I’m not sure what kind of masking you got, but you do need to rub it down with the edge of a credit card or hard squeegee to activate the adhesive in a lot of the masking. (Small piece of acrylic works too.)
Be sure to do that…it can come up if you don’t.
If the cutting board is thicker than about half an inch, it will not fit on the tray…you will have to remove the tray and prop the engraving surface up into the correct range for the laser to focus on it.
You don’t actually have to do the measuring any more, but you do have to get the engrave surface into the correct range before you use the Set Focus tool.
You will also want to run the Calibration Routine before using it.
I’d also suggest you read everything at the Support button at the top of your browser before you start trying to use this for a business. There are things there that you need to know.