The operator who keeps climbing the hospitality stack
Michael Greene runs Skylark, the New York luxury travel agency that refuses to pick a side in the oldest argument in travel - software versus humans. Skylark's answer, the one Greene now sells from the top chair, is deliberately ungreedy: technology when you want it, real people and expert advice when you need them. A booking site that behaves itself, and a phone number answered by someone who actually knows the difference between a good room and a great one.
That sentence sounds simple. Building it is not. Greene took over as CEO and President in 2024, inheriting a company that sells privately negotiated airfare and exclusive hotel partnerships to travelers who have flown enough to be hard to impress. His current bet is Wanderluxe, a members-only platform for last-minute luxury hotel deals - the kind of inventory that, until recently, only a well-connected advisor could shake loose. The thesis is that scarcity and service are not opposites if you build the right tools underneath them.
What makes Greene interesting is not that he landed the title. It is the strange, specific shape of the path that got him there. He did not come up through travel. He came up through dinner.
The dinner-reservation years
Before Skylark, Greene spent his career on the other end of hospitality's hardest table: restaurant reservations. At Resy he ran the Amex Global Restaurant - later Dining - Network, the program that quietly turns a credit card into a key for hard-to-book tables. Then he became Head of Global Strategic Growth, scaling the marketplace that connects diners, restaurants, and the people who want both to be happy at once.
Then he did the harder thing. In 2022 he co-founded Dorsia and served as its Chief Operating Officer, building the members-only reservation platform from inception - the team, the culture, the restaurant partnerships, the member base, and the pre-Series A funding that kept the lights on. Anyone who has tried to get a table at a restaurant that does not want to give you one understands the problem he was attacking. Dorsia turned that frustration into a marketplace.
After Dorsia he served as Chief of Staff at Avero, the hospitality-analytics company - a step into the numbers behind the rooms and the tables. Each move was a rung. Reservations, growth, founding, operations, analytics. By the time Greene reached Skylark, he had assembled an unusually complete tour of how hospitality actually works when nobody is looking.