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One legal issue you can run into with benefits is that you can't offer a benefit to one employee and not offer to the next. Obviously they have to go through the probation periods, etc... What I am talking about is paying for one employees insurance and then not paying for another's after they have met your pre set criteria for obtaining benefits. You run into discrimination issues this this scenario.
You can do it to some degree with a written employment contract between the company and certain employees.
For example, my operations manager gets additional benefits not listed in the company handbook. However, we have had to set up an agreement with him stipulating the terms and the agreement of both parties. If I just went and gave him additional days off, or paid for his families health care without such an agreement, then it legally opens up the wrest of the company to be eligible for the same perks. It is all a legal game and should not be taken lightly, one upset employee could make your day real bad, real quick.
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Matt
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