From Busywork to Business: Why We Led Henry’s Series A

My first job out of school was as an analyst. I spent nights nudging logos around a slide one pixel at a time and rebuilding version 78 of a book at 3AM for a meeting where the client might never open it. Every deal business runs on the same journey: raw data becomes a finished deliverable becomes a human decision. For fifty years, the only bridge across was people. Workflow software never changed that. It handed the analyst a slightly better wheelbarrow and called it transformation.

An Oregon Trail market

When I was getting started in venture, a mentor of mine had a name for categories like this: "Oregon Trail" markets. You ride out full of conviction, and the whole way there the trail is littered with the wagons of everyone who tried before you. Commercial real estate software is the classic of the genre. Brokers don't buy tools, and the category is a junkyard of point solutions with unclear ROI.

I believed this so completely that when Sammy Greenwall pitched me during Henry's YC batch in 2024, I told him not to build the company. You seem like a smart guy, I said, and this is a terrible customer base to sell through.

I wasn't wrong about the market historically. A broker is effectively an independent operator whose only inventory is time, and nearly every tool ever sold to them asked for more of it. Hiring an analyst to just do the work was the smarter buy. In commercial real estate, labor was the software.

What I got wrong was treating that as a fact about the market instead of a fact about the products being sold to them. The question was never how to sell this industry more software, it was how to give brokers their time back, and that required a product that does the work rather than organizes it. That product was impossible until late last year, when AI crossed its agentic threshold. The same leap that let models stop suggesting code and start shipping it is what lets Henry take a set of financials and hand back a finished, branded, client-ready package. We're operating under an entirely new technology paradigm, and yes - selling into commercial real estate is still an Oregon Trail market, but the wagons we're riding have been upgraded to self driving cars.

Fording the river

Teams from every one of the largest brokerages in the country are on Henry today, more than 150 firms in total. The thesis of selling the work is alive and well, and as a platform, Henry has produced over 20,000 client-ready deliverables representing more than $150 billion in underlying deal value. Work that took an analyst 15 hours now takes about 30 minutes of review, with a median turnaround under four hours.

The largest firms in the industry are not experimenting with Henry. They are running on it.

And the way they talk about it says more than the numbers. Brokers at the industry's top firms describe Henry as a new teammate. During our work on the space, a veteran broker at one of the largest firms told us Henry solved "a 17-year daily anxiety" of preparing packages for incoming work. Nobody talks about their CRM that way. That's how you talk about a colleague. We've watched the same shift play out in legal services and on Wall Street, including inside our own portfolio. CRE is next, and Henry is out in front.

Sammy and Adam

Commercial real estate is a relationship business run by people who can smell an outsider instantly, and it punishes tourists. Sammy Greenwall isn't one. He already built and scaled a venture-backed company in this industry, and he knows the buyer, the workflow, and the politics of a deal cold. He also heard my skepticism in 2024 and kept building anyway, which tells you most of what you need to know about him and his conviction on the opportunity. Adam Pratt brings the other half: real engineering pedigree wired to the curiosity, intensity, and hacker instincts of the best of YC.

The pairing is the engine. Sammy's credibility with this industry gets him to the core of what clients actually want, and he translates that into what to build. Adam's team gets it into customers' hands in weeks, not quarters. Everyone has access to the same models now, so the moat is how fast industry knowledge becomes a working product, and we have rarely seen a team convert faster.

From making decks to doing deals

A brokerage's revenue is capped by one constraint: the hours its brokers spend winning and closing business. Every hour in production is an hour not spent originating, and in this industry origination is everything. Up to a third of commercial transactions never hit the open market. They're won through relationships, and relationships are built in exactly the hours that production work consumes.

The firms getting the most out of Henry aren't using it to do the same work with fewer people. They're using it to chase more work with the same people. One broker put it plainly: Henry lets his team "focus on selling properties versus constantly making proposals." That's the trade this industry has been waiting decades to make.

Henry Deal, launched in June, extends this across the entire lifecycle of a transaction, from underwriting to packaging to close, built from a firm's own institutional knowledge. But the right way to understand it isn't as a place where brokers go to do the work. It's the teammate they send the work to while they're out building the business. Sammy says it best: "Winning the deal today, the entire back office tomorrow."

We're thrilled to lead Henry's $16.5M Series A alongside Thomson Reuters Ventures, Y Combinator, Susa Ventures, 1Sharpe, and others. We believe Henry becomes the system CRE firms rely on to underwrite, win, and execute deals, and over time, the intelligence layer for commercial real estate.

Two years ago I told Sammy this company shouldn't be built. Leading its Series A, on the strength of this team and the customer love we saw everywhere we looked, is my favorite way to admit I was wrong. Excited to build what's next with Sammy, Adam, and the whole Henry team!