If I read the KB correctly, this is not supported by HockeyApp.
Per https://support.hockeyapp.net/kb/client-integration-ios-mac-os-x-tvos/how-to-upload-to-hockeyapp-from-mac-os-x ::
HockeyApp for Mac creates and uploads both the .ipa and the .dSYM file.
So the HockeyApp app itself opens the archive and uploads both separately. Even the dashboard page says:
Upload .ipa, .apk, and .zip files by dragging them directly on this page.
So if I understand the request, it's asking for HockeyApp to be able to take an Xcarchive, open it up and upload both?
I think that's beyond the scope of the plugin, but I will entertain reviewing a pull request for such a feature.