Diane Glass

Chief Executive Officer, Berkshire Hathaway HomeServices Chicago

Glass is at the helm of a familiar institutional brokerage in an industry filled with nimble upstarts eager to disrupt the status quo.

Glass stepped into BHHS Chicago’s CEO role in July 2020 as the brokerage navigated pandemic disruption and a shifting competitive landscape. She oversees a firm with roughly 1,500 agents across more than 20 offices spanning Chicagoland, southern Wisconsin and northwest Indiana.

It has seen mixed results in the evolving brokerage landscape. BHHS Chicago ranked sixth in The Real Deal’s 2025 brokerage rankings with $1.5 billion in volume, but the firm has also seen market share erosion and high-profile departures. Top producer Mario Greco left for Compass in 2024, and senior executives Joe Stacy and Mark Pasquesi exited in subsequent years.

Glass built her career on training and education, holding senior instructional roles at Coldwell Banker and Koenig & Strey before her current role. Since taking the top job, she has leaned into that background, emphasizing agent development while also expanding the firm’s physical footprint with new offices in neighborhoods like Andersonville and suburbs including La Grange and River Forest.

Glass, who also serves as president of BHHS Chicago’s title company, Fort Dearborn Title, continues to push a training-first strategy as the brokerage fights to retain talent amid intense recruiting pressure.

— Caleb McCullough