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If there is an employee uses the internet through an internal proxy in his company, and he use a paid VPN service to browse safely, can IT side be able to monitor his behavior?

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If he connects from his computer to the VPN, the company can't see what is happening within the VPN connection unless they have monitoring software on his computer (which for some types of VPN clients, may include simply having their own trusted certificate to allow MITM attacks). Only his computer has access to the details of the encryption for the VPN tunnel. The company would possibly be able to tell that an encrypted connection was being used though.

  • Note that monitoring software could be something like adding a default, trusted root certificate that the company created, allowing them to act as a physical-network CA, meaning that the company can perform man-in-the-middle attacks. You'd need to have the correct certificate pre-loaded (and verify it wasn't replaced automatically). – Clockwork-Muse Jun 4 '14 at 12:00
  • @Clockwork-Muse - good point, I was thinking of clients that included the certificate for the connection with the configuration of the connection, but not all VPNs do that. I have updated my answer to make sure it points out the trusted MITM scenario. – AJ Henderson Jun 4 '14 at 13:16
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If he uses a vpn to browse, monitoring software can only record the keystrokes he typed on the keyboard, but it can't track what websites he has visited.

  • Actually it can; the company can enforce screen capturing software, or even a browser extension that traps all data. – ndrix Jun 4 '14 at 4:52
  • Or install a trusted certificate they created, allowing them to act as a root CA on their physical network; this would allow them to perform man-in-the-middle attacks trivially... – Clockwork-Muse Jun 4 '14 at 12:03

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