The business-casual dress code had Troy Freeman stumped. As the long-time CEO of Otto Hotels &
The business-casual dress code had Troy Freeman stumped. As the long-time CEO of Otto Hotels &
Resorts, now the second-largest lodging company in the world, he’d packed for hundreds of work
trips before, but suits were his go-to. Without them as an option, he was having a much harder time.
His flight was leaving first thing in the morning for Carmel, where he would meet his newly
expanded executive team for an offsite to discuss the company’s portfolio strategy. The facilitator,
Caroline Dvorjak , was a marketing professor and a seasoned consultant.
Otto had just finished a $9 billion acquisition of Beekman Hotels, which meant it now had nearly
4,800 hotels and just over a million rooms in 100 countries. Like most of the big hoteliers, however,
Otto owned few of those properties; instead it franchised and managed them, with the bulk of the
real estate owned by independent companies that licensed Otto’s brands. The addition of
Beekman’s eight brands had increased the number now under Otto’s umbrella to 21. The question
on everyone’s mind, especially investors’, was how Troy would manage this much larger portfolio,
given the overlap between existing and acquired brands in terms of positioning, price tier, and
geography.
During the deal discussions, Otto’s board had encouraged Troy to remain noncommittal about its
post-merger strategy. He’d once commented on an earnings call that Otto “probably” didn’t need all
