The Back Office is Dying with Henry AI's Sammy Greenwall

The Back Office is Dying with Henry AI's Sammy Greenwall

June 7, 2026 · 40 min · Season 7 · Episode 6

About this episode

Sammy Greenwall discusses the impact of AI on commercial real estate and his journey in building Henry AI.

Season 7, Episode 6: How did a former real estate analyst turn the pain of building pitch decks into one of CRE's fastest-growing AI companies?Today, we sit down with Sammy Greenwall, co-founder and CEO of Henry AI, to discuss how artificial intelligence is transforming commercial real estate workflows. Sammy shares his journey from college basketball to helping scale Lev into a $100M venture-backed company before leaving to build Henry AI.The conversation covers the inefficiencies of traditional brokerage workflows, why Henry focuses on delivering outcomes instead of software, and how AI is automating offering memorandums, BOVs, and other time-intensive tasks. Sammy also explains why local brokerage data may be more valuable than national databases, how "humans in the loop" remain critical to adoption, and where he sees the future of AI in commercial real estate.Shoutout to our sponsor, Henry AI. The fast track to investor-ready decks that actually stand out.TOPICS00:00 – Introduction01:39 – The Genesis of Henry AI and Early Conversations03:00 – Sammy’s Background: From the Bay Area to Toll Brothers03:53 – The Pain Point: Spending 70% of the Day in PowerPoint07:41 – The Lev…

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Guest: Sammy Greenwall

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Henry AI

Mentioned in this episode

Organizations: Henry AI, Lev, Toll Brothers, CRE

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