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Baird & Warner prepping Chicago agents to take on Goliath Compass

Brokerage gets candid about massive size of competitor by unveiling “City Collective initiative” aiming to unite 800 city agents

Baird & Warner's David Bailey

Baird & Warner is launching an initiative to bring more cohesion and tools to its Chicago-based agents as it seeks to stand out in a market against growing consolidation and national brands. 

The brokerage with strong suburban footholds nearly doubled its agent count in the city of Chicago when it acquired Dream Town earlier this year, it said in a press release. The new initiative, called the “City Collective,” will help unite its 800 city agents and give them new communications lines, tools and technology to compete, the company said.

Most of Baird & Warner’s volume currently stems from outside the city proper: About 65 percent of the sales volume between Baird & Warner and Dream Town year-to-date happened in the suburbs and outside Chicago, according to data provided by a spokesperson.

The focus on ramping up sales in the city will help Baird & Warner’s operations across the board, according to an interview with David Bailey, Baird & Warner’s senior vice president and general sales manager. Migration between the city and suburbs is a large factor in the market, and having a bigger focus on the city can help the firm capture more of the market, he told The Real Deal.

“Historically, we’ve been able to serve the entire Chicagoland community very effectively,” he said. “The relationships between our suburban brokers and our city brokers are only going to get deeper now.”

Baird & Warner, which has had a Chicago presence for 170 years, also used the initiative to take shots at its biggest competitor, Compass, which acquired homegrown @properties last year to become the largest Chicago brokerage by far. Compass also intends to take over Anywhere Real Estate, which would bring several more of Chicago’s top brokerages under Compass’s umbrella.

Baird & Warner is the largest independent brokerage in Chicago, and combined with Dream Town’s performance would have came in second in The Real Deal’s rankings of top brokerages by Cook County sales volume in 2024, after the combined volume of Compass and @properties.

Baird & Warner framed the initiative as a way to make the independent firm stand out against “Wall Street-run firms,” and the press release criticizes Compass specifically. It’s the second time in recent weeks the local firm has directly bashed the national giant in public communications materials.

Bailey said private exclusive networks like Compass’ marketing models are bad for consumers, noting Baird is a transparent alternative. Compass has pushed for a marketing strategy in which some properties start out marketed internally only to other Compass agents.

“It’s being veiled in innovation and some impressive new marketing approach, but I don’t think it’s about that. I think it’s just about control,” Bailey said. “And they’re not looking to serve the consumer, they’re looking to get both sides of the deal.”

Compass has defended its private marketing strategy as an option that gives sellers more choice in how to market their homes. In a statement, Compass spokesperson Devin Daly said the firm “thinks homeowners should be able to choose the best strategy for selling their homes.” He pointed to Compass research that found pre-marketed homes brought in higher closing prices and sold faster after hitting public networks.

Compass has made its own technology suite a cornerstone of its sales pitch to brokers, including a tool announced this week that it says will help listing agents find potential buyers in the Compass network based on buyer activity and search data.

Baird & Warner didn’t give specific details about the new tools coming for its agents under the City Collective program. Its press release noted new technology and AI tools, new internal communication tools and listing and marketing strategies. The company also said the initiative would give agents updates on local regulations, neighborhood trends and conduct regular meetings across its city brokerages. 

Bailey said the suite of tools would include “additional enhanced marketing opportunities” and a tech stack, and that they would be released over the rest of this year and early 2026. He said the tools will combine the data and AI expertise of Baird & Warner with the marketing and technology tools of Dream Town into a more cohesive product.

“Combining those two together is what’s going to allow us to take a big step forward,” he said.

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