As mentioned in my support ticket response to you, the general process would be:
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Install Certify The Web on your server (the free version will work fine for this evaluation)
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Acquire your certificate (using either http or DNS domain validation): Requesting a Certificate | Certify The Web Docs
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Add a deployment Task (most likely the powershell scripting task) with your own custom script to apply the SSL certificate to your server (in this case, MailEnable). Scripting | Certify The Web Docs - you can run your task repeatedly to develop/test it without re-requesting your certificate. You will want to apply the SSL configuration changes, then you will probably want to restart the MailEnable service (as per this example).