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

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. TOPICS 00:00 – Introduction 01:39 – The Genesis of Henry AI and Early Conversations 03:00 – Sammy’s Background: From the Bay Area to Toll Brothers 03:53 – The Pain Point: Spending 70% of the Day in PowerPoint 07:41 – The Lev Story: Starting a Company with a Rabbi in a Chabad House 11:00 – Scaling to a $100M Series B and "Relentless Grit" 13:10 – Leaving Lev to Build a Generational AI Company 15:18 – Why Brokerage Costs Are Under Fire 18:00 – Why Henry Charges 3x More 19:50 – Why the Professional Touch in AI Still Matters 21:56 – Identifying the Single Pain Point 24:08 – The Future of Interactive, Digital Offering Memorandums 27:19 – The Data War 32:58 – Labeling the "Walled Garden" of Commercial Real Estate Data 35:30 – Where the Name "Henry" Actually Came From 38:14 – CEO Productivity For more episodes of No Cap by CRE Daily visit https://www.credaily.com/podcast/ Watch this episode on YouTube: https://www.youtube.com/@NoCapCREDaily About No Cap Podcast Commercial real estate is a $20 trillion industry and a force that shapes America’s economic fabric and culture. No Cap by CRE Daily is the commercial real estate podcast that gives you an unfiltered ”No Cap” look into the industry’s biggest trends and the money game behind them. Each week co-hosts Jack Stone and Alex Gornik break down the latest headlines with some of the most influential and entertaining figures in commercial real estate. About CRE Daily CRE Daily is a digital media company covering the business of commercial real estate. Our mission is to empower professionals with the knowledge they need to make smarter decisions and do more business. We do this through our flagship newsletter (CRE Daily) which is read by 65,000+ investors, developers, brokers, and business leaders across the country. Our smart brevity format combined with need-to-know trends has made us one of the fastest growing media brands in commercial real estate.