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The Long View

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

Tidemark Venture Partner and former CMO at Toast, Kevin Hamilton, shares insights from Toast’s journey from $40M to $1.2B in ARR

Kevin HamiltonTidemark Operating Partner and Former CMO

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?

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

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.

At Tidemark, we try to open-source our thinking as much as possible to help founders win; however, as investors, we can’t give everything away in public. If you’re an operator or founder, you can request access to the rest of this piece below.

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