I worked for Mullenweg for a year at WordPress.com to write a book about all of these questions. It documents all the tools I used and what life was like as a remote manager of a development team.

http://www.amazon.com/Year-Without-Pants-WordPress-com-Futur...

You can read a free chapter about culture from the book here:

http://scottberkun.com/2014/why-culture-always-wins-an-excer...