Recently someone asked about the possibility of using SendGrid with Jiwa, attached is a copy of a plugin that will achieve this and works similar to the ones provided by Jiwa, all you need to do is provide the necessary API Key in the system settings.
The reason I ended up doing this is because I discovered an issue with trying to use the Outlook one inside a windows service such as the Rest API or the Scheduled Plugin Service even if the service is run as a given user in that it can't start Outlook, I am not sure if this is a one off problem to my machine or not.
Anyway the SendGrid one works with both, bear in mind that the normal security for approved senders under SendGrid still apply.