Building Sales Teams From The Ground Up In PLG Environments

I’ve spent over two decades in sales, starting in the nascent enterprise SaaS world at an early-stage startup going through hypergrowth. I knew sales was for me when I found myself having fun being part of the chaos that ensued.

The last two companies I worked at—WP Engine and Canva—were heavily product-led growth (PLG) focused. The businesses started with this PLG motion but soon saw they were gaining traction on the enterprise route.

In fact, they combined an enterprise sales process with product-led sales—proving to be a real art form. Soon, it was up to me to build out sales teams equipped to handle this dynamic from the ground up.

One of the challenges I faced was creating a solid sales team to support an enterprise sales layer. When adding so many team members while growing at warp speed, it really puts a lot of pressure on you to make sure that you have a solid hiring system in place. Hiring mistakes are inevitable, but you need to be getting it right more than you’re getting it wrong.

Sequencing sales hires

A question I get asked a lot by founders is who to hire first. Unfortunately, there’s no ironclad answer that applies across the board. When deciding how to prioritize and sequence hiring for your sales org, there are several factors to consider. These include:

• your product
• the market you’re targeting
• and the current economic landscape.

When I’m talking to a founder about developing a hiring strategy, I’m looking to understand how they’re selling today. What are their channels for acquisition, and how are they being met? Furthermore, I want to know where the breaks and stall points are. Where are they seeing challenges with winning, onboarding, or keeping customers?

These questions help you get a pulse on an organization. Sequencing hires starts with being able to:

• Assess the situation;
• Identify the variables and breakdown points;
• Diagnose areas that need attention; and
• Prescribe a hiring solution.

For example, maybe a company is able to win customers just fine, but they get locked in at a small size. If you want to have a bigger footprint in an organization and get more users on the product, consider adding customer success and onboarding components.

Keep your sights set on the ultimate goal, which is to build your team just in time (not too early, not too late), while keeping sales costs in line.

For me, that’s the fun part. I get to dig into where the challenges are, identify what needs should be met first, and then map that back to which hires take priority over others.

Diversity is the heart of high performing sales orgs

Even before diversity, equity, and inclusion were used as crucial hiring metrics, I saw the value in bringing unique personalities and diverse backgrounds together to solve a problem.

I’ve seen it proven time and time again throughout my career:
Diverse teams will outperform non-diverse teams any given day, even on a Sunday.

My advice to new sales leaders is the following:

1. Resist the urge to gravitate towards what feels easy and comfortable, and
2. Push yourself outside your comfort zone.

This really matters when it comes to hiring.

I also try to help them spot their own unconscious bias. In a hiring follow-up panel, I might ask young leaders why they liked a certain candidate and what made them a good fit for the role. I’ve heard people mention that a candidate seemed like a cool person they’d want to have a beer with many times. In these cases, I made it a point to explain how unconscious bias could be at play here, and why that wasn’t a good reason to bring someone onto the team.

Hiring diversely needs to be at the front of everyone’s mind from day one because it’s so important to get right from the beginning. A lack of diversity can be a flywheel that supports itself, and is hard to turn around once you’ve gone the wrong way.

When candidates join a Zoom call where nobody looks like them, it’s very likely that they get the sense that they don’t have a place at your company.

Prioritizing a data function

When I think about product-led growth teams with a sales-led component on top, a focus on data tends to emerge as the biggest area of opportunity. Insights on users—in particular, their behaviors and buying patterns—are a superpower for a sales org when leveraged correctly.

This data helps to:

• Sequence hires by giving you a sense of what volume of leads you can expect to be managing, and
• Ultimately determine what kind of team needs to be there to handle it.

On an individual performance level, data also enables individual contributors to do their best work. Typically, it can take anywhere from three to six months to ramp somebody up, but if you give them data and insights, you can significantly shorten that window.

Using data helps you see new opportunities for everyone

In my own career, there have been times where I prioritized getting a resource allocated internally from another department or hiring within my sales operations org to get someone to focus on the data.

In one such situation, I sat down with a high-performing member of my sales team. I wanted to understand what made him so effective. When I looked at his activity metrics, they were much lower than everyone else on the team, yet he was having the highest success.

When I learned how he was leveraging his background and education in software development and data, I started thinking about ways I could model what he was doing. With this information in mind, I elevated him into a role that allowed him to assist other people on the team.

Encouraging sales experimentation

Shortly after I joined Canva, we reached the height of the pandemic. I sat down with my account executive (AE) team to go through the pipeline and discuss the deals we’d be working on that quarter. Their biggest concern was how to sell a tool at a time when companies were laying off thousands of people a month. We didn’t want to come off as tone deaf.

I took all that feedback and went to the founder, knowing that we had to find a solution that was in line with our brand. It also had to show heart and compassion during a challenging time. We decided to give our AEs a quota for free trials. We wanted them to give away free six-month trial periods of the software—no commitment or strings attached.

The next step after this six-month period was to figure out how to convert all these new users to paid customers. We ended up seeing a really high success rate.

You might attribute this success to simply a good idea at the right time. However, I see it as the product of an open culture of experimentation–a core value we fostered at Canva.

It’s really important for companies, early-stage companies especially, to get comfortable with trialing things and building that into their culture and the DNA of their teams. Make sure it’s always okay to try new things and learn from them—win, lose, or draw.

Where to start running sales experiments

When it comes to building out successful sales processes, experimentation can take your org to the next level. There’s definitely a point where you can get to a great operational scale and reduce the amount of experimentation. But in the early stages, don’t be afraid to try two to four different things. Try making changes in the following areas:

Compensation and teaming models

Several years ago, I experimented with a team-based comp model. We tried it out in tandem with our generic comp model, and it turns out that it yielded better results. When you tie experiments to compensation, you also ensure that your team is on board and motivated to improve.

Hiring profiles

In fast-growing companies, what you often find is that your needs six to nine months ago aren’t what you need for the next leg of the journey. When making those next hiring decisions, ask yourself: What’s changed in the business since the last round of hiring? Try to find someone with a slightly different profile and see how that works.

Structuring sales engagement

With PLG, users who sign up on their own are your entry point into an organization. At Canva, when a large number of people from the same organization signed up, we reached out to their chief marketing officer (CMO) and led by telling them how many people in their company are already using the product.

This approach, we learned, often got a negative reaction out of CMOs and made them feel out of control. So we decided to change the flow and move the adoption stat to a different part of the sales process.

What to avoid while experimenting

On the flipside, sales experimentation is not a foolproof process. Although you can never truly predict an experiment’s outcome, there are ways to ensure that you:

• Have too many experiments going at once. With so many variables in the mix, it can become hard to attribute success or failure to one given experiment. While it’s important to try a bunch of things out, make sure your experiments won’t lead to inconclusive results due to overlap.
• Are not giving your experiments enough time. You need to have enough horizon in your experimentation to really see the results, good or bad. If you pull the plug two weeks in, you can miss out on positive outcomes and successful behavior changes. Avoid this by giving these experiments another month or so, for example.
• Are not aligning compensation to your experiment. It’s only human nature for people to act in a way that’s best for their situation. When I’ve put people into experimental teams in the past, I guaranteed their comp so they wouldn’t be tied to the outcome, regardless if they succeed or not. This opens people up to embrace change and give the experiment their best shot.

Four key takeaways for building sales orgs with PLG

• Sequence hires based on your business’s challenges. Once you’ve identified the weak points in your current process, determine where the greatest need is and map that back to which hiring profiles will best target said need.
• Think about diversity before you start building out teams. The value of bringing together a variety of different backgrounds and personalities can’t be understated. Start thinking about diversity early, because diverse teams attract diverse talent.
• Consider adding a data function. For PLG businesses in particular, task someone on your team to source actionable insights. These insights when acted upon by other individual contributors can skyrocket your org’s performance.
• Experiment as much as possible, early and often. Try changing up team or comp models, hiring profiles, or how you structure sales engagement. Win or lose, you’ll learn valuable information to iterate on going forward.