The First Steps of Product-Led Sales: Finding the Right Leader, Building Out Teams, and Fostering Sales Culture From Scratch

May 19, 2022

When we first started talking about product-led growth (PLG) at OpenView, a lot of rhetoric centered around how companies don’t need a sales team to see growth. As the PLG world matured and evolved, however, many companies wished they started with sales earlier.

Today, PLG companies recognize the value of sales teams for winning enterprise deals and adding another go-to-market track. The question has shifted from “Do we need sales at all?” to “When should we layer sales in?”

I sat down with John Eitel, who was most recently global Vice President of Sales and Success at Canva and Kyle Parrish, VP of Sales at Figma, to address this very question, and to learn from their experience as first sales leaders at their prospective companies.

When to start thinking about sales

Long story short, “It always depends on the situation,” said John. “The key is looking at your specific scenario and trying to think about how you can extend the runway of product-led as long as possible.”

“For product-led growth, you’ve got to nail that motion and get some momentum,” Kyle said. “It’s hard to come in and build a successful sales team and go to market wing on top of product-led growth if it fundamentally isn’t working.”

Both Kyle and John agreed that reaching a perfected self-service, product-led motion is the first sign that your business may be ready to layer in sales. Here’s another sign. “When you start to see different points of friction emerge—that’s when you start to think about how we leverage human involvement here,” John explains.

Bigger deals, more growing pains

It’s likely that the friction will be a direct result of your business trying to accommodate bigger, more complex deals.

“With Canva specifically, we started to see that when deals got over a certain size, people wanted to talk to a real human,” John said. “They wanted a higher level of engagement from an onboarding perspective. They started to bring in procurement and attorneys and other pieces, so contracts got more complicated. So [sales] was really a natural evolution for us to think about. It was time for us to apply human talents on top of a really great product-led growth engine.”

Lessons for first sales leaders joining PLG companies

When introducing sales to the business, Kyle emphasized that building a sales culture is just as important as building a sales team. Many people may have preconceived notions about sales culture in the SaaS world. Unsurprisingly, it can be a legitimate concern that stereotypes of salespeople will put off internal teams. They might have fears that a sales org will make the culture evolve in a way they aren’t on board with.

It’s up to your business’s first sales leader to chase away those fears and create a new culture that fits within the existing one in a PLG company, according to Kyle. Having the right person lead the charge can ultimately help build the right type of sales culture internally.

“You have to bring in the right leader who knows how to build a culture from nothing, and fit within a small PLG company culture,” said Kyle.

John echoed this sentiment. “You need to find the right leader to come in here,” he recommended to PLG founders. “Someone who is really collaborative, cross-functional, and who can really come in and be a bridge builder.”

Kyle and John shared some advice for first sales leaders attempting to build a strong sales culture, both internally and externally:

  • Challenge misconceptions internally. John shares his experience of starting the sales team at Canva. “There was just this preconceived notion of, do we need a sales team? Why are we doing this now? And so there was a little bit of myth busting and a lot of over-communication that I had to do in the early days.”
  • Keep customer experience at the forefront. A lot of companies can hit ARR (Annual Recurring Revenue) milestones, but if they’re throwing customer goodwill aside in the process, it’s going to catch up to them. “For us, it’s not just, are we increasing revenue, expansion, customers,” said Kyle of his team at Figma. “It’s ‘Are we also making sure that we’re positive in terms of the evolution of the culture and how our community perceives working with the team?’”
  • Prioritize your business’s core values—and live them. “We have a number of things that we look at and celebrate as a sales team, but one of them is being a cultural legend,” John shared. “It’s a pure nominated thing that everybody in the company can vote on to nominate you for. And it’s about sellers that live the core values. And just that subtle statement alone gets salespeople to think about not only winning, but also winning in the right ways.”
  • Stay in lockstep with marketing and product. Accomplishing this synergy has been central to John’s success at Canva. “We’ve formed a triumvirate of sales, product, and marketing, and we meet regularly and we are always in lockstep and talking about the different experiments we’re doing—and making sure we tie it back to that customer journey so that you don’t have one team launching off and doing something that completely flies in the face of what the other team’s doing,” he shared. “If you’re doing it right, they all should work together and drive towards common goals.”

How to build out a sales team

There’s no one right answer for which hires to make and when to add them. According to Kyle, bringing in people at different levels should be based on business momentum and the appetite to build out the sales arm.

Asking your sales leadership to hire the right person with the best traits and skill sets can be self-limiting. But when it comes to building a team that can thrive in a product-led environment, Kyle and John shared some valuable insight into the people that make a good sales team great.

Find problem solvers who can handle change

“I’m always thinking about not someone who could do the job, but someone who’s going to bring the same level of excitement and energy and optimism that I do to the job,” said Kyle. But this focus on personality goes beyond sheer enthusiasm.

Kyle and John both stressed the importance of hiring people who are comfortable with ambiguity and enjoy problem-solving. In early stage companies where priorities can shift on a dime, being able to handle a high pace of change and experimentation is crucial.

The challenge of having to chart your own path can be stressful. It’s all about prioritization, aligning with the CEO and leadership team to establish the right moves.

Ultimately, it’s these actions that can turn out to be the biggest needle movers and get you to that next stage of growth. It’s definitely not the right environment for just anyone. But for some people, this is what’s most appealing about the opportunity. These are the salespeople who are going to help your team succeed.

Recruit a diverse set of domain experiences

John recognized the value of recruiting a team with a diverse range of domain experience as he built out sales at Canva. They hired some sales leaders from Dropbox who had experience going from a consumer to enterprise motion, said John. However, he was cautious not to hire a full team with the same background to ensure they were getting a variety of perspectives and angles on any given problem.

According to John, diversity in domain experience, “really lends to helping you solve these things quicker without making the same mistakes over and over again—because you get the learning curve,” he shared.

“But you also get to compare notes on what worked and what didn’t from others, and you can combine and use that in a cumulative effect.”

Build a balanced sales org structure

Your first sales leader is going to be responsible for creating the structure of the sales org, and will have to make decisions about segmentation of teams before hiring those first managers.

Kyle emphasized how having a clear idea of what focus areas you want each team to be held responsible for will help you recruit managers with the right experience. For example, if you’re looking to carve out a dedicated enterprise sales team, you’ll want to look for a leader with enterprise sales experience who may have also done some early stage building.

Hit the right ratio of manager to rep

You also want to hit the right manager-rep ratio—there’s a delicate balance between not being too top heavy with management, but also not having too many direct reports under one manager. There’s no magic number that works for every company across the board. In fact, the ideal manager-rep ratio can vary within a single sales org depending on the segment.

Take enterprise sales teams as an example.

“You just get more complex customers, more complex deals, and even a smaller amount of reps would be a full workload for a manager,” Kyle explained.

Whether you’ve got eight or ten reports per manager, what’s most important for the success of your teams is that you ensure reps have access to the support they need.

Reinforcing the value of sales across the business

You might find that some people in your company believe that sales is inherently incompatible with their product-led DNA—people who believe that product-led or sales-led is a one-or-the-other proposition.

But, as John assured us, it’s possible to win these people over and help them understand how sales can benefit them. It just might take time and a lot of repetition.

“I find myself having to beat the drum of what the importance is and how to make it work effectively,” John said. “And I think you have to deputize other folks on your team to also be active in that mission. I have all of my leaders doing ‘Ask Me Anything’ sessions about sales at Canva and brown bag sessions—I think you just have to be able to really tell the story internally to get others to buy in and believe in this. It’s showing up in company meetings to talk about joint wins of how product-led plus sales-led leads to this really great outcome.”

Partner at OpenView

Casey leads the end-to-end strategy & programming for OpenView’s network of industry experts, advisors & corporate partners. Her role is focused on creating connections between founders & their teams and the partners, advisors, board members & events they need to reach their goals. Additionally, she manages the OpenView portfolio peer networks and hosts the #WeeklyWalk series.