Henry AI Raises $16.5M Series A for CRE Deal Platform
Henry AI, a New York-based AI platform for commercial real estate brokers, has raised $16.5 million in Series A funding led by FirstMark Capital. The platform automates underwriting models, comps research, and institutional pitch decks from a sentence and rent roll. The round also included participation from Thomson Reuters Ventures and follow-on investors.
FirstMark Leads After Initial Skepticism
The timing aligns with accelerating AI adoption in CRE brokerages facing back-office bottlenecks. Henry previously raised $4.3 million in seed funding in February 2025. Lead investor Adam Nelson initially advised against targeting CRE brokers but later joined the board after seeing traction.
Manual Deck Creation Drains Broker Time
Brokers traditionally spend 15 to 30 hours building a single deal deck or offering memorandum. The process involves pulling comps, building Excel models, and formatting branded presentations. This manual labor limits deal volume and forces firms to maintain large support teams even as transaction activity rebounds.
Vertical Workflow Replaces Generic Tools
Henry ingests a firm's own historical deals and CRM data to generate underwriting, ranked comps, and pitch decks on the brokerage's brand. The system operates through email and Excel add-ins without requiring logins, lowering adoption friction for time-pressed brokers. It differs from competitors like Blooma, which focuses on lender-side underwriting, and Archer, which targets multifamily analysis without buyer list generation.
As Sammy Greenwall noted in coverage:
"Every deal in commercial real estate is buried under a pile of documents that someone had to make by hand."
FirstMark and Thomson Reuters Validate Vertical Bet
FirstMark's portfolio includes high-growth SaaS companies such as Shopify and Discord. Thomson Reuters Ventures joined as a strategic investor, signaling interest in workflow automation for professional services. Existing backers including Susa Ventures, Y Combinator, and RXR also participated.
CRE Brokerages Adopt AI to Scale
More than 150 firms, including four of the top five U.S. brokerages, now use the platform. Henry has processed over 20,000 deliverables tied to $150 billion in deal value. Twenty percent of customers have reduced staffing as a direct result. The company reached $3 million ARR within 16 months of launch.
Leadership Draws on Prior CRE Experience
CEO Sammy Greenwall previously co-founded Lev, a CRE financing platform that raised $100 million across Series A and B rounds. The founder-market fit informs product decisions around institutional output and workflow integration.