A broker’s success is based largely on interpersonal skills, yet those skills can be undercut by the time and effort required to complete the manual tasks that are essential to getting a deal done. The dynamic is similar for sponsors looking to bring in limited partners and finding that the hours it takes to put together deal decks are hours that could be better spent in meetings with investors.
To accelerate the process for brokers and sponsors in a world where both speed and polish matter, CEO Sammy Greenwall and cofounder and CTO Adam Pratt founded Henry AI in 2024. It’s a copilot designed to turn raw data into finished deal decks—rapidly—and has since become an everyday tool for some of commercial real estate’s most prolific dealmakers. ApartmentBuildings.com sounded out Greenwall on how AI can make a substantial improvement in the process of winning those deals.
Q: With transaction volume still uneven across sectors, where do you think firms can gain the biggest competitive edge right now—relationships, data, speed, or creativity?
A: It’s a false choice — relationships still win deals, but the firms pulling ahead right now are the ones using data and speed to make their relationships more productive. When volume is uneven, the bottleneck isn’t who you know, it’s how quickly you can show up with a credible point of view. The brokers winning mandates today are the ones who can turn around a thoughtful pitch in hours instead of days, with comps and underwriting that actually hold up. Creativity matters at the margins, but the baseline has shifted: if you’re slow or your numbers are sloppy, the relationship alone won’t carry you anymore.
Q: What parts of the CRE transaction process will look completely different in three years?
A: The pre-pitch phase. Today, winning a deal still involves analysts spending nights pulling comps, formatting decks, and stitching together market data from five different sources — at most mid-market shops, that pre-pitch work eats the majority of an analyst’s week. In three years, that whole layer collapses. The intelligence work that happens before a broker ever meets the client will be largely automated, and the human time will shift to judgment, positioning, and relationships. The OM and pitch deck won’t disappear, but they’ll be artifacts of a much faster, more intelligent process underneath. The firms that adapt will spend more time on strategy and clients; the ones that don’t will keep paying analysts to do work that software does better.
Q: What advice would you give to a brokerage or investment firm leader who knows AI matters, but hasn’t yet taken the first real step?
A: Stop trying to have an AI strategy and just pick one painful workflow. The leaders I see making real progress aren’t the ones with twelve-month transformation plans — they’re the ones who said, “our team spends 30 hours a week on lease abstraction” or “on market reports” and went and solved that. Pick something measurable, give it to a small team, and let them ship something in 60 days. You’ll learn more from one real deployment than from a year of vendor demos. And don’t wait for the perfect tool — the cost of moving slowly right now is much higher than the cost of picking something imperfect and iterating.
Q: Today’s investors expect cleaner data, sharper visuals, and faster responses. How are expectations from buyers and capital sources evolving?
A: The bar has moved in two directions at once. On the surface, yes — buyers expect institutional-quality materials from everyone now, not just the top shops. A scrappy regional broker is being measured against the same visual and data standard as JLL or CBRE. But underneath that, the deeper shift is around speed and substance: capital sources want answers to their diligence questions in hours, not days, and they want the underwriting to be defensible the first time. The firms still treating an OM as the finished product are missing it. The OM is now table stakes; what differentiates you is how fast and intelligently you can respond to everything that comes after it.
Q: You’ve grown quickly in a traditionally slow-to-change industry. Why do you think the timing is right now?
A: A few things converged. The technology genuinely got good enough — two years ago, AI couldn’t reliably produce institutional-quality CRE work, and now it can. The market pressure helped, too: when transaction volume tightened, firms had to actually look at where their analysts’ time was going, and the answer was uncomfortable. The industry isn’t slow because the people are slow; it was slow because the tools weren’t there. They are now, and adoption is moving faster than anyone outside CRE realizes.
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