When John Santora became CEO of WeWork, the company was emerging from bankruptcy, saddled with one of the most notorious failures in business history. The longtime commercial real estate player is leading the company's next act: proving that flexible work can be a disciplined, profitable business.

As part of Business Insider's The Long Play, Santora shared what it takes to turn a damaged company into one built to last and offered insight into a real estate market being reshaped by how we work now.

He also talked about how AI is affecting real estate with Cadie Thompson, Business Insider's deputy news chief and executive editor.