Employment Law Questions? Ask an Employment Lawyer.
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Your boss can employ the services of an independent contract sales person. Your boss can convert the employee to an independent contractor. Your boss can create a contract which specifies the terms of the agreement. It should clearly document the payment structure. Your boss cannot control the methodology of how the work, and cannot provide the benefits an employee gets e.g. insurance, time off for holidays etc. Your boss would need to produce a 1099 for the amount paid.
Your boss should discuss the possibility of needing separate insurance to cover his risk around the contractor's activities with his insurance carrier..
The IRS may have an issue since he was an employee doing exactly the same task. You may need to show that other than paying for the sales activity no other relationship exists. Your boss should speak with his accountant to make sure he does not run afoul of the IRS . You can look at the following which the IRS has to help with determination of status: http://www.irs.gov/pub/irs-pdf/fss8.pdf
If your boss's motivation is to eliminate liability, hiring an independent contractor may not solve the problem.You generally aren't liable for injuries your independent contractor causes while working for you. However, If your boss knowingly engages an individual with a problem that could cause harm to another he may not be able to hide behind the fact the person was an independent contractor. There is a tort for "Negligent Hiring" which your boss may be liable for.
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