Product-Led Sales (PLS) AMA: Chris De Vylder

Alexa, CEO of Pocus, hosts Product-Led Sales (PLS) “Ask Me Anything” sessions with PLS experts to share best practices, frameworks, and insights on this emerging category. These AMAs are an opportunity to ask PLS leaders any question — ranging from hiring to sales compensation to tech stack — in a low-key, casual environment.

The PLS AMAs are for members of the Product-Led Sales community, the go-to-place to learn, discuss, and connect with go-to-market (GTM) leaders at product-led companies. The goal of the community is to bring together the most thoughtful and innovative GTM leaders to build the next generation of sales together.

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Meet Chris, Chief Revenue Officer at Sentry 👋

Chris De Vylder has spent his entire working life in the tech world.

His career originally kicked off in the semiconductor industry, but today his expertise lies in sales strategy and operations. In his former roles as Global Head of Sales Strategy & Ops then as Global Head of SMB Sales at Atlassian, Chris led the charge to create a hybrid sales approach that combined traditional, enterprise sales practices with a product-led growth (PLG) motion. His efforts helped grow the sales team from less than 10 to 400 people, and scale revenue from $400 million to over $2 billion. 

In mid-2021, Chris became Chief Revenue Officer at Sentry, where he leads the go-to-market teams as the organization continues to expand its PLG motion — a path similar to the one he took at Atlassian years before.

Continue reading the AMA recap to learn more about:

• How Atlassian became a strong leader in the PLG space 
• Tips from Atlassian and Sentry on avoiding cannibalization
• When and how to grow your PLG sales team 
• How to tell if the PLG motion is right for your business

What Practices Helped Make Atlassian a PLG Standout?  

Of all the companies Chris has seen and worked at, he says that Sentry is one of the most similar to Atlassian when it comes to its foundational elements:

• Thriving product-led motion
• Robust user community 
• Small sales team (ten quota-carrying folks at Sentry when he started)

That’s why the path he’s taking to build out the sales org at Sentry looks quite similar to his experience at Atlassian.

What are the key elements that Chris thinks helped make Atlassian, founded in 2002, a leader in the PLG space — one that’s worth following in the footsteps of? 

Patience: Patience is indeed a virtue when it comes to PLG companies. The best way to make space for patience? Reduce external pressure. Atlassian was able to do this by remaining bootstrapped, and therefore exempt from the pressure of investors who want growth at all costs, for almost a decade. 

Dedication to the PLG Flywheel: Because they could be patient, Atlassian’s team took their time building a robust PLG flywheel — which Chris says is still a huge source of new customers. 

Pricing Transparency: From the get-go, Atlassian has been up front about their pricing — even for enterprise customers. Still now, you can buy any of their products directly through their website, no need to contact sales if you already know exactly what you want. 

Sticking to Their Guns (Even When Unpopular): Unwavering pricing transparency, the lack of negotiating on that pricing with customers of any size, the focus on bootstrapping and slow growth — if some of these business decisions seem a little unconventional it’s because they are, and were even back when Atlassian made them. But thanks to the time and flexibility allowed by bootstrapping, Atlassian’s leaders could make and stick to unorthodox decisions. 

It bears noting that the competitive landscape, current best practices, and other factors can make the elements of Atlassian’s PLG success difficult to replicate today. However, they can still serve as guideposts for younger PLG companies, or established ones that are looking to layer this modern motion into their business.

“What bootstrapping afforded Atlassian to do was say ‘We are going to grow this company at the pace that we want to grow it at.’ They were able to set a pace that didn’t  jeopardize their long-term foundation. That can be hard to replicate.”

How Patient Should You Be? ⏳

According to Chris, the mantra at Atlassian was always that patience was the core to Atlassian's strength. Everything they do is tied into that.

So should you be patient like Atlassian? And lean into your PLG flywheel. Or should you focus on hitting aggressive growth targets by accelerating time to value? 

Chris says the level of patience you can afford to have is all about the landscape.

The bottom line is that some markets are especially competitive. If you're ever going to capture your unique spot in what Chris calls “monopoly markets,” you simply must move quickly and make investments in marketing and sales to accelerate customer acquisition.Once you own your space in the market, you may be able to slow your pace. 

But if that isn’t the kind of market you’re in, Chris advises to take your time a little bit more.

Chris: “It's going to depend on the market that you're in and the competitive landscape. If you can afford it, go the slow route — you're going to own much more of your company at the end of the day.” 

Avoiding PLG Cannibalization in a Hybrid Sales Environment

Chris has a lot of experience getting sales to work like an extension of PLG, instead of setting up the two approaches like adversaries that must battle over leads. 

For him, at both Atlassian and Sentry, it’s been all about finding strategies to layer sales into the flow where it makes sense. In this way sales supports, not cannibalizes, what’s working with the PLG motion. 

Chris: “Both here at Sentry and at Atlassian, we try to not build in anything that would cannibalize the strength of the PLG motion.”

Atlassian Takes Hands-Off Approach 

Though it has been tweaked and tested over the years, Chris gave us the blueprint of the “smart touch” approach Atlassian took during his tenure to avoid cannibalization of either their sales program or PLG motion. 

Acquisition by Flywheel: At Atlassian the core customer land motion is always led by the flywheel, no outbounding or forced interactions with sales. 

Sales Drives Expansion: The main role of sales, then, is to identify opportunities in the PLG funnel to upsell and cross sell across product lines.  

No Proactive Engagement: The Atlassian team lets new users enter the PLG funnel and find their way around the product at their own pace. No help is offered unless requested. 

Customer and Product Specialists on Standby: When a customer raises their hand for help, Atllassian has a team of customer and product advocates made up of licensing specialists, pricing specialists, and product solution engineers who are ready to assist. 

Sentry Goes More Outbound

Chris tells us Sentry’s sales team is a little more hands-on with their sales and PLG motions. This is in line with their ambitious growth goals — and the fact that their flywheel just simply doesn’t produce quite the number of sign ups required to achieve growth targets akin to Atlassian’s flywheel.

Outbounding to ICPs: At Sentry, sales takes an outbound approach to engage with people who align with their ideal customer profile (ICP), but aren’t currently using their product.

Build ‘islands’: Proactively offering customer success assistance to build initial ‘islands of Sentry’ within an organization. Sales then can leverage these raving fans to expand the account. 

“The strength of PLG companies is that they’ve figured out a go-to-market motion, a market, and the user experience they need to build so people can adopt the product by themselves. Then, they can add some acceleration, or quite a bit of acceleration, into that through sales. As long as they approach it carefully and avoid cannibalization.” 

Atlassian’s Playbook-Focused Sales Expansion Strategy 🌱

As Chris tells it, in the beginning, Atlassian was a product that only existed behind the firewall at most companies. The only motion was customers downloading and installing the product themselves.  

After realizing enterprise customers specifically needed some special features, they created a more robust version of the products they were already offering (today this is called Atlassian Data Center), and thus a new playbook was born.

At the time, pretty much the entire sales playbook was focused on upselling high-volume customers on Atlassian Data Center. Next, another playbook was developed that focused on migrating existing customers to new cloud offerings. Then, as Atlassian started to expand the product portfolio, both organically and through acquisition, the sales team expanded and a flurry of new playbooks also hit the scene.

Around each new playbook, they built what Chris calls a “wallet model.” This construct helped them determine what a customer would be worth if converted at scale to a new product. Atlassian sometimes even built dedicated sales teams to execute on specific playbooks. Chris says the approach was relatively straightforward. Accounts were prioritized for specific playbooks and existing relationships were leveraged to upsell or cross-sell products.

Hiring for Sales in the PLG and PLS Space

We agree with Chris that sales looks so much different today than it did 20 years ago, around the time Atlassian was founded. 

He walked us through his main tips for making good sales hires today in PLG and PLS-led companies: 

• PLG Alignment: Make sure a new hire understands and is comfortable with the PLG motion and hybrid sales environment. You don’t want a traditional salesperson who is only going to gun for deals that cannibalize your existing model. 

• Prioritize Experience When You Can: These days, you can actually find sales people with PLG experience. There’s Twilio, GitLab,New Relic etc. Specific PLG experience shouldn’t be a dealbreaker, but why not give yourself a head start when there’s already a pool of qualified candidates out there?

$5M: The Hiring Trigger

When should you start bringing in those PLG sales hires?

Chris has a pretty easy rule of thumb to go by: you know you have a solid PLG flywheel when you can reach $5M in ARR without a traditional sales motion.

Hitting this threshold means your PLG motion is solid, that people are actually using your product, and that generally they’re pretty happy with it. Even at just $1 or $2 million, if you can afford it, Chris recommends hiring just one sales person to start experimenting with what a bigger sales org may look like. This prepares you for when it’s really time to hit the gas. 

It is especially beneficial to layer in sales when you hit this level for several reasons:

• You’re going to start serving enterprise customers who want and need white-glove assistance at times 
• If you don’t at least try to capitalize on these enterprise accounts that are ripe for the upsell, you’ll likely be leaving cash on the table
• Sales folks are uniquely skilled in shaping your product value into a narrative that connects with senior-level buyers, something that’s vastly more important now that you're asking for a $500,000 check versus a $5,000 one 

Rule of thumb: starting hiring sales @ $5M ARR

Leveraging Data to Prioritize Sales Outreach: Keep it Simple 

Chris says it wasn’t until close to the end of his run at Atlassian that he saw the company 

develop sophisticated models that helped prioritize sales outreach based on a customer’s propensity to buy. He adds that a simple initial approach is often more effective, based on easily understandable heuristics that are intuitive for the sales team. 

For most of his time at Atlassian, the process of using data to identify sales opportunities was pretty manual. Sales would see an email land, use that information to determine industry and company, then ask “What could this lead be worth to us?” For leads with a lot of upside, upsell and expansion playbooks were most commonly exercised. 

In Chris’ dream world, he says he’d love a product that captures the white space of an entire company the moment one of their employees lands in the product for the first time. 

Is the PLG Motion Right for Everyone? 🤔

No, taking a PLG approach isn’t going to work for every single business on the planet. However, Chris thinks it can work really well for a lot of them. 

These are the top factors that Chris sees in successful PLG companies, no matter the product or audience type: 

Use Cases That Serve the Department Level: Self-serve is the underpinning element of an effective PLG motion. At the department level (like marketing, for example), there will almost always be a use case for a product where customers can onboard themselves. This is foundational to the land-and-expand motion that works so well for many PLG businesses. 

Usability: Again, it all goes back to self-serve. If it’s difficult for a new user to get started on your product, you’re not going to get the engagement you need to expand or upsell them later on. If you can’t make your product intuitive enough for self-serve, it’s probably not a good fit for a PLG approach. 

Virality: A product that can be used across the company — think collaborative tools like Figma, Notion, etc. — is just going to have an easier time spreading through departments with less effort from sales. 

We’ll See You at the Next PLS AMA 🔮

We had an amazing time learning from Chris — and there’s more where that came from. 

To get your own questions answered in an AMA by today’s top PLG and PLS experts, all you have to do is request to join Pocus’ PLS community.

In the community, you’ll be able to engage with plenty of experts and of course attend every AMA in real-time to ask all your burning questions.