1. Wait for the pull, not just opportunity
Most founders and revenue leaders make a fundamental mistake when considering an SLG motion: they add it based on perceived market opportunity rather than actual customer behavior.
"The question I get a lot is, 'I want to add this sales-led component because we think there's going to be interest in this new market,'" John explained. "That's a tough one if you haven't gotten those signals, proof points, or early adopters. You've got to get the early adoption first."
The key psychological principle at work here is confirmation bias. Leaders who want to add sales often see what they want to see in the market, prematurely interpreting general interest as validation for a full sales motion.
Instead, look for these specific signals:
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Larger companies already using your product through self-serve channels
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Multiple users from the same organization signing up independently
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Users running into limitations with your self-serve offering
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Companies reaching out directly for enterprise features
At WP Engine, John spotted this pattern when companies like Patagonia started using their platform through self-service channels. When interviewing these users, he discovered they were marketers who had used WordPress in their personal lives or at small businesses and were now bringing it to larger companies. But these users were hitting limitations and couldn't get the support they needed.
Similarly at Canva, John observed that they had nearly 200 customers at major brands where teams of 10-20 people had independently started using the platform at work after being denied resources by internal design teams. These users weren't using Canva collaboratively and often didn't know others at their company were using it too.
Only when you see these clear behavioral signals should you begin validating an SLG motion. It's about responding to pull from the market, not pushing a new strategy because it seems like the next logical step.
2. A five-step playbook for SLG transformation
Once you've confirmed the pull exists, resist the urge to immediately start hiring account executives and scaling a sales team. According to John, successful transformation follows a five-step journey that most companies rush through or skip entirely.
I thought his approach was extremely thoughtful and pragmatic because I've seen companies try to compress these phases or skip ahead to commercialization too quickly, only to find themselves with a sales team but no clear offering.
The five-step PLG to SLG journey:
Step 1: Validation
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Interview users who are already using your product at bigger companies
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Partner cross-functionally (John worked directly with the CPO at WP Engine)
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Verify genuine market pull rather than trying to manufacture demand
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Get deep customer insights about their usage patterns and challenges
John emphasized that you can't force this transition if the signs aren't there: "You've got to get the early adoption first or those signals." At WP Engine, they interviewed about 25-30 enterprise customers who had organically signed up through PLG channels to deeply understand their needs and requirements.
Step 2: Solution & product offering build
Transform early learnings into product requirements:
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Identify not just current pain points but future challenges customers will face
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Work closely with product teams to define the enterprise offering
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Use this as an opportunity for sales leaders to learn business beyond sales
At WP Engine, the enterprise offering addressed specific needs that individual bloggers never required:
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Security and compliance features including DDoS prevention
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Single sign-on capabilities and enterprise authentication
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Stability and scalability through siloed environments for large customers
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White-glove customer success and support with dedicated teams
John explained: "When you're building for content creators who aren't doing it at the scale of an enterprise brand, you don't think about traffic spikes. There's always this talk of, 'What if you got featured on Shark Tank or the Super Bowl?' Are you ready to scale up with increased demands?"
Step 3: Commercialization
Develop pricing and packaging through a lightweight but thoughtful internal process
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Create enterprise-grade terms and SLAs while keeping them simple
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Balance bottom-up cost analysis with competitive market positioning
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Set prices with room to grow; avoid starting too low
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Consider handling pricing internally versus hiring consultants
On pricing strategy, John noted: "It needs to be anchored in the bottoms up there. If it doesn't make dollars, it doesn't make sense. But it needs to be a bit of a stretch, aspirational. You don't want to start too low because it's going to be a slog to move the marker up over time. Once you set an expectation, it's hard to change."
Step 4: Playbook Design
Develop positioning and messaging documents
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Create basic prospecting strategies and sales decks
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Accept that it won't be world-class in year one
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Focus on the fastest path to getting up and running
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Iterate and build more repeatability and sophistication in year two
John acknowledged that the initial sales playbook doesn't need to be perfect: "In year one, it probably wasn't world-class. It was the fastest path to get us up and running. Year two is when we really started to think about scaling this with some repeatability."
Step 5: Team Build & Infrastructure
Build the sales team concurrently with playbook development
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Plan for rapid scaling (WP Engine doubled their team every year)
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Adjust hiring profiles as you move upmarket
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Invest in world-class onboarding and enablement systems
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Develop the technical infrastructure to support enterprise sales cycles and larger sales teams
At WP Engine, John recognized that the profile of reps they needed evolved as they moved upmarket: "We started to see success with the early segments of our focus. And so then we were like, 'Let's move even further upmarket.' That means probably folks that have done this at that level mixed with folks that are really showing the willingness to learn."
The key is patience and proper sequencing. Don't rush to scale until you've thoroughly completed each phase. Most companies compress the timeline, leading to mismatch between what sales is selling and what the product can deliver.
3. Build distinct products for distinct needs
A common debate is whether to create a separate enterprise product or simply sell the same product at different tiers. John has seen both approaches work, but found that splitting the product lines creates clearer differentiation and reduces cannibalization.
This approach aligns with the psychology of value perception. When you build a distinct enterprise offering that addresses specific enterprise challenges (rather than just bundling more features), you create a clearer value proposition that justifies higher price points. Enterprise buyers are not just looking for "more" of what individuals use; they're looking for fundamentally different capabilities.
At Canva, this meant:
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Building brand controls for CMOs concerned about consistency
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Creating team collaboration features
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Enabling organizational structures within the tool
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Adding enterprise-grade security and compliance
As John explained: "Sales has its own organization built into the tool, marketing has its own. It's not just that if you've ever used Canva, you can see all the designs that you've created. If you're an organization, you don't want to see everybody's designs all at once. You want to see the ones that matter to you."
For WP Engine, this meant building separate, siloed environments for enterprise customers with capabilities like on-demand resource scaling for traffic spikes, fault tolerance and geographic distribution, advanced security including DDoS prevention and detailed logging for security teams. That’s quite a different solution.
The most successful approach is to think about your enterprise product not as your self-serve product with more seats, but as a solution built for fundamentally different use cases and stakeholders.
4. Hire the right profiles for early SLG teams
Building your first SLG team requires careful consideration of who to hire. The profile for these early hires is significantly different from what you'd look for at a mature sales organization. John recommends prioritizing "stage fit" over traditional enterprise selling experience.
This connects to what psychologists call "person-environment fit theory," the degree of compatibility between an individual and their work environment. Early-stage SLG requires a specific mindset that many experienced enterprise sellers lack.
For both WP Engine and Canva, John looked for salespeople who were:
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Adaptable and comfortable with ambiguity
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Naturally curious and excited about solving new problems
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Resilient and able to handle constant change
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Willing to help shape the product offering
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Comfortable giving product feedback
He specifically warns against hiring from established enterprise companies: "It's critical to understand the stage fit... a common mistake is thinking 'we're going to compete with Adobe, so let's grab some reps from Adobe.' The Adobe rep freaks out in the first week because there's no onboarding, no training, no manual."
In terms of sequencing hires, John suggests:
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Start with individual AEs (2-6)
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Add a sales leader once you have critical mass (around 6-8 reps)
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Add Customer Success Managers at nearly 1:1 ratio with AEs initially
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Add enablement when you reach 15-20 team members
The key is to start with sellers who can act as partners in building out the motion, not just executing a pre-defined process. As John describes it: "In most of those cases, it allows you to really see what's possible and if there is some 'there' there, and then you can double down on those experiments or pull back."
5. Create clear boundaries to prevent cannibalization
One of the most critical decisions is determining how your PLG and SLG motions will coexist without cannibalizing each other. John advocates for establishing a clear "firewall" between the businesses with distinct leadership and clear rules about which customers belong in each segment. Establishing clear rules prevents internal conflict and market confusion.
At WP Engine, John implemented a simple company-size boundary:
This division had exceptions. When large companies like Patagonia self-signed up, they were "rerouted" to the enterprise team to ensure they had the right solution. But the firewall remained clear.
Canva used a similar approach, setting a firm boundary at 300 employees:
John emphasized that this isn't just about preventing cannibalization; it's about cost efficiency: "Your sales costs really spiral if you put a sales rep on everything. That's a failure some people make. They say, 'They want to talk to a salesperson, so we should let them talk to a salesperson.' Well, we should find another way if they're a small business, because that's really just going to blow our cost structure out of the water."
For organizations between your self-serve and enterprise thresholds, consider what John calls "scaled touches" to help them grow: webinars, light-touch support, or enablement resources. At Canva, they created "Canva Coaches" (deliberately not called "sales") to help growing teams get more value from the product without the full enterprise sales experience.
The current state of CRO roles
We also discussed the changing landscape for Chief Revenue Officers. John believes we're in one of the most challenging periods for CROs, characterized by:
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Companies that did "more with less" during the recession now struggling to grow
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Board and investor expectations remaining high despite market challenges
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AI creating both opportunities and noise
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Bloated tech stacks that are underutilized
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Teams experiencing burnout from constant change
However, he sees this as a transformative moment: "I feel like the CROs that come out of this era are going to be different. What was required of a CRO 20 years ago is completely different than what is required today."
Today's successful CROs need to be more financially literate, aligned with product, and metrics-driven than ever before. The silver lining is that this difficult period is creating a new generation of more capable revenue leaders.
When evaluating career opportunities, John recommends focusing on:
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Stage fit (knowing where you thrive)
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Financial health and runway
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Solvable challenges within your control
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Team dynamics at the executive level
He suggests prioritizing company quality over title or scope: "Every time that I've seen acceleration in my career, a lot of times it wasn't those things [title and compensation]. It was probably a lateral move or taking a step back or maybe sideways. I might have taken a little bit of a haircut in comp, but the company and the product and the mission were so solid... If you do it that way, titles come pretty quickly all of a sudden. Pay actually starts to catch up to you because you're having a massive impact."
Final Thoughts
Adding a sales led growth motion to your product led growth foundation isn't a simple progression but a strategic transformation that requires careful planning and execution. The key is patience: waiting for clear signals, building in distinct phases, and structuring your team appropriately.
Most importantly, remember that what works for one company may not work for another. The specific implementation should be tailored to your unique market, product, and customer base. But the foundational principles John outlined remain consistent regardless of your industry or offering.
For more insights from John and to hear our full conversation, check out the latest episode of the Revenue Leadership Podcast wherever you listen to podcasts. And if you're finding value in these conversations, I'd appreciate it if you'd please leave a rating or review to help other revenue leaders discover the show!
