It's a challenging time to find service providers for pretty much anything. If the guy plowing your driveway works for someone else, he may be a new hire and won't learn what not to do unless you provide some feedback.

Since the pandemic I get ghosted all the time trying to find new tradespeople, they show up for a quote then never come back, over and over.

On the bright side, maybe the driveway is one of those things you can do yourself with some modest equipment (a snow blower, or whatever). One thing is always true, nobody you pay is going to give it the same level of attention as you. Corners will be cut (literally, off your yard and plantings), messes will be made, sometimes if you want it done right you have to do it yourself.

Good luck. My driveway service had new blood this year who we really messing up. Three calls later and some additional stakes in the driveway and finally the mess has ebbed.