Hey @archimesta1983, welcome to the Cayenne Community.
You shouldn’t have to do anything on the iPad itself to enable SSH, just follow the instructions above to make sure it’s enabled on your Pi.
Keep in mind that if anyone reading this thread is having trouble with the app connecting to your Pi via SSH, you can just skip this by installing from Add New > Device/Widget > Single Board Computers > Raspberry Pi > Option 2 on the web dashboard as well. This will give you the commands that need to be input into the Pi so you can do it manually.