The When, Why, What, And How Of Adding In Enterprise Sales

John Eitel, former VP of sales at Canva, describes himself as a sales problem-solver.

Having built sales orgs from the ground up PLG environments, he knows that there’s no relying on a tried-and-true playbook.

Success, John says, hinges on his ability to experiment and figure out what works in new and evolving contexts. That very challenge is what has made his career as a sales leader so rewarding.

Typical PLG companies start with a strong bottom-up or self-service motion—this is what drives the business’s initial success and growth. Meanwhile, sales is often associated with “old-school SaaS” and gets a bad rap in the industry. However, John says this is no longer the case.

“Sales is changing. The world of buying is changing. The way the consumers consume is changing. And so I think the successful sales leaders are the ones that understand how that evolution’s happening and how to embrace it and really lean into it,” he shared.

At some point, businesses are going to need a top-down motion to prevent a plateau. This is where sales comes in–and being able to embrace ambiguity when experimenting with sales.

John recently joined Blake Bartlett on the BUILD podcast, where he discussed how his problem-solver mindset has been critical to his career as a sales leader in PLG companies.

Say when: Signs it’s time to add in enterprise sales process

In this day and age, relying on old playbooks is old hat. Especially if you’re trying to map out what this process looks like. So what does the process of layering on sales in a PLG environment look like in practice? How do you know it’s time to make the change?

There’s generally three major signs that now’s the time for sales:

1. Customers pull you there.

John put it simply: “When you start landing bigger customers who exhibit different buying behaviors, it’s time to think about things differently.” This sign is clear and intuitive when you look at it in the context of a PLG company. Customer accounts want to grow bigger, and bigger than your self-service motion has the capacity to handle. So now you have to have a real sales conversation. You’re being pulled up-market to embrace the enterprise.

Maybe you’re a PLG company with its first big deal and you pulled out all the stops. If you’re hopefully expecting to close more deals of a similar size, it only makes sense to start building a process around it.

2. You’re running into stall points.

Say there’s a significant amount of untapped potential in an account. Your product should be getting more traction and use by the customer’s company. But you’re not making progress—and this is becoming a pattern across customers. At this point, you want to look for friction points in your existing buying process. Find out what’s causing these deals to stall out or grow to a certain size and stop.

Stall points in your deals have the capacity to evolve into stall points in your business’s growth. Addressing these areas often means adding in a human element.

In John’s experience, companies who have handled this effectively have “introduced a light-touch kind of sales motion.”

“It was someone who could come in and really educate, guide, and coach them through the sign-up process, and get them to the other side to get them adopting.”

3. Don’t make it complicated

In the early stages of transitioning into product-led sales, start small. According to John, you don’t want to overdo it.

“How do you come in a lightweight way to still kind of move through those stall points?” he asked. “Because I think the customers will value that and you’ll get a ton out of it because you can minimize a lot of your sales costs here.”

Legal agreements are a great example. In enterprise deals, it’s standard to expect that your client will want to review them. Instead of dropping the binder on someone, try to make it as simple as possible.

“Can we make it one page or less? Can we make it hugely customer empowering? Can we make it something that everybody in their right mind would sign up for easily and it gives us the right amount of protection?” John recommended.

The goal is for prospects to get through the terms without needing to go through a legal review. “That’s one example of how you hopefully can maximize these stall points and do it without a heavy human element there and just make it easier for buyers to buy,” he said.

Align on the why: Sales is essential for growth

Many PLG-purist founders are hesitant to embrace the top-down motion, as they believe that their past success is proof enough that they don’t need it. That instinct isn’t bad on its head. In fact, there’s a lot of benefit to stretching your business’s self-serve runway for as long as you can.

This isn’t a sustainable mindset for optimal growth, however.

“At certain points when you get a sizable enough engagement with an enterprise, the expectations of what they want you to provide is different,” John said. “They’re going to look for dedicated teams and dedicated points of contact. They want escalated support. They want different kinds of models of how they get treated.”

To close these deals, you’ll need to cater to enterprise expectations in addition to jumping all sorts of hoops in the name of legal, security, and support.

Some businesses are hesitant to make this leap because of how much success they’ve seen via self-service. In fact, they can end up overlooking following three considerations:

  1. As you land larger customers, sales becomes a necessary tool for maximizing customer success. Without it, you’re stuck doing lots of little deals for big enterprise companies, and you miss out on massive opportunities.
  2. Without sales, you run the risk of your product staying only as a tactical tool. Sales processes help your product break out of individual teams, and become widely adopted across an enterprise for a variety of use cases.
  3. If your business won’t cater to enterprise customers, someone else will. Other businesses with similar products in your category will notice that opening in the competitive landscape and take advantage of the opportunity.

What to do and how to do it: Communicating business value

From a 30,000-foot view, combining bottom-up and top-down, or product-led growth and sales means new considerations for your go-to-market (GTM) organization.

According to John, the key is using your entry points into an enterprise sales opportunity as proof of concept. If you already have a team successfully utilizing the product, they become your product champion. Your focus is to make them successful so you can leverage them as a business case to further encourage a larger deal with wider adoption.

“The really fun part about this is being able to take that now to a decision maker—in our context of Canva was the CMO—and being able to talk to them about this huge value-add that we could bring to their organization: how we could make them more efficient, how we could really help their team scale in effective ways,” said John.

Once you’ve made a connection with that decision-maker, you need to speak their language. In the case of business executives, this means:

  • drilling down the business value;
  • making a strong business case; and
  • proving ROI.

“A lot of these great PLG companies are creating categories. They’re creating solutions to problems that didn’t exist before,” John explained.

You’re not necessarily asking decision-makers to replace a tool they already are using with your product. You’re actually asking them to find a budget to pay for a tool that addresses a problem they may not have realized existed.

“You have to be good at telling the story of how the world with this product in place is going to be a better one for them: it’s going to save them money, it’s going to make them more effective—again, speaking in the languages of things that matter to them.”

This is where the ability to show usage and adoption becomes a superpower.

“Oftentimes the wall of resistance you hit is, ‘It’s going to be really hard for us to adopt a new tool, we’ve already got tool exhaustion. We just implemented X, Y, Z,’” John explained, “And so to be able to say that it’s already happening with some virality—teams have already selected this tool and they’re getting so much value out of it already—you can go talk to them firsthand. I think that really helped us speed the path up and really in the end also shorten the sales cycles.”

Though your internal teams clearly see the business value of your product, your users look at it from a different lens. They probably aren’t thinking about it in terms of ROI, but likely through the lens of personal preference. “The common words they use are, ‘It makes my life easier, helps me do my job more effectively, or it makes me stand out from my peers,’” John said.

Take that preference and find a way to translate it to dollars and cents. It starts with finding a way to get these champions to quantify their saved time and efficiency. That’s what will ultimately build into that ROI.

Tackling the transition as a team

No matter where, when, or how you start building your sales org, it’s important to remember that the majority of your company is not on the sales team. However, this transition can and will result in some significant cultural changes for most PLG startups.

Adding in this top-down motion to embrace the enterprise may be accomplished by adding a sales motion, but it’s not a sales-only problem. This is a team sport, and navigating this change successfully is the whole company’s responsibility. Everyone needs to be on board.

That puts the onus on leadership—sales leadership especially—to provide valuable context regarding this change and how it’s critical to grow to the next level.

When John joined Canva, he was the first sales hire in a company of over a thousand employees. A lot of his responsibility was educating the rest of the company about what sales means and looks like in the context of a PLG model.

“I would say part of my role was being like a chief storyteller,” he said, working with product, marketing, and support, and “really diving into the trenches and helping them kind of understand the value that we can drive together.”

Mikaela Gluck
Mikaela Gluck
Contributing Writer

Mikaela is contributing writer at OpenView. She specializes in writing articles for VC and product-led SaaS startups, and is dedicated to creating content that is both educational and unique.
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