Henry AI Raises $16.5M to Automate CRE Transaction Documents

Henry AI Inc. has closed a $16.5 million Series A financing round to scale its artificial intelligence platform that automates document production across commercial real estate transactions, the company announced.

FirstMark Capital led the investment, with strategic backing from Thomson Reuters Ventures. The round also included participation from Y Combinator, Susa Ventures, 1Sharpe, StoryHouse Ventures, Pioneer Fund, RXR Arden Digital Ventures, Karman Ventures and Coalition Operators. FirstMark partner Adam Nelson has joined Henry's board of directors.

Adoption across major brokerages

The platform is currently deployed at more than 150 firms, including all of the largest commercial real estate brokerages, according to Henry. The technology handles document-intensive tasks such as offering memorandums, underwriting analyses, pitch decks and buyer lists.

Henry reports it has generated over 20,000 client-ready deliverables tied to more than $150 billion in transaction value. The company's automation has reduced analyst production time by 90%, compressing work that previously required an estimated 15 hours per deliverable to approximately 30 minutes of human review. Platform-wide median turnaround time is under four hours.

More than 20% of Henry's customers have reduced staffing requirements after implementing the platform, the company said.

Why it matters

Commercial real estate transactions remain heavily manual despite the industry's scale, with junior analysts spending days formatting documents that follow predictable patterns. Henry's metrics suggest AI can now handle this production work reliably enough that firms are adjusting headcount — a concrete signal that automation is moving beyond pilot projects into operational infrastructure. The planned expansion into a system of record positions the company to capture institutional knowledge that has historically lived in spreadsheets and email threads.

Expansion into deal management

Henry plans to deploy the new capital to grow its engineering and product teams and evolve the platform into a comprehensive system of record for commercial real estate deals.

The company will launch Henry Deal on June 15, a product designed to organize firms' historical underwriting models, transaction records and client relationships. The system will then leverage that institutional data to generate materials throughout a deal's lifecycle.

"Every deal in commercial real estate is buried under a pile of documents that someone had to make by hand," co-founder and CEO Sammy Greenwall said. "But the documents are just the surface."

Co-founder and Chief Technology Officer Adam Pratt framed the company's approach around execution rather than data access: "The bottleneck in CRE has never been the data — it's the cost of turning data into finished deliverables."

These details were first reported by Connect Money.