Of all of the business discussions that Chad Cohen has had over the years, few are likely as memorable as the 20-second conversation he had with Zillow CEO Spencer Rascoff about midway into his 9-year career stint with the online real estate company. Cohen joined Zillow back in 2006 as corporate controller, a position that he says also had the added distinction of being the company’s first full-time finance role. Over the next 4 years, as Zillow’s back-office finance and accounting team took shape, Cohen’s responsibilities grew, allowing him to step into the role of vice president of finance. “I had been moving up the ladder, and it was right before we made the decision to go public—I remember Spencer coming into my office and saying, ‘You’re going to be CFO,’” says Cohen, who recalls Zillow’s CEO saying little more before exiting. For Cohen, the exchange signaled a 6- to 12-month transition that would enlarge his focus from being largely back-office to being both back- and front-office. “I had built an accounting and finance department, but this was a big step that required coaching from mentors and formal media training and IR experience,” says Cohen, who today views the Zillow IPO as only one of several Zillow milestones during his CFO tenure with the firm. Says Cohen: “I spent 4 years—or 16 earnings calls—as CFO, acquired about 10 companies, and raised somewhere between a half-billion and a billion dollars in capital from the public markets for Zillow Group.” Asked to recall a learning moment from his CFO years, Cohen says that he recalls waking up in a cold sweat during the 20- to 30-day period that immediately followed Zillow’s 2015 acquisition of Trulia. Having carefully crafted a 90- to 120-day postmerger integration plan, Cohen says, he realized that as the number of Trulia employee departures began to quickly escalate, “speed of integration” was going to play a plus-size role in the merger’s success. “Our retention bonuses—albeit very healthy and robust—were being offset by a very frothy employment market in San Francisco and even larger sign-on bonuses that we were having trouble competing with,” recalls Cohen. “I called my controller in a panic and said: ‘Hey, we have to do this faster because I think I see how the scenario is playing out—and it ain’t going to be pretty,’” remarks Cohen, who then instructed his team to “rip up” the 90-to 120-day plan, while accenting his new mandate for speed with the words “We’re going to do this now!” –Jack Sweeney