Phil Zimmerman whas very positive about PGP.
I remember talking to him during www.hal2001.org
But after 9/11 he started having doubts about PGP when it came out that terrorists had been using it to send encrypted mail.
The new CTO is a good replacement since Jon Callas has worked for PGP in the past and is a classic Apple engineer.
Check out his website www.merrymeet.com