Henry AI, a commercial real estate startup, has raised a $16.5 million Series A to automate the analyst work behind property deals, cutting a task that once took 15 hours down to 30 minutes of review. The round was joined by Thomson Reuters Ventures, Susa Ventures, 1Sharpe Ventures, Y Combinator, and Coalition Operators.
The clearest sign of what Henry has built came not from its founders but from a customer. Asked about the product, a top Marcus & Millichap broker admitted, “I don’t want too many people to know about this.” When customers start hiding a tool from their competitors, the demand question answers itself.
For decades, commercial real estate ran on human labor as its software: analysts hand-building the financial models, memos, and client-ready deliverables behind every transaction. Henry inverts that. Rather than helping analysts organize the work, its AI does the work, generating the deliverables directly and leaving a person to review instead of assemble.
The founders, Sammy Greenwall and Adam Pratt, have taken the platform to more than 150 firms in two years, including four of the five largest US brokerages, with over 20,000 client-ready deliverables produced behind roughly $150 billion in deal value.
The Series A is notable for another reason: the investor leading it publicly admitted he once told Greenwall and Pratt not to start the company, citing a historically brutal market for real estate software, before backing them two years later.
That reversal captures a wider shift. As AI moves from organizing work to performing it, industries long considered too labor-heavy or too cyclical for software, from law to finance and now commercial real estate, are being rewired one professional workflow at a time. Henry is betting it can be the teammate, not the tool, that leads that change in CRE.
We called it early in Big Law and on Wall Street. Commercial real estate is next, and we’ll be watching. Tech Lens Media.
Source: Upstarts Media / Alex Konrad.