Yes at sentencing you need to request it, and it is conditional on the jail in the county that you are transferring accepting you. The county receiving can decline. You must apply so contact the Huber program before you start serving your sentence.
This is not intended as legal advice. It is only provided for educational purposes and cannot be relied upon as legal advice. Further no attorney client relationship is or has been formed by answering this question.
If work release means release from jail in the morning and return to the jail at night, probably not. Jail sentences must be served in the county where the sentence is ordered. If work release means a monitor then, probably yes. Judges would rather you keep your job. Ask the judge or your lawyer before you are sentenced.
These situations come up often, and usually can be resolved in a way that will allow you to serve your time while still going to work. Ask during your sentencing to be able to serve the time in another county. The judge will likely allow for it, and give you time to make those arrangements with the other county. In fact, you may want to contact the jail sergeant in the county where you want to serve the time to find out if they have a bed available and if there is anything else they need in your sentencing order to make this happen. You may be required to pay a higher daily fee for doing work release in another county as well.