The AI Revolution in Commercial Real Estate: How Henry AI is Improving Deal-Making Workflows

Written by:

Steve Marcinuk

Date:

19 Aug 2025

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Commercial real estate professionals have long struggled with inefficient back-office operations that drain time and resources from deal-making activities. While the industry has historically been slow to adopt new technologies, the emergence of sophisticated AI solutions is changing how professionals approach their most critical workflows.

At the center of this shift is Henry AI, addressing one of commercial real estate’s most persistent pain points: the laborious process of creating pitch decks. What began as a focused solution to streamline collateral generation has evolved into a broader vision for improving commercial real estate operations.

From Family Business to Tech Innovation

Sammy Greenwall, CEO and Co-Founder of Henry AI, brings a unique perspective to the PropTech space. Raised in a commercial real estate family in the Bay Area and exposed to Silicon Valley’s technology ecosystem, Greenwall developed insights from both worlds.

“I grew up in a commercial real estate family, small commercial real estate investors in the Bay Area. I was also exposed to software and technology growing up in the Bay Area, so I got to do some pretty cool internships for large venture capital funds, and also some startups like Postmates,” Greenwall explains.

His experience as a commercial real estate analyst at Toll Brothers provided crucial insights into the industry’s operational challenges. “I had to build a lot of deal decks during that period, and that really got me passionate about commercial real estate,” he recalls. This experience, combined with exposure to venture capital, sparked his entrepreneurial ambitions.

After founding his first company, Lev, Greenwall took the lessons learned to launch Henry AI 13 months ago, applying a more focused approach to solving industry problems.

Identifying the Critical Workflow Bottleneck

Henry AI’s success stems from recognizing a fundamental inefficiency in commercial real estate operations: back-office processes were creating significant bottlenecks for professionals trying to close deals.

“What we identified super early on was that commercial real estate back offices are super, super inefficient,” Greenwall notes. “If you’re a commercial real estate broker or you’re an investor and you need to get a deal closed, you have to build this pitch deck. And this pitch deck is long, it’s arduous, it’s 50 pages, it takes weeks.”

The impact of these delays extends beyond inconvenience. “What we realized is that these commercial real estate professionals were literally losing money every day that this deck was being waited on, and they were building these on a very frequent basis,” Greenwall explains.

By focusing on this mission-critical workflow, Henry AI positioned itself as an essential tool. The company’s solution allows professionals to “launch their deals more quickly, close on more deals, and ultimately make more money and have a more efficient process.”

Strategic Focus Drives Rapid Adoption

Henry AI demonstrates the power of strategic focus in PropTech. Rather than attempting to solve multiple problems simultaneously, the company perfected its initial solution before expanding.

“We’re not going to be a deck making company forever. We did identify the right place and the right wedge to start, but there are so many different places that you can serve commercial real estate professionals,” Greenwall explains. The company has identified three key areas for future expansion: collateral generation, underwriting, and transaction management.

This focus has yielded impressive results. Henry AI now serves five of the top 10 US commercial brokerages and claims to be “the fastest growing AI native prop tech company by many miles.” The company has achieved this scale with a lean operation, servicing over 80 customers without traditional sales or extensive operations teams.

“If you find the right singular problem, even if it’s niche, and you do a really good job solving that problem, you can scale fast,” Greenwall observes. “Focus, focus, focus, think as narrow as possible, but as acute as possible.”

The Customer Obsession Philosophy

Central to Henry AI’s success is what Greenwall calls “customer obsession,” a philosophy that goes beyond typical customer service. This mindset involves daily evaluation of whether the product truly serves customers in powerful and positive ways.

“Customer obsession means going in every single day into your company and thinking about if the product that you’re building is serving them in an extremely powerful and positive way, and if it’s not, or where those gaps are, just being honest with yourself as soon as possible,” Greenwall explains.

This approach prioritizes product value over traditional metrics: “You don’t think about your ARR of course, those numbers matter. You don’t think about how much venture you raise. Those are all secondary metrics. If you put your customers first, and you actually don’t just say it, but believe it every single day, that is really what separates a good company from a great company.”

Technical Differentiation in an AI-Saturated Market

As general-purpose AI tools become more sophisticated, Henry AI maintains its edge through specialized technical architecture and industry knowledge. The company uses a multi-agent approach with hundreds of agents, each tasked with specific platform functions.

“Certain agents are responsible for data extraction, other agents are responsible for content generation. But even within content generation, some agents are responsible for summarizing the market in location overviews versus demand drivers,” Greenwall explains. “Being hyper focused on each specific niche within our niche gives us a product that horizontal solutions are not going to be able to copy over.”

Beyond technical architecture, deep understanding of commercial real estate workflows creates further differentiation. “When you’re building something for any kind of vertical, you really get to understand the workflows of the customers quickly,” Greenwall notes. “How deeply do you understand their workflow, and how deeply do you understand how they’re going to respond to your questions in the workflow, so that they’re giving you the right information long term.”

Changing Market Dynamics

The commercial real estate industry’s relationship with technology adoption is evolving. While the sector has historically been resistant to new solutions, AI tools have significantly changed the equation.

“It’s a lot easier to sell to a series A startup in San Francisco than it is to a commercial real estate investor in southern Texas,” Greenwall acknowledges. “But the difference today versus what you saw previously is that the value that you can drive for these commercial real estate professionals is entirely different than what it was even three or four years ago.”

The shift from incremental productivity gains to complete workflow replacement has transformed buyer behavior: “It was really hard to sell software to someone when you were making them 20% more productive, but when you’re fully replacing the work 100% and the work is better, the value proposition has just totally changed.”

The Future of Work in Commercial Real Estate

Henry AI’s approach raises important questions about the future of work in commercial real estate. While Greenwall acknowledges that some job displacement is inevitable, he sees the transformation as more nuanced than simple replacement.

“Jobs are going to be replaced. I don’t think that it’s going to be an Armageddon where everyone loses their role, but the most laborious and repetitive job descriptions today are probably going to be replaced over the near term,” he explains.

However, this displacement comes with opportunities: “People who are still in commercial real estate are going to be supercharged. They’re going to be 10x more efficient and productive. Also, people within commercial real estate are going to be able to move towards relationship management and sales and non-menial tasks quicker.”

The challenge lies in maintaining institutional knowledge and training: “If Henry is doing the deck making, and you’ve got another product doing the underwriting, how do you train the next generation? You do need to know how to do underwriting at some point in order to understand the business long term.”

Looking Forward

As Henry AI expands beyond pitch deck creation into underwriting and transaction management, the company represents a broader trend toward specialized AI solutions that deeply understand industry workflows.

The success of Henry AI demonstrates that in the current AI landscape, technical sophistication alone isn’t sufficient. Companies that combine advanced AI capabilities with deep industry expertise, customer obsession, and strategic focus are positioned to capture significant market share in technology-resistant sectors.

For commercial real estate professionals, the message is clear: AI tools are no longer experimental add-ons but essential components of competitive operations. The question isn’t whether to adopt these technologies, but how quickly organizations can integrate them while maintaining the human expertise that drives successful deal-making.

As the industry continues to evolve, companies like Henry AI are proving that the future of commercial real estate lies not in replacing human expertise, but in amplifying it through intelligent automation of routine tasks, allowing professionals to focus on what they do best: building relationships and closing deals.