Henry Raises $16.5M to Automate Commercial Real Estate Deals
Henry (henry.ai) has raised a $16.5 million Series A led by FirstMark Capital, with participation from Thomson Reuters Ventures, Susa Ventures, Y Combinator, Pioneer Fund and others. Susa, Pioneer Fund and 1Sharpe backed the company's $4.3 million seed in early 2025. The round was reported first by Upstarts Media, which noted it was closed quietly last fall.
Henry sells software to commercial real estate brokers that turns rent rolls, comps and deal notes into the marketing and analysis materials a transaction requires. Alongside the funding, the company is launching Henry Deal, which extends the platform from deck production into comps research, underwriting, buyer lists and memos, run by agents rather than assembled by an analyst.
Co-founders Sammy Greenwall and Adam Pratt started the company in 2024 and went through Y Combinator that summer. Greenwall co-founded CRE financing startup Lev and served as its chief revenue officer before leaving to build Henry. Pratt co-founded Halligan, a software platform for fire departments, which Vector Solutions acquired in 2019.
The first product went after the marketing package a broker needs before taking a property to market, branding and maps and data included. Henry says that work runs a designer about 15 hours and that its median turnaround is under four, roughly half an hour of which is human review. More than 150 firms use it, including Newmark and Berkadia, and its customers include four of the country's five biggest brokerages. Pricing starts at $2,000 a month and rises into seven figures with usage.
"The real problem was never the documents. It was the hours."
Sammy Greenwall, CEO of HenryGreenwall says more than $150 billion in deal value has run through the platform and that revenue has nearly tripled since the round closed. The company says more than a fifth of its customers have trimmed back-office staffing after adopting it.
Henry Deal reached test users in June. A broker gives it a description of the deal and a rent roll, and the platform runs the underwriting, pulls comparable sales, drafts the research and produces the pitch materials on the firm's branding. It is built to switch between models depending on the task rather than sit on one provider.
Pratt told Upstarts that working out how a given industry actually absorbs the technology, rather than building the models themselves, is the unresolved part of the current AI cycle.
"We're at the forefront of what I would call the hard part of AI."
Adam Pratt, CTO of HenryAdam Nelson, a partner at FirstMark, led the round and has joined Henry's board. In a post on the investment, Nelson wrote that he advised Greenwall against starting the company when the two met during the 2024 batch, a view that rested on brokers being a difficult group to sell software to, according to Upstarts' account of the meeting. Henry went on to reach most of the largest brokerages in the country, and Nelson now puts the platform's output at more than 20,000 client-ready deliverables, writing that the firms getting the most out of it are using it to pursue more deals with the same people rather than the same volume of work with fewer.
Greenwall sums up the roadmap as "winning the deal today, the entire back office tomorrow."