Entering his second year as president and CEO of Re/Max, Bailey enters the top 10 of the SP 200 for the first time in 2024. As head of the storied real estate brand, he leads approximately 58,000 U.S. agents who do over $290 billion in annual sales.

Among his most notable achievements in 2023 includes the $55 million settlement he helped secure for Re/Max in relation to the class-action antitrust compensation lawsuits. The settlement, pending court approval (anticipated in early 2024), allows the brand and its many affiliates to operate without that legal uncertainty hanging over their heads in 2024.

In addition, the brand reported a strong second half of 2023, reporting that it sold 45 U.S. franchise sales (including an additional nine in Canada) in the third quarter, eight more than the 37 it sold in the second quarter.

A veteran industry leader with executive experience at Zillow and Century 21 Real Estate, Bailey has his work cut out for him in 2024, the recent franchise sales notwithstanding. The company has steadily lost U.S. agents in recent years. For example, from June 30, 2022, to June 30, 2023, Re/Max lost 6.3% of its U.S. agents.

The brand continues to grow globally, which falls within Bailey’s purview. But it has been shrinking in the U.S., something Bailey and team will need to address to maintain their performance and dominant position (the company makes significantly more revenue from U.S. operations than internationally).

Based on the brand’s momentum, and its leadership in relation to securing a settlement agreement for the compensation lawsuits, Bailey is the 10th most powerful leader in real estate in 2024.