Ep. 172 - Why “Founder-Market Fit” Should Guide Your AI Go-to-Market Strategy

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Guest: Sammy Greenwall, Founder of Henry.ai -- 

What if your go-to-market motion could skip past theory and build from real-world pain? 

That’s exactly how Sammy Greenwall, founder of Henry.ai, approaches commercial real estate—and why his vertical AI startup is scaling without traditional sales or marketing. 

Sammy’s background as a CRE professional-turned-founder gave him not only insight, but language, trust, and distribution advantages. In this episode, he shares how founder-market fit drives everything from product strategy to GTM efficiency—and how it’s paying off in a space historically allergic to software.

Sammy also pulls back the curtain on:

• How PLG became a byproduct of customer obsession—not the plan
• Building a waitlist-worthy brand (with no ad budget)
• Creating real enterprise value in a low-trust, high-volume industry

Three Key Takeaways for B2B GTM Leaders:

1. Founder-Market Fit > Generic Product-Market Fit
Sammy’s deep domain experience gave him a faster path to traction: he didn’t just “identify” pain—he lived it. That meant smarter onboarding flows, tighter feature prioritization, and messaging that clicked with buyers the first time. CEOs and founders with industry-specific experience should lean hard into that unfair advantage.

2. PLG Isn’t a Tactic—It’s the Outcome of Product Obsession
Henry.ai didn’t set out to be a PLG company. Instead, they tracked usage down to individual clicks, met with every early user, and iterated daily. That intensity created a product people wanted to talk about, which fueled organic adoption, referrals, and even early enterprise wins.

3. AI Doesn’t Just Accelerate Work—It Replaces It
In CRE, Sammy’s platform cut multi-week deal deck creation down to hours. That kind of workflow disruption isn’t about “boosting productivity”—it’s about letting revenue-generating staff focus on high-value activities like deals and relationships. This shift reframes AI adoption for skeptical buyers and opens the door to premium pricing.

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