Virtru engineer here. Very excited to see Virtru included in the list!
As you say, there is always a balance between security and convenience. Virtru tries to make it as easy as possible to send encrypted email. We do this by integrating with your existing email client (eg, Gmail) so that you can send encrypted email from your existing email address with the tools that you are already familiar with. All you have to do is click a switch to turn the security on and then compose your email as you normally would.
One reason that some consider email inherently insecure is that the metadata (to/cc/bcc, subject line, etc) is not protected even when the message content (email body, attachments) is protected. It is critically important to define the term “secure”. One must understand both what they are trying to protect and why, and what the tools they are using actually do protect.
There are many use-cases in which the goal is to secure only the message content. For example, someone emailing their lawyer about a case, doctor about an appointment, or accountant about their tax filing. Also, consider a business sending sensitive intellectual property to its partners or even its own employees. In these examples, the sender may not care about protecting the fact that they communicated with the other party, but they certainly want the message content (personal, financial, sensitive, etc) secured so that it is shielded from prying eyes.
Obviously, there are many other use-cases where protecting the metadata may matter a great deal. In that case, one must consider their goals and make sure that the tool being used meets their criteria. If completely anonymous communication is the goal (protecting both who is talking to whom and what is being said), then email may not satisfy the requirements (certainly not in its current implementation).
I think that many would agree that email is here to stay for the foreseeable future. It is pervasive and the de-facto communication platform, especially in business settings. I think there is great value in individuals using tools which implement end-to-end encryption to increase the security of the emails they send so that the message content can only be read by the intended recipients. This protects the email both in transit (eg, routing from SMTP server to SMTP server) and at rest (eg, sitting in a user’s inbox on Yahoo’s server).
Do you think the general tech community appreciates the distinction between the degrees of “security”? Often, I hear the “all or nothing” mantra, which I think can impede the adoption of reasonable email security tools depending on the goals trying to be met. Thoughts?