To enter the US, you need to have a valid Visa stamp for the purpose of the trip. To change status, the evidence submitted with the application to change status must show that you are in valid status on September 30th.
Your employer needs to retain an experienced immigration lawyer to review all the facts, advise them, and handle the case. Your employer can find one through http://www.ailalawyer.com.
J Charles Ferrari Eng & Nishimura 213.622.2255 The statement above is general in nature and does not constitute legal advice, as not all the facts are known. You should retain an attorney to review all the facts specific to your case in order to receive advise specific to your case. The statement above does not create an attorney/client relationship. Answers on Avvo can only be general ones, as specific answers would require knowledge of all the facts. As such, they may or may not apply to the question.