Yes, you can do that. Follow the below instructions to set that up on your Quick Keys, Tablet button, or a button on your pen.

Before you start this process, it would be helpful for you to use File Explorer to locate the .exe file first so you know where it is located. You will need to browse it in just a minute. 

You can set this on a button on your Quick Keys, your Tablet, or your pen.

In this example, I'm setting it up on button 8 on my Quick Keys.

[1] Select the button you are wanting to use. I selected button 8.

[2] I then selected Application from the drop-down menu.

[3] And then select Open/Run

[1] Select Browse to locate the .exe you are wanting to have opened. In this case, I'm adding CMD.exe.

The challenging part will be to find the .exe you are wanting to run.

[1] This shows the Path I used to locate CMD.exe

[2] Once you find it, select it.

[3] And it was placed in the File name field.

[4] Then you can click OK

[1] You can see it as being added to button #8, and on the Quick Keys, you will see it displayed as cmd.

[1] This is what it looks like on your Quick Keys.

You can use this process to set up any .exe on your computer, as long as you can find the command line exe.