I am working for Virtru, a startup building the "mom friendly" way to send encrypted email directly from your existing Gmail account (and others!). My Mom does not understand encryption at all, but has no problem using Virtru to communicate securely with some of her business co-workers.
Basically, it works like this (for example, with browser extension client):
1) the client generates a symmetric AES-256 key and uses that to encrypt the email locally
2) Gmail traffics the email to recipients normally, except the body of the email is now encrypted before it even leaves the client (the body also includes the unique id of the key, unencrypted)
3) the key is sent to a third party key store (Virtru) which controls access to the key based on identity (OAuth/OpenID)
It could be interesting to do some type of mash-up with Virtru and Keybase.io so that Virtru could automatically pull recipients' public keys and use a PGP type flow as opposed to the default of a symmetric key.
Happy to answer questions if anyone gives Virtru a try.
Basically, it works like this (for example, with browser extension client):
1) the client generates a symmetric AES-256 key and uses that to encrypt the email locally
2) Gmail traffics the email to recipients normally, except the body of the email is now encrypted before it even leaves the client (the body also includes the unique id of the key, unencrypted)
3) the key is sent to a third party key store (Virtru) which controls access to the key based on identity (OAuth/OpenID)
https://www.virtru.com/what-is-virtru
It could be interesting to do some type of mash-up with Virtru and Keybase.io so that Virtru could automatically pull recipients' public keys and use a PGP type flow as opposed to the default of a symmetric key.
Happy to answer questions if anyone gives Virtru a try.