"AI Will Transform Transaction Management But Won't Replace Human Relationships,"Says Windermere President

Written by:

Steve Marcinuk

Date:

19 Jun 2025

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The real estate brokerage model is facing unprecedented change as artificial intelligence reshapes traditional tasks, but human relationships will remain central to success, according to one industry veteran.

“It’s not hard today. It’s hard looking into the future,” says OB Jacobi, President of Windermere Real Estate, discussing the evolving role of brokerages. While current operations are clear, the integration of AI and changing consumer behaviors are forcing brokerages to reimagine their value proposition.

The AI Revolution in Transaction Management

Jacobi points to transaction management as a prime example of where AI could transform traditional brokerage operations. “Our managers and owners spend a lot of time looking through contracts saying, ‘Hey Joe agent, you missed this blank,'” he explains. While this review process has educational value, Jacobi questions whether it’s the best use of human resources.

“We’ve never been sued on a contract… but we spend an inordinate amount of time looking through them,” he notes. “Is that a task that can be read really quickly with an AI behind you, and then managed in a different way?”

Shifting Consumer Behaviors

The transformation extends beyond back-office operations to how consumers interact with real estate information. Jacobi cites Google’s first usage decline in 25 years as evidence of changing search behaviors: “Are they going to complexity, or ChatGPT, or whatever? People are starting to do something different.”

This shift raises fundamental questions about traditional brokerage digital presence. “Are we going to have a website in the future? Is that going to be all things served on the AI platform?” Jacobi asks. “I think you’d be silly to bury your head in the sand and say it’s not evolving that quickly.”

The Human-Centric Future

Despite technological advancement, Jacobi maintains that personal relationships remain crucial to real estate success. “The very best agents in the world, typically… aren’t heavily invested in the tech. They’re heavily invested in their people,” he observes.

This insight shapes Windermere’s approach to agent support. “We need to support our agents with as much service as we possibly can,” Jacobi explains. “If we can help manage it, then let’s help you be successful without doing all the crap that goes along with being an agent.”

A New Support Model

The brokerage role has evolved significantly from the “Glengarry Glen Ross”era of total control to today’s agent-centric model. Jacobi sees the future as increasingly focused on comprehensive agent support.

“We feel like, if we can help – we’re not going to steal your database – if we can help manage it, then let’s help you be successful,”he says. “It’s hard enough being an agent rather than doing being the head marketing tech and all that.”

Looking ahead, Jacobi believes brokerages must balance technological innovation with maintaining focus on human relationships. “Our job as owners and managers of this business is to really try and stay on it and help our brokers… so they don’t have to be experts in AI.”