – the public companies, the enterprise ones – we’re figuring out exactly the right model there. You’re doing super detailed payment-optimization work with them. If they’re doing billions in payments, basis points matter, so we do a lot of detailed analyses on that front that are more customer success oriented. If you’re doing a renewal, it’s a very complicated process that can be a six-month negotiation, so having someone who’s an expert in that is useful. Then as we’re selling products like Stripe Billing, they might have Homegrown or another subscription product in there, and that can be a complicated sale in and of itself.

What we’re trying to do is ensure that roles are focused enough that you can be an expert, but not create such specialized roles that you wind up with 10 people in an account, which isn’t a great customer experience and isn’t very efficient.

Courtney: We’ve talked a lot about how you’ve evolved the team at Stripe today. Stripe is, I think, now valued at something like $22.5 billion. When you’re growing that rapidly, I imagine that what worked really well one year or even one month ago can start to get strained with that growth. What are the indicators that it’s time to evolve the team?

Jeanne: Yeah. One of the things I really value about Stripe is it’s a very open and transparent company that really expects leadership from everywhere within the company. We engage the teams very heavily in helping us actually understand that.

I would say half of the evolutions we’ve done have been management-driven. More about: “Hey, I’m seeing a certain pattern here. Let’s do a fair amount of analysis and understand the market opportunity in our position within it.” Then we choose to point the team in a certain direction.

“We have all these insanely smart people, but they’re kind of not getting to depth. Clearly, there’s too much breadth here”

An example of that would be that we’re very focused right now on working with SaaS platforms, so Shopify and Squarespace. Those are SaaS companies, but e-commerce is a core part of what they do, so they work closely with Stripe. We’re purposefully having more emphasis on that, because it’s an important segment of the market for us to pursue.

In other cases, it’s been about seeing where either people aren’t getting to the level of depth you want them to and realizing: “Wow. We have all these insanely smart people, but they’re kind of not getting to depth. Clearly, there’s too much breadth here.”

Or we’ve done different things, too, where we’ve surveyed where people are spending time sometimes. One of the big changes we made was that originally Account Executives were in charge of deploying their accounts as well, which is sort of crazy when your product an API. When it got to the point where they were spending more than a third of their time deploying accounts, you are like: “Wait a minute. That’s not how we’re going to grow as fast as possible. Time for a new role.”

We’re on a pace where there’s been a major evolution about every 12 months. Typically, about six months in, we start doing what we call a “dress rehearsal”.

We have an inkling that we want to make this change, and we start experimenting and putting some lightweight structures in place that would migrate us towards where we think we need to evolve. That way, when you finally announce, “Hey, we’re moving segment lines,” or “We’re making this change,” people are kind of like, “Oh. Well, duh.”

Intercom’s Jeff Serlin & Brian Kotlyar on having a singular revenue plan

Sales and marketing tactics can vary, but to succeed, teams need to be aligned around one plan: a revenue plan. If the ownership isn’t shared, finger-pointing creeps in. In this episode, we flipped the script and had our Senior Director of Sales Ops Jeff Serlin and Director of Demand Gen Brian Kotlyar interview each other in a free-flowing conversation about the importance of forming a strong relationship between sales and marketing.

Brian Kotlyar: Jeff, you’ve done sales operations in businesses across the whole spectrum of scale. As companies mature, how do you see the relationship between sales, marketing, and operations changing as they grow and become more complex?

Jeff Serlin: When you start off as a company, you first have to validate that people are willing to give you money for your product. You do this before you even come up with the strategy about what size and what type of companies you want to sell to. In the early days, you’re just trying to acquire customers, figure out why they’re buying, and go get more of them. I don’t know that you need much in the way of sales operations or even a big sales team, as you mentioned. You just need enough bodies to handle the leads and people with an optimistic mindset to find customers.

As you start expanding to multiple offices and customer segments and you hire a sales manager or two – that’s when you need to start thinking about putting operations in place. When marketing and sales teams start to get bigger, that’s when they start to diverge. They sit at different places of the building and go through different processes of figuring out what they need to do. The role of both of our operations teams is to pull them tighter.

As a company matures, both of those organizations are going to mature, and without that operations glue that tells you what my team does and what yours does and make our work into one continuous supply chain, you’ll start to see things like marketing targeting the wrong customer segment and sales using sales motions that are not compatible with the leads coming in. That’s when bad things happen. You’re either spending money on pipeline that isn’t getting converted, or sales is converting pipeline that you otherwise would not want to convert. So operations needs to get more sophisticated. You need to start documenting things. You need to start aligning your processes. You need to start having more structure and governance in how you do everything. If you have these things and you’re staying on the same page with the same KPIs and constant communication, then you can typically grow your sales and marketing team together in the right sort of way as the company scales.

“We may give each other a hard time about our respective contributions to the supply chain, but we can help each other figure out: How are we going to get to the revenue outcome we want?”

Brian: It seems like you get that alignment and that sense of being one team for free when you’re small. And as the company gets bigger and more complicated, the role of operations is to preserve that oneness and single team mentality in how we work.

Jeff: One hundred percent. Let’s take hiring a dedicated events person as an example: we know how challenging it is to manage logistics of setting up and executing a great event, and that’s a core skill set that not a ton of people have. And you’re going to hire someone who’s optimizing that, but they might not be fully aware of the full process – how you gather leads, how you nurture them, and how you pass them over to sales. And that’s okay, because the role of that person is to put together really great events. That’s where the marketing ops team can work with the sales ops team to help pull that specific tactic you’re investing in into the overall process. The events person might not even ever think of sales other than who’s going to staff the booth to do what they do best.

Jeff: You and I believe sales and marketing need to be closely connected. What does a successful partnership look like?

Brian: I would echo something you mentioned a little while ago, which is that it’s really helpful when both parties think of the partnership as a supply chain. We’re all manufacturing the same thing on behalf of our employer, which is revenue for the business. The foundation of a successful partnership is understanding that.

“Once you understand the end outcome marketing and sales are driving at together, then you get to the fun part of the partnership”

It might sound routine or boring, but not everyone gets it. Some sales organizations are just in the business of acquiring logos rather than actually trying to make money for their business, because that’s the way their comp has been set up or what their leadership has set as a goal. Or more commonly, the marketing team might think, “Our job is building brand.” Being the revenue and operations person, my question is always, “To what end? We don’t sell our brand. We sell stuff, and the brand is supposed to help us sell that stuff.” Even if your job is actually to build a brand you always have to ask that follow-up question, “To what end?”

Once you understand the end outcome marketing and sales are driving at together, then you get to the fun part of the partnership, which is what you and I get to do together. Yeah, we may give each other a hard time about our respective contributions to the supply chain, but we can help each other figure out: How are we going to get to the revenue outcome we want? What’s the efficient way for our business to get to that goal? Are we staffed correctly? Do we have the right capacity? Can I actually drive the leads you need in the timeline that you need them?

That’s where the art comes into our roles. Because there’s not a playbook you can just execute. I wish there were. There’s rarely an obvious answer like, “Hire 10 reps, buy some Facebook ads, and the problem goes away.” That playbook has never worked for me. I don’t know anyone who it’s ever worked for. I don’t expect it ever will. So that’s why it’s key to get aligned in how we work, forecast and shape the future.

Because of that mentality, my experience working with sales generally has been good. At times when it has been very very bad, it’s because there’s a misalignment of expectations of what the supply chain’s trying to make and of the plan that we should have co-developed but often did not. Lastly, sometimes there can be a lack of understanding that both our jobs are hard. You can both know you’re supposed to be making money. You can both agree on a plan. But I’ll be a little folksy for a minute: my uncle has a saying that you should “never take out the trash when no one’s looking.” No one appreciates how hard everyone else’s job is if they don’t see it or feel it. You have to have empathy for the party on the other side.

Driving leads of quality is super hard. It’s super expensive, and it takes time. Closing those leads – of any quality, at any scale, on a timeline, and in a predictable way – is super hard. You start to see the fissures between departments when people forget that.

Tara Bryant on moving upmarket

Sales leaders need to be constantly looking out for their next million dollar opportunity. For many, that means considering whether it’s time to move upmarket. But the shift from serving smaller businesses to winning larger customers is a big one – and it represents a significant risk. Tara Bryant argues it’s not just about closing the deal. The best sales leaders work with their product counterparts to build a product that adeptly serves the needs of larger customers.

Courtney Chuang: One of the things I’m very curious about when you’ve reached the stage of growth you’re at is, how do you balance this pursuit of new customer acquisition with expansion revenue? I think a lot of companies struggle with investing in their current customers versus just trying to ramp up new local acquisition. How are you thinking about that?

Tara Bryant: That is always a big question that people have. I would say the number-one thing is: don’t have the same reps going after net new sales and expansion. It doesn’t work. The reason it doesn’t work is because it’s much easier to grow an existing customer than it is to go convince somebody to move, or to start using a new tool, right? Just subconsciously, people gravitate more towards the customer base and work on that, versus net new. So the number-one thing I would say is, don’t ever have them be the same person or the same team. And I actually think it’s a different DNA, in that I think people are either hunters or farmers.

I do think it’s really important, as you start to grow, that you have to look at your install base. You have to make sure you’re servicing them correctly, not only just to up-sell them — of course, we want more revenue — but really just to make sure: “Are they happy? Do they feel like they’re starting to outgrow us? What’s been so great about Pipedrive?” We started with a really small base of people who were SMB, really small customers. But they’ve been around for such a long time now that our customers are now 500, 600, 700 seats. It’s exciting, because we’ve been able to grow with them.

And so now we’re servicing these big — what I would call “metaprize” — customers now. Do we start focusing on that a little bit? Do we start looking at that? And if we weren’t servicing our base so well, we wouldn’t know that, right? So I do think it’s important to manage both of them but to look at them both very separately.

“You don’t want to go out there and sell to a big customer, when the worst thing you can do is not be able to service them”

Courtney: You touch on that really interesting idea of moving up market. I think it’s a temptation for a lot of startups, where suddenly they see a big company come in and they’re like, “Wow, that could be a really fast way to join this rocket ship.” But sometimes it’s a band-aid if they aren’t, as you said, really servicing their current customer base. When you’re thinking about moving up market, what are the crucial inputs you are thinking through before you say, “Yes, we’re going to go for enterprise?”

Tara: That’s a great question. We’re looking at saying, “First of all, do we have the right tool for them?” You never want to sell something that’s not the right tool for people. So I would say: “Could our tool support an enterprise customer? Yes, it could; that’s just not the segment that we’ve ever been really interested in.” And so as our customers have grown, and we’re seeing their needs, and we start customizing stuff for them, now we’ve got a package where we can start servicing the 800 or 900 employee customers. We still don’t have a team that’s actually just focused on that; they just come in pretty organically. But I think it is a market that we need to look at. I think you do have to start going up market a little bit.

Like you said, a lot of companies want to do it, and you do have to do it. But you want to make sure that you have the right tool first, right? You don’t want to go out there and sell to a big customer, when the worst thing you can do is not be able to service them, or it’s not the right tool. I think Pipedrive had to stay true to their values of how they started. It was for salespeople to sell more and to be able to be intuitive. That’s why we say it’s kind of cool to these small companies that started with maybe two or three seats five years ago, and they’ve got hundreds now. We like to think it’s because we help them sell more, right?

So it’s just making sure you stay true to the product and then making sure that you can really service the customers and that the product will benefit them, for sure.

These are only a sliver of what we’ve learned about sales as Intercom has grown rapidly over the past few years. Whether it’s establishing a close partnership between your sales and marketing teams or figuring out how to structure your company for growth, we hope you can find some value in the conversations we’ve had with these market leaders. They’ve certainly helped us get where we are today.

There are so many more lessons to be found in Intercom on Sales, the book we launched this week. Inside, you’ll find a collection of insights that ranges from hiring to creating an unforgettable customer experience to knowing how to navigate rapid change smoothly. Get your copy here.

Main illustration: Kylie Leuthold