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.

Watch the video here.

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting