Over his two decades as CEO of Redfin, Kelman guided the company to its position as a top 10 brokerage and portal behemoth. While he sought a sustainable way to operate and grow an employee-based brokerage, after years of profitability challenges, he helped orchestrate the sale of the company to mortgage giant Rocket in 2025 for $1.75 billion — an amount roughly double Redfin's enterprise value at the time. Kelman, a passionate leader who remains at the helm of the company, has also been outspoken about his belief in an open, comprehensive marketplace, endorsing Zillow Group’s decision to reject listings that had been publicly marketed but not widely available through the MLS or national search portals.