Bob uses BitLocker to secure his data. When he uses Carbonite, he sees that his data is unencrypted when restoring it. Leo says that as long as he's logged in, Bitlocker has unencrypted the data. And when he logs out, it encrypts it again. But the good news is that when he backs up to Carbonite, the backup is encrypted.
Carbonite will allow him to make the data completely encrypted, and he can change that in the settings. Using BitLocker requires certificates, though, so he should make sure they're backed up. If they get corrupted, he'll lose the ability to access his encrypted data even if he knows the password.
There's also a good program called SpiderOak. It works like DropBox, but uses end-to-end encryption.