Not a great plan. You could have applied for a change of status to B-2.
However, you won't be precluded from obtaining H-1B status because of your overstay.
Mr. Shusterman is a former INS Trial Attorney (1976-82) with over 35 years of immigration experience. His response to your question is general in nature, as not all the facts are known to him. You should retain an attorney experienced in immigration law to review all the facts in your case in order to receive advice specific to your case. Mr. Shusterman's statement above does not create an attorney/client relationship.
If the H-1B petition is selected and approved, then you would need to return to Canada and reenter with the H-1B approval notice. As a Canadian national, you would also qualify for a TN. You should consult with an experienced Immigration Attorney.
Staying beyond your authorized was not a smart decision. Assuming you depart the U.S. before you accrue 180 days of unlawful presence will mean you are not subject to the three year bar. That being said, a visa may still be denied as a matter of discretion due to the overstay. You need to depart before November 7th.
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