I have some outdoor lights that are controlled by this hard wired switch. There are multiple transformers wired into this switch. How can I automate this? I don't even know what to search for here.
Thank you in advance,
-Matt
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Typically that's a weatherproof cover.
Behind it you'll find a regular toggle switch.
Which means you can replace that with a Z-wave/Zigbee toggle switch. However, those transformers are an inductive load and you need to choose wisely, not all smart switches live happily with inductive loads.
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Thank you so much. It didn't even cross my mind it was just a cover 
I'll take it apart this evening and make sure. Again, thanks for the help!
-Matt
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Aside from the inductive load concern, the other potential gotcha may be that metal cover (with respect to signal reception), but maybe it's plastic?
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Would that cover even work with a smart switch? Don’t most smart toggle switches just momentarily up/down.
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That cover is just a lever on the inside that moves the switch. If the smart switch goes to center, then presumably the lever in the cover will go to center.
You’re probably right, but if the lever is detented or anything it might cause an issue. But since it would only move when operated manually it would just be something to keep in mind.
Hard to tell exactly, but it looks like the switch is mounted to a wood piece under the weatherproof cover.
Which in turn is nailed to the wall... 
Would putting something like this in behind the mechanical switch work if wired correctly. Or maybe one in front of each transformer all signaled off that switch in parallel.
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In theory any on/off smart switch (one with electromechanical relay) may be used with inductive loads but external snabber (arcing suppressor) must be added. Smart Switches rated for the inductive loads have this stabber built-in.
Well, that probably makes two of us on this topic that understands inductive kickback and using a flyback diode or snubber. 
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Maybe you want to at least consider if you want to automate the lighting circuits or the output of the multiple transformers? All or none might be what you want, but while you are mucking with it maybe there is an option to improve the setup?
Most home automation devices are not designed for outdoor service (wet locations). You can always replace the existing switch plate with another type of wet service plate, including using one that is made of plastic. Or you can get a clear, waterproof cover.
Make sure that the device you use is a switch with a relay rather than a dimmer.
Three, but who's counting?
I have a post way back about adding a snubber to a bath fan smart switch where I was blowing up switches fairly often. After I added that circuit, the switches were fine.
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You mentioned transformers, are they for landscape lighting?
If so you can do what I did with mine, I installed Sonoff zbminis inside the case of each transformer. You then don't have to worry about the switch. Just leave it on all the time.
Second option is to install a ZBmini inside the light switch box and use the existing switch/waterproof cover to control the zbmini.
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