How to Build a Product-Led Growth Motion at a Sales-Led Company

At Tidemark, we spend a lot of time with founders building Vertical SaaS platforms. A recurring question we hear: can you layer product-led growth (PLG) onto an already-successful, sales-led go-to-market model?

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The short answer: yes—but only if you’re deliberate.

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When I joined Toast in early 2018, we already had a high-performing, field-based sales engine. Over time, we layered in a PLG and eCommerce motion that started as a small experiment and ultimately became a meaningful contributor to growth. By the time I left in 2024, this approach had meaningfully contributed to our new logo acquisition, helped us unlock new TAM, and shifted roughly 25% of our upsell transactions to a fully self-service experience—all without undermining our core sales motion.

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Here’s a practical playbook for founders looking to do the same.

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Why Toast Bet on PLG

When we started to explore PLG, Toast already had a proven and highly productive field-based sales model, but we also felt it was important to invest in new channels and unlock new TAM.  

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The push toward PLG at Toast wasn’t done on a whim—it was shaped by a convergence of trends that forced us to rethink how we engaged the market. The first and most obvious was COVID. Practically overnight, we had to adapt to a new operating environment where efficiency mattered more than ever. The “growth at all costs” mindset of 2018 and 2019 no longer applied, and we needed to challenge ourselves to do more with less.

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At the same time, we were beginning to see real momentum behind the Toast brand. After years of intense competition, we had gone from being an upstart to one of the most recognized names in restaurant technology. This dramatic increase in brand awareness gave us confidence that customers were open to buying from us in new ways.

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We also observed clear changes in buyer behavior. Existing competitors had already paved the way for self-service adoption, and nearly 1 in 4 restaurateurs—especially those just getting started—were now open to buying a point of sale online. These were customers we weren’t reaching through our traditional sales-led approach.

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And that’s what ultimately tipped the scales: the realization that PLG could help us reach an entirely new segment of the market. While we had built success serving larger, more complex restaurants, we lacked a focused go-to-market motion that was built for small, newer locations. PLG was our way to meet them where they were.

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Step 1: Define the Opportunity

In a previous post, I wrote about how critically important it is to place strategy before individual tactics. At Toast, we put this practice to work by focusing on the strategy and segment that PLG would unlock first before moving to tactics. 

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Before writing a single line of code, we started with market definition. 

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• Segment and size: We took advantage of our existing internal “market insights” capability to understand which segments were most likely to buy online, how large the market was, and how frequently they bought
• Targeting vSMB: One key insight from our research was a dramatic increase over time in the % of vSMB restaurants that were willing to buy online - it had increased to 1 in 4
• Paint the Target: As a result, we were able to explicitly call out who PLG would support and who it wouldn’t: ‍
  
  • Existing Sales-led motion: Larger restaurants familiar with legacy-systems‍
  • New PLG/eComm motion: Smaller, new restaurants familiar with cloud based systems 

This segmentation and refinement down to actual GMV bands helped us avoid internal conflict and optimize pricing & packaging later on.

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Step 2: Test and Scale Demand

Perhaps more importantly, now that we had the strategy figured out, we didn’t immediately invest in building a fully-formed PLG engine. Instead, we took a measured, experiment-first approach—focused on testing demand and validating whether a self-serve model would actually resonate with our target customers.

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We began with “painted door” testing—realistic-looking eCommerce flows that provided an artificial self-serve path to prospects in order to validate demand before investing in infrastructure. These prototypes had no backend functionality but were instrumental in gauging whether small restaurant operators were willing to engage with a digital purchase experience. The answer was yes, but that didn’t mean we were ready to scale just yet.

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As interest grew, we invested in self-serve experiences to accelerate activation and reduce onboarding costs. We also had to rethink pricing. Our legacy model (traditional SaaS + payments) simply didn’t land with smaller restaurants. After several iterations, we found that a usage-based model lowered the barrier to entry and unlocked demand.

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With those fundamentals in place, and once we had signal, we started investing in owned and paid channels to drive volume into the funnel. But we never lost sight of the sequencing: validate first, build second, scale last.

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If you’re a founder considering PLG, here’s what to focus on in this phase: 

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• Start with signal, not software: Use “painted door” experiments to test demand before investing in product or infrastructure.
• Rethink pricing from your buyer’s perspective: Smaller customers may not respond to your traditional SaaS pricing-–don’t be afraid to test and iterate here! 
• Invest in activation, not just acquisition: A self-serve funnel only works if customers can quickly go from sign-up to success. Onboarding matters. 
• Scale channels only after you’ve proven conversion: Volume before validation just burns cash. 

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At Toast, our PLG playbook ultimately helped us become more than a sales engine—it made us a more active participant in our customers’ daily workflows. That’s exactly the kind of transition Tidemark describes in their recent piece on “systems of action,” where PLG becomes a stepping stone toward delivering value directly at the point of work. If you’re looking to go deeper on how PLG connects to broader control point dynamics, it’s worth a read.

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Step 3: Navigate Internal Tension

This might be the hardest part—especially in a high-performing sales culture. New go-to-market models can feel threatening to teams that are already performing well, especially when compensation and territory ownership are at stake.   

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At Toast, we addressed this head-on. We spent real time with sales, finance, and product leadership to explain the “why” behind PLG, and to paint a clear picture of who this motion was built to serve. We also set clear ICP boundaries to ensure our sales reps weren’t competing with PLG. 

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We also aligned incentives early. Initially, sales reps received full compensation for any PLG deals that came from their territory. Over time, we transitioned to other commission models.

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Importantly, we treated PLG as more than just a new channel—it was a capability that could create durable value across the organization. From Toast Shop (our online storefront) to digital onboarding tools and trialing engines, many of the assets we built for PLG ended up benefiting other parts of the business.

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Here are the key lessons:

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• Over-communicate the “why.” Don’t assume teams will connect the dots. Explain what PLG enables—and what it doesn’t replace.
• Define clear ICP boundaries. Avoid internal competition by drawing firm lines between who PLG serves vs. sales.
• Align comp early. If reps feel like they’re losing commission to a new channel, friction is inevitable. Design your comp plans to reflect the full picture.
• Think beyond the PLG channel. The infrastructure you build—trial engines, onboarding flows, digital storefronts—can be reused across your GTM org.

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The Result?

A strong PLG motion didn’t happen overnight, but in time we saw this strategy lead to: 

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• Small restaurant bookings up 10%
• 25% of Upsell shifted to PLG
• Sales team focused on higher-value deals
• PLG opened up an underserved segment at attractive CAC/LTV

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PLG didn’t replace our sales motion—it expanded it.

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What This Means for Founders

If you’re building a Vertical SaaS platform, chances are your customers span a wide spectrum. The right PLG motion can help you reach the long tail efficiently, while giving your sales team more room to chase the whales.

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But it only works if you start with:

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• Clear ICP segmentation
• Ruthless testing before scaling
• Strong cross-functional alignment

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At Tidemark, we built the Vertical SaaS Knowledge Project (VSKP) to share strategies like this and more. If you’re thinking about PLG—or already wrestling with it—we’d love to hear from you. Reach out to knowledge@tidemarkcap.com or subscribe here to stay up to date with our latest thinking.