Try Voltage SecureMail and identity based encryption
Voltage SecureMail can easily send encrypted email to anyone.
Voltage SecureMail has Outlook plug-ins or you can use a web interface for sending encrypted email. Messages are completely controlled by the sender and recipient in their sent folder and inbox. No messages are stored on servers.
Recipients don't need any special software to decrypt and read their messages, just a browser. And recipients don't need to pay to read their email. In fact, they even get free support from Voltage. It's much easier to use than PGP, S/MIME or other older solutions...and just as secure...which is probably why they can afford to offer free support to their customers and recipients...unlike those other solutions.
I've used PGP and SMIME for years and rarely got non-techies to jump through the hoops to get private keys and certificates. Voltage SecureMail makes it a lot easier.
They have a free trial at:
www.voltage.com/vsn