CEO Lets His Employees Work Whenever They Want–From Wherever They Want

Beyond that, going fully asynchronous becomes a huge disadvantage to anyone trying to accomplish something that requires cross-team or even multi-person collaboration on a reasonable timeframe. The amount of round-trip back and forth communication that slows everything down can become staggering in no time.

On small, tight-knit teams this is largely mitigated by everyone's willingness to jump in and help synchronously when necessary. Once you grow to the point of a big remote organization where people don't really know each other, it just becomes a game of dodging questions and delaying responses until the other person solves their own problems. The more engaged you are, the more work you end up taking on. Some (sadly, many) people see this as an opening to make themselves as scarce as possible and only do the neatly packaged work that comes directly from their managers. As a manager, you end up mediating all sorts of communication issues that would simply disappear if the team had some core working hours.

The development of Linux is an example of large scale work that is successfully performed mostly asynchronously.

CEO realised the game has changed, offers flexible working in order to retain talent.

In Support you are given set scheduled hours.