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.
Do you recommend this book to understand remote working dynamics at Wordpress ? Learning from companies that succeeded in setting up the remote working practice is definitely the best way to understand if you can put the process in a bottle.
Anyway thanks for sharing this title.
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...