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  • Writer's pictureAndre Watson

Compass taps former Corcoran exec to lead Hawaii outpost Bill Cunningham to lead sales in Aloha Stat

Bill Cunningham (Compass, iStock)

Compass has been keeping busy in Hawaii.

With a busy ultra-luxury market reaching new heights, the company has tapped Bill Cunningham as managing director of sales in the Aloha State.


Cunningham, who stepped down as president of sales at Corcoran in 2019, has in recent years pursued work with private investment groups and fix-and-flips in his spare time.


“I realized this investment thing was not enough,” Cunningham said. “I’m used to the 24/7 real estate industry, it’s kind of in my blood.”

Cunningham joined Corcoran in 2001 and worked his way up to managing 2,600 agents across all markets, including New York City, Palm Beach and the Hamptons. He left the firm in 2014 for an eight-month stint as president of Trump International Realty before returning to Corcoran.


Compass expanded to Hawaii in 2020, just in time to capitalize on the state’s booming “ultra-luxury” market of homes at $10 million or more. The market last year reached 78 homes sold and $1.1 billion last year, more than double the previous year’s sales volume.

Since its arrival in Hawaii, Compass says it has closed on more than $2.3 billion across the state and has opened offices on every major Hawaiian island. The company’s Maui office ranked sixth industry-wide in sales volume.

“I don’t see it changing any time soon,” Cunningham said of the state’s high-end real estate market. “I think people are starting to notice Hawaii more and I’m seeing more nonstop flights from those areas of the country so it just makes sense.”

Compass expanded into 25 additional markets last year, the firm reported, growing its national market share to 5.6 percent, up from 4 percent in 2020. Its agents closed 56,912 transactions — a 20 percent year-over-year increase.

Despite its growth, the company reported a loss of $175 million in the fourth quarter of last year, up from the $100 million lost in the third quarter and $40 million in the same period in 2020. Its record recruiting period came with an 80.3 percent increase in operating expenses to a whopping $6.9 billion.

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